my fiancé was my boss’s bully in high school

by Alison Green on March 4, 2025

A reader writes:

I am to be married next year and decided to send out save-the-dates early. I really like my coworkers and my boss and wanted to invite them to the wedding. When my boss received my save-the-date, they swung by my desk to congratulate me and we got to chit chatting. The conversation led to my boss asking to see a photo of my fiancé as they had never met before. I showed them a photo from my engagement and —

It was like the smile literally slid off their face. I asked if they were okay, and all they said was: “Is this who you are marrying?” I was really confused and had a very bad feeling.

I went home that night and asked my fiancé why on earth this person would react to his face in such a manner. My fiancé claimed to not remember them, but clearly he recognized them. After a huge argument, he revealed that he was a prankster in school and may have sometimes involved them in “pranks.”

I’m not stupid, I can read between the lines. “Pranks” are only funny when everyone is laughing and based on my boss’s reaction, it was clear they never found these pranks funny. We had another huge blow-up and only when I threatened to walk out did he reveal the full extent of these pranks, all the while telling me “he wasn’t this person anymore,” etc. etc.

The pranks were horrific, atrocious, and not funny. Once, on a dare, he and his friends took pictures of my boss in the gym locker rooms and plastered his naked pictures all over the school. This is just the least horrific thing him and his friends did. I’m disgusted that the man I love and want to spend the rest of my life with could ever be this person.

I returned to office the next day and requested to meet with my boss. My boss wasn’t in the office, and in fact took the next two days off. When they returned to work, they did not really engage with me or even look in my direction.

Now I am unsure what I should do. My engagement is almost over. There is no way I can marry my fiancé now that I know what he is capable of. I’m humiliated. I don’t have any friends who aren’t his friends too. My parents are telling me to move and find another job and marry my fiancé because he is rich and treats me well.

I’m unsure of how to navigate the situation at work, given that my boss really doesn’t want to engage with me. Any advice you can offer about the personal aspect of this situation will also be really appreciated.

First, full disclosure: something about this letter pings my “is this real?” alarm. Apologies to the letter-writer if it is; life is often stranger than fiction. But even if it’s not, it’s useful and interesting to talk about how to handle it if it turns out your boss has a history with someone important in your life. With that said…

A lot of people were very different as adolescents than they are as adults. A lot of people behaved badly toward others in their youth but learned from it, regret their behavior, and have resolved to be better people now. The troubling part to me is less that your fiancé was an asshole in school and more that he’s minimizing it now. If he originally didn’t come clean because he was ashamed, that’s one thing (although still not great). But if his position is that these were just youthful hijinks and no real harm was done and you shouldn’t be upset about it now, that’s about his character now.

And if the best argument your parents, who presumably know him, can come up with for staying with him is that he’s rich and treats you well … that’s really not good. (It’s also fairly insulting to you, as if that’s the pinnacle of what you could expect in marriage.)

You said you’re humiliated, and you shouldn’t be. You learned something about your fiancé and decided to act on it before binding yourself to him for life. There’s nothing humiliating about that. If anything, there’s admirable strength in knowing that sending out save-the-dates doesn’t obligate you to move forward with an enormous decision that you no longer believe is right for you, something not everyone has the wherewithal to do.)

As for the work stuff, you really have two options:

1. You can make a point of acting aggressively normal with your boss and just give them some time to get back to normal with you. Sometimes when you’re doing this it can help to go out of your way to find opportunities to have normal interactions, so that their most recent associations with you are normal work things rather than whatever was going through their mind when they saw that photo. Also, if you do call off the engagement, make sure your office (and therefore your boss) knows.

2. You can address it head-on. Set a meeting with your boss or raise it next time you’re one-on-one and say, “I saw the reaction you had to seeing Bob’s photo and when I asked him about it, he was evasive but I learned enough to understand he was a jerk in school. What I learned through this conversation about his character now was enough for me to call off the engagement. I’m sorry if that photo was an unexpected shock. I’ve always valued my working relationship with you and I hope we can move forward without letting him affect that.”

I lean strongly toward #1. I have a high tolerance for awkward conversations if they’re in the interest of getting everyone on the same page, but there’s a very good chance that #2 won’t be necessary after some time goes by … although you could keep it in your back pocket to use if things aren’t back to normal a few weeks from now.

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    1. Antilles*

      Have you considered that the fiance is wealthy, treats OP well, and only treats other people like crap? Clearly this clears the very low bar the parents have for spouses.

      1. KHB*

        I wish I could remember who I got this from, but: If someone is nice to you but is a jerk to everyone else, you’re not special – you’re next.

        4. Roy G. Biv*

          “If someone is nice to you but is a jerk to everyone else, you’re not special – you’re next.” This is going in the AAM quotes file.

        6. CJ*

          I remember reading that on Captain Awkward (or some phrase with the same meaning) and having to sit with it for a while.

            1. Chick-n-boots*

              AAM and CA are my two favorite advice sites/columns and nearly all of the quotable advice I hold near and dear to my heart are from them. I’ve always loved how much crossover there seems to be between the readers/commenters on both sites (not to mention the actual crossover “events” that Alison and Jennifer have done!)

        8. 2 Cents*

          I could give this to my BFF who’s going through a divorce. “He treats everyone else this way but not me” until the day it was her and WORSE than everyone else.

        9. 40 Years in the Hole*

          This was absolutely a former (civilian) boss of mine. She was a hired gun brought in to “pink slip” several employees. Then the director made a case to TPTB to create a HR position and she was hired directly into it.
          From the get-go she allied herself with the senior command & surrounded herself with sycophants/weak staff. Always gossiping or criticizing regardless of rank/status/experience. Then I got assigned to her. Nice as pie to me – until she wasn’t.
          She still lives in a very small, tightly locked trunk in the nether regions of my psyche.

            1. Csethiro Ceredin*

              Ha, yes! My brain made a tire screech noise and I read it twice before finishing the sentence.

        14. Rainy*

          That one’s the flip side of a thing I say a lot about toxic groups, which is “no one loves a scapegoat like the enabler who knows they’re next”.

          1. Marion Ravenwood*

            Suddenly a ‘friendship’ group I had in high school makes a heck of a lot more sense.

        15. Oniya*

          There was a bit of advice I read a while ago: Watch how your (date/partner/etc.) treats service people – that is to say, waitstaff, cashiers, parking attendants, and so forth. These are the people that rely on customers to get their paychecks, and therefore have to put up with more crap.

          If your partner is a jerk to these people that have to deal with them, they are not a ‘nice person’.

          1. AF Vet*

            Yup. That’s also a common gut check for business lunches / dinners, etc, when you’re the one being pursued or flattered into joining. How do they treat the restaurant staff when they’re in their good behavior mode?

      2. Pastor Petty Labelle*

        Yeah I mean he treats OP well NOW. That is totally a reason to stay with him. Because that will never ever change, even if OP disagrees with him on some issue.

        1. FricketyFrack*

          And only barely – the second she brought up something he didn’t want to talk about, he turned it into a fight, so I think the timer on “treating her well” might be about up.

          1. Teapot Connoisseuse*

            I reckon the timer expires the minute she’s legally bound to him. Run away, OP!

            1. Rainy*

              He might have the self-control to wait until she’s pregnant. They often don’t, but that’s no guarantee.

          2. goddessoftransitory*

            And he minimized and truth-trickled until she threatened to walk out, then tried to say sexual violence against a peer was “just a joke.”

            LW, you calling off this engagement is the smartest thing you have ever done.

            1. Hey, I'm Wohrking Heah!*

              Oh Lordy, I read “truth-tickled.” Thanks for the inadvertent laugh.

        2. Your Former Password Resetter*

          It can be an argument to stay there for now. Maybe it’s a bad time for the OP to throw a breakup/moving into their life right now.
          But I would definitely make a backup plan in case that doesn’t work out.

        3. Kella*

          And “treating OP well” right now includes lying to her face and avoiding accountability, so…

        4. Reluctant Mezzo*

          Yes, if you’re going to marry James Potter, it would be a good idea to find out how close his friends are and how fondly they remember those past days.

          1. Kiriana*

            Oh god the way I cackled. Even when I was in that fandom I didn’t like literally every major character. (I also didn’t like the writing or the worldbuilding, it’s really hard to remember what I *did* like about it when I think back…)

            1. gregor_vance*

              For me it was the worldbuilding! Hogwarts was such a fleshed out place to my adolescent brain. But the characters weren’t great (other than Snape) and there was very little growth with any of them. The plotlines and writing wasn’t great. The last book was an awful mashup of every British fantasy author.

              But Hogwarts…I got lost there.

              That said, I’m not sure when or if I am planning on introducing those to my kids.

      3. Amber Rose*

        I like that trope in romance, I have to be honest.

        I do not like it in reality. Unless you are the Cold Duke of the North you do not get a pass.

          1. goddessoftransitory*

            And even in Jane Eyre she didn’t marry him until the roof literally caved in on him.

        2. Nobby Nobbs*

          Well, in fiction you (reader you, not character you) can be a lot more sure that what you see of a character is what you get. In real life you do have to extrapolate a person’s character and future behavior from how they treat other people. What a drag.

        3. C*

          Fictional aholes are great, just so long as they have a hidden pain.

          Real life ones are terrible, pain or not.

          1. Inksmith*

            what’s that joke a out how, in real life, they need someone following them around narrating their thoughts/emotio s/backstory?

        4. Kiriana*

          Ugh, someone can be as wonderful as is possible for a person to be under the surface, but if I have to fight through layers and layers of asshole bullshit to earn the right to find that out it’s not worth it.

      4. Boof*

        The structure, particularly that hook at the end does remind me a of a lot of Reddit likely “engagement baiting” AI threads.
        That being said, as an exercise in taking LW at their word and/or helping someone who is in a somewhat similar predicament; LW only you can decide if you want to spend the rest of your life with this person; your parents, friends, community etc may factor in to how much support you have overall, but you are the one who has to live with this decision, and if you decide it is a terrible decision and/or there’s other red flags about how they will treat you and/or others, you can advocate for yourself even if it goes against everyone else’s wishes/plans. LW, only you can discuss with your fiance if they are really a different person now and if so, why they didn’t own up when you first brought it up, and what kind of trust violation that is between life partners. Only you can decide if their answer seems genuine. Fortunately you have some time to figure this out.

        1. Reluctant Mezzo*

          Also, it would be a good idea to find out if his friends who participated with him are still close and if they think it would be fun to play ‘pranks’ on you. ROSE MADDER is all too true for some women.

        2. MigraineMonth*

          However, there is probably never going to be a time when it is simpler to walk away. If you go through with the marriage, acquire joint property or have children together the legal, financial and social consequences of leaving him are only going to get higher.

          Don’t go through with the wedding if you aren’t certain this is the person you want to spend the rest of your life with *and* that they will treat you well even if that changes.

      5. Ellie*

        Other people will include OP once he’s got her locked down. And her family. And their kids.

        OP – I knew a woman who left her fiancé 3 days before the wedding. She never said why, although he was originally from overseas, and his family had all flown in only a few days before. I assume someone told her something, much like what happened to you OP.

        She got over it. She lost tens of thousands of dollars, but she took her mum on the honeymoon with her, and had a lovely holiday, and has since met and married another man. You can do that too.

        I wouldn’t worry at all about your boss. If you’re intending on leaving anyway, word will get around.

      6. Spaypets*

        Alison, I am so glad you mentioned wondering if this question was real. It set off my spidey sense as well. It very much sounds like a story line in a TV show or movie.

        Apologies to the LW if I am wrong. I am sorry you discovered something so awful about your intended.

    2. not nice, don't care*

      Wealthy dudes who like to treat others poorly usually believe a marriage license is a bill of sale.

      2. Momma Bear*

        I was thinking same.

        Also, if this is true, I’d sit and think very carefully about how he responded when confronted and how he treats people. Was he sorry about the past or just sorry she found out? Most of us do stupid (or worse) things in our youth but good people take accountability. That will tell OP how to go forward. Parental support or not, this is OP’s life and wealth is not everything.

  2. juliebulie*

    I like option 2 better, to tell the truth. The boss suffered actual trauma at the fiance’s hands. Acting “aggressively normal” might seem callous.

    1. Targ*

      Agreed, you don’t want to seem like a foolish person who’s willing to tie themselves to a cruel person. Be aggressively, heartlessly self interested in how you fix this, OP.

      1. MigraineMonth*

        I think that the smartest *and* most respectful route is to take one’s cues from the boss.

        The boss *did not* confide in OP about the bullying. They stopped smiling when they unexpectedly saw a photo of their HS bully, but they chose not to even tell OP that they knew the fiancé. They took several days off work, and ever since then the boss has been avoiding meeting the OP one-on-one.

        I think the last thing in the world the OP’s boss wants is to talk to one of his subordinates about his high school trauma, and OP should respect that by not bringing up the bullying or acting strangely around him. If he has concerns about her judgement, they will probably be put to rest when the office learns she has cancelled the wedding.

        1. Ellie*

          Her boss is probably tying themselves in knots over whether to tell OP about the bullying. From their point of view, they don’t know OP already knows. I’d expect hearing that the wedding got cancelled is going to completely put this to rest.

          1. Kyrielle*

            Yup. I would make sure he finds that out. Unless he brings up his reaction, though, I wouldn’t talk about it beyond that. (If he does, I might thank him for reacting that way – he didn’t do it as a service to the OP, and it sucked for him, but it sure worked out to be good for the OP in terms of information!)

        2. Chick-n-boots*

          I absolutely agree with the sentiment of your recommendation but on a human level, I think I would have a really hard time not saying SOMETHING. Maybe if the LW feels that way but also doesn’t want to make this too awkward for the boss they can send them an email letting them know that they weren’t sure if the boss would want to talk about it and wanted to respect that, but that they had learned some things about their fiance that made them realize they weren’t someone they wanted to spend their life with so the wedding was off and they were grateful to have learned these things now. They can offer to talk about it further if boss would like, but otherwise they are happy to just leave things there. Maybe also throw in some words about how much they like working for boss and value their relationship or something?

          I don’t know. Maybe that’s selfish and the wrong thing to do and I can’t decide if I’d want to do that because I wanted the boss to know that I appreciated knowing what I knew and that I felt good about making the choice I did (lest the boss find out they cancelled the engagement and feel “responsible” or something for inadvertently hurting someone they otherwise were clearly friendly with) or if I wouldn’t want to leave the boss with the impression that I was the kind of person who would be totally OK marrying a person who would do what the fiance had done and then tried to lie about it/downplay it as an adult.

    2. Never the Twain*

      +1.
      I’d take [any sort of] “normal” without a mention as meaning ‘What, that? It was nothing.’

      1. Beth*

        I don’t think that’s a fair assumption given that the boss didn’t tell OP what happened! He just had a somewhat weird reaction to a photo. Most of the info OP has, she got from her fiance, and her boss has no idea she knows it.

        Given that, I think there’s a lot of room here to act aggressively normal and have it be a fine (or even preferred) outcome. Her boss might take that as “She has no idea about the bullying and doesn’t know why I was so weird for a few days,” and that might be a relief, to believe that no one at work knows about his worst childhood experiences. Or, he might take it as “She knows something but maybe not the whole picture, and she doesn’t want to make me talk about it at work,” which would open a door for him to bring it up or not as he prefers.

        There’s also other context than just the presence or absence of a conversation about it. If OP calls off the wedding and breaks up with her fiance, that’s major office gossip material. Her boss will hear about it without her taking him aside. Given the timing, it’s not a stretch to wonder if she asked her fiance about her boss’s reaction, found out about the bullying, and ditched him over it. He probably doesn’t need to be told that his reaction triggered the breakup to connect those dots. (And in fact it might be better not to tell him that–even if everyone agrees it’s for the best, what an awkward thing to have on your shoulders!)

        1. linger*

          Maybe Boss is avoiding contact while considering (and probably rejecting, since it’s personal and also advice not typically well received) whether to disclose the bullying and warn OP off the marriage.
          In which case, OP sharing that they’ve broken off the engagement might be all that is necessary.

          1. Walk on the Left Side*

            I have to say, I’m interested in the thought exercise of what the advice would be for the manager in this case! Being faced with whether or not to tell an employee something like that and, as you say, warn them off and/or ruin their engagement…or to have them find out later that you didn’t warn them…it puts the manager in a really difficult situation too in addition to bringing back the bullying trauma.

            1. linger*

              If Boss had written in, we’d have more detail of their thought process to work with. That could well change the advice for Boss; less clear whether it should affect our advice for OP.
              (Yeah, it’s a common dilemma: if you Know that someone is Wrong for a friend, do you speak up — which risks that advice and that friendship being rejected — or do you wait it out? But that’s a dilemma for friendships, not so much for professional relationships, and especially ones with a status imbalance: both aspects should see Boss err towards butting out.)
              Without more clarity on Boss’s POV, everything’s speculation. (See threads re: Boss’s level of revisited trauma, (i) which isn’t OP’s problem to deal with, and (ii) best-case scenario is we can assume Boss knows that too.)
              I think the best we can say for OP is that, probably, OP should have some kind of conversation with Boss, but also, OP should not go into Boss’s own history (respecting that Boss has avoided sharing any details).
              Hence my suggestion that most likely, all Boss needs to hear is that OP is no longer involved with Bully. How specific a reason, if one is given, could be anywhere between “it didn’t work out” to “he wasn’t who I thought he was”.
              It can’t be tied to anything about Boss’s history with Bully.

    3. Chilli Dawg*

      Yes, I agree. If the LW considers the engagement/relationship over, I would be up front with the boss that you were appalled by what you learned about your partner.

      1. Reality.Bites*

        Yes, if only to erase any doubts the choice of fiancé raised in the boss. I’d go so far as to thank boss for speaking up and ending up saving OP from a disastrous marriage.

        2. goddessoftransitory*

          I agree. He really pulled her back from a very dangerous brink. He could have said nothing, but he didn’t.

          1. Manic Sunday*

            He DID say nothing! Well, he asked for confirmation that the man in the photo was OP’s fiancé, but that was the end of it. His facial expressions gave OP a clue something was wrong. It seems like he really tried to avoid saying anything negative about his employee’s fiancé, which was the appropriate, professional thing to do in the moment. I’m inclined to think he can be trusted to react calmly to OP initiating an honest conversation now.

            1. MigraineMonth*

              Except he’s been avoiding her. I imagine he emphatically does not want to talk to her about his adolescent trauma. I don’t know if his opinion would change if he knew that she dumped the fiancé, but how many of us would want our traumatic experiences brought up at work?

        3. MSD*

          But the boss didn’t speak up. If I were the boss I would like to continue the delusion that my employee didn’t know all of the horrid things that were done to me in high school. I would be very anxious that the OP would want to discuss them with me. Even just apologizing for the fiancé or acknowledging he was a jerk would be way too personal and upsetting/triggering for me. If the OP breaks up with their fiancé don’t give a reason. Just say it didn’t work out.

      2. Paint N Drip*

        and also I would specify that you are seeing your fiance differently but your perspective on your boss has not changed
        I can imagine as a bullied person, you would might feel some shame that people in your ‘new world’ (life after bullying) might now view you in a negative light, which is almost universally untrue but our pain can be a liar

        1. Not that other person you didn't like*

          As a victim of school bullying myself, THIS THIS THIS.

        2. lazuli*

          Yes. This would be why I would hesitate to talk one on one with your boss about it. They’ll have no idea what your ex told you and I wouldn’t want to make them worry you’re going to laugh at them, even if you never would.

        3. linger*

          But Boss does not officially know that OP knows anything about the bullying.
          Because Boss has shared precisely nothing.
          So it’s safer for OP not to mention that at all.
          Yes, Boss’s reaction actually was a catalyst for the conversation, argument, and breakup;
          but the breakup was about the kind of person Fiance is *now* (minimising and excusing the bullying behaviour; i.e. still unapologetically a bully).
          If Fiance had changed, that conversation could have gone quite differently. And then maybe OP might have had to explain the continued relationship to Boss. But, as things stand, there is no need to go there. Or to mention Boss’s history with Bully.
          OP can say they’ve broken up. And maybe add that they realized something about the kind of person Fiance was. (And even that much is probably oversharing, but it will be sufficient to validate Boss’s own feelings about Bully. Boss will not need any more detail than that.)

    4. Judge Judy and Executioner*

      I agree. If she is definitely breaking up with her fiance, option 2 shares that she is no longer marrying her boss’s bully and that the boss’s reaction helped expose the bully, resulting in his engagement being broken off.

      2. Elbe*

        Agreed. I’d at least like the boss to have the satisfaction of knowing that this guy’s actions caught up to him, and that other people are horrified by what happened.

        1. goddessoftransitory*

          It might go a long way towards silencing jerk brain whisperings about how he’s still hung up on this and no one ELSE thinks it’s a big deal, jeez! to hear that a normal, regular person was so horrified she called off her engagement. It was that big a deal.

      3. Rapunzel Rider*

        Maybe just a me thing, but if option 2 is taken be sure to be be VERY clear that the break up was due to fiance’s response and not leave boss with potential guilt that OP might partially blame them. Obviously good for all parties for everything to be out but I know, if I was in boss’s shoes, and someone told me that they were ending a serious relationship because of something related to me (even if I did nothing wrong and like in this case, it is all on the ex) I would feel guilty for causing them major life change and loss of what good things they saw in them (because there had to be a reason they were getting married before the truth came out). Grateful they took it seriously and would definitely have a deeper respect for them as a person but don’t want to add guilt on top of trauma.

        1. Rapunzel Rider*

          Obviously OP sounds like a nice person and may be overthinking it but just putting that out there that boss could have additional reaction to it being brought up again. Then again they may also pleased their bully had to face some consequences, who knows?

          1. Dasein9 (he/him)*

            Or pleased that they saved someone from being another victim of their bully.

        2. tango*

          Yeah, this was my thought – if I was the boss this would really stress me out feeling responsible for blowing up someone’s relationship, even if I really justifiably hated the fiance. I might leave it alone for a while and see if the boss warms up, but I think it depends on a lot of factors we can’t know.

    5. Jules the 3rd*

      I agree. But only if LW can actually say that she has ended the relationship, not just the engagement.

      On a personal note: I couldn’t marry someone who’d done that and called it ‘pranks’. They would have to say, “I bullied him, and I am ashamed of it. I’ve done x, y, z to change who I am and try to make amends” with “lots of therapy” being a key thing on the list of things they did. It’s too cruel just to accept and move on.

      1. HonorBox*

        If someone told me that they pulled pranks on a classmate makes me think they hid their jeans after gym class and the classmate had to wear their gym uniform the rest of the day. Or that they took all the lead from their mechanical pencils. Not kind, but also not hugely awful. Pranks don’t include taking and posting photos of someone naked all over school. That’s a crime. So yes, if they’re saying pranks all these years later shows either that they don’t recognize the severity of what they did or are trying to minimize the severity. Neither of those are good options. And while I don’t like being an alarmist, it would make me concerned about what that person is capable of doing going forward.

        1. Reality.Bites*

          At one place I worked, a guy went on his honeymoon and for some reason it was decided to do up his cubicle as a crime scene for when he returned, with a tape outline of a body on the floor.

          I’m okay with pranks like that – one where the victim isn’t meant to be fooled or scared and is immediately “in” on the joke. It’s not my style of humour, but it’s okay.

          1. MK*

            This is probably a “know your audience” type of situation. I do not want to come back from vacation to find my office space a mess and have to fix that before starting work. Also, why is that funny?

            1. Post Malone*

              A coworker covered my desk, monitor, etc in post-it notes while I was on vacation. I was still finding them a couple years after he left, hidden in my desk (that I was leaving behind in an office move). He did know his audience because I found it funny.

            3. Don’t know what to call myself*

              We did this for one of my coworkers who was a huge true crime fan and she thought it was hilarious. It really is a “know your audience” thing.

              In general, when it comes to pranks, I think about something I heard once about boxing. If both parties agree in advance, it’s a boxing match. If they didn’t, it’s assault. I feel something similar about pranks. If you know the person and the situation well enough to know they’ll find it fun, and everybody is happy and comfortable at the end, that’s a prank. Anything else is just bullying.

              1. C*

                Also – if you missed the mark and refuse to apologize, make any sort of amends, or promise not to do that thing again then it’s also just bullying.

              2. Irish Teacher.*

                Yeah, I’m not usually somebody who likes pranks but I would be down for that one.

                My feeling is like yours, that pranks are meant to entertain the person you are pranking, not to humiliate, embarrass, anger or upset them. If you are doing the latter and claim, “it’s a joke; where’s your sense of humour,” that’s bullying.

                But yeah, while I’d expect a situation like this to be one where “pranking” meant bullying, either intentional or just that teens and preteens sometimes don’t exactly know where the line is, I’d still be expecting something like the hiding the jeans or the time one of my classmates hid my Maths book before Maths class. (I think, based on my knowledge of the people involved that they just thought it would be hilarious when I couldn’t find my book and didn’t consider I could get in trouble. The rest of the class had something to say about it, to be fair and it was made clear by some girls I wasn’t even particularly friendly with that it was not cool.) But yeah, those kind of things from teens sort of hover on the line and I wouldn’t hold it against an adult that they did them in their teens. This, on the other hand, is just horrific.

          2. Dahlia*

            I hid 100 tiny plastic ducks to “prank” a friend once. It not only amused her, but other people found it delightful and people were excited about finding a tiny duck for MONTHS.

            1. CeeDoo*

              I had a coworker who was a hunt-and-peck typist. A friend switched up the keys on his keyboard to say HI JAY, but he didn’t realize it because he didn’t know what keys were where. He got very confused for about 10 minutes. That’s a decent prank. He wasn’t running behind on work or anything, so that prank had no damaging effect.

              1. metadata minion*

                This is still a “know your audience” thing, not a “will it interfere with work” thing. I would be furious if someone did that to me, because I have to now spend time fixing my keyboard instead of getting into the groove of work like usual.

                1. Post Malone*

                  I am reminded of that AAM story where an intern was fired for removing their mentor’s shift lock key.

            2. Breadbasket*

              Many years ago I put an official looking “now voice activated!” sign on the break room soda machine on April Fools Day.

              This was a 90s-style soda machine with physical buttons, no credit card reader, cash and coins only. At the time, iPhones were barely invented, tablets didn’t exist, smart voice activated devices just were not a thing people had around or would have had much experience using.

              That did not stop people from trying to say PEPSI loud enough for the machine to hear.

              1. Onomatopoetic*

                Ok, I usually dislike pranks, because there’s usually an element of cruelty, which I don’t like, but that was genuinely funny!

                1. Chocolate Teapot*

                  In the late 80s, early 90s the BBC kids’ show Going Live did an April Fool prank of a new voice activated portable music player. All you had to do was say the name of the artist and the song very clearly, and it would play the tune for you.

              3. Csethiro Ceredin*

                This reminds me of the scene in Star Trek IV where Scotty picks up the mouse from a 1980s computer and says “hellooo… computerrr?”

            3. LL*

              adorable!
              And yes, a work friend once put googly eyes on my phone and computer monitor and maybe somewhere else. It was technically a prank, I guess, but I loved it. And she knew me well enough to know I would love it. I kept the googly eyes up for ages.

          3. Emily Byrd Starr*

            The best prank I ever saw was by the local newspaper on April 1 one year when I was growing up. It was the paper for the town I lived in (Westwood, MA) and the next town over (Dedham, MA). On the front page, it said, “Dedham and Westwood to become one town and the new name will be Dedwood. Story, page 7.”
            On page 7, it said, “APRIL FOOL!”

            Now THAT was a good prank. Funny, clever, harmless, non-offensive, and nothing that will result in anyone panicking.

        2. Emac*

          And the fact that the posting naked pictures, an actual crime, was the *least* of the “pranks” would be a deal breaker for sure.

        3. Judge Judy and Executioner*

          Right? The pranks in my high school were silly and fun, making people laugh together. Even when a staff member’s car was “stolen,” it was quickly found safe and sound on school property, and the staff member thought it was hilarious. Yes, stealing a car is a crime, but the police were never called and no one got hurt physically or emotionally. I would be extremely concerned if someone thought posting naked photos of a classmate was a fun prank.

          1. Worldwalker*

            I wouldn’t want to be involved with someone who had it in them to do something like this.

            I’m actually reminded of something a psych professor said in college: He’d been a psych grad student in the 60s, so he had tried basically every drug known to man. Then he realized that nothing he was taking brought anything into his head that wasn’t there to begin with. Same thing, in a way, with this guy: being positively evil isn’t something that came from outside — it’s something that was in his head to begin with. He is that kind of person.

            He’s the kind of person who found criminal-level cruelty funny when he was younger and now he finds it unimportant. It’s no big deal to him now … just something that happened (without his input, obviously!) back in the day.

            If anything, his dismissal of his prior cruelty as trivial is even worse than him having done it at all.

            1. Miette*

              Yes, this. He can’t fail to realize how after all these years that what he did,objectively, is now viewed as very wrong and psychologically damaging to the victim. Whether or not he realizes it was also a crime, the fact he downplayed it reveals all OP needs to know about his character.

          2. Quill*

            A prank at my high school was that we kept telling freshmen there was a pool concealed under the gym floor.

            Another was cramming a teacher’s desk drawer with origami stars.

            What OP’s fiance did was not a prank, it was a crime.

      2. Elbe*

        Yes! Lots of people have moments they regret, but most people don’t intentionally cause this level of harm. Time passing doesn’t fix a problem of this size. Anyone who had truly changed would be aware of it and able to talk about it in a way that would be reassuring.

    6. bamcheeks*

      It feels very unfair that LW would have to fend off the accusation of being “callous” about the boss’s trauma when she had nothing to do with the bullying and is also going through massive upheavals herself. I am sympathetic to the boss, but as the person in a management position he also has a responsibility to figure out a way to move forward with the management relationship that is fair to LW: she didn’t cause this problem and all the risk shouldn’t be on her side.

      1. Escapee from Corporate Management*

        And that management solution could be to diminish OP’s role or even terminate OP, assuming she is an at will employee. That’s why option 2 is better. If OP is already cutting loose the fiance, she should take positive action to make sure her job is secure.

        1. bamcheeks*

          But there is no guaranteed way to “make sure her job is secure” — it’s about equally possible that the boss would find a direct conversation humiliating or inappropriate, because there is no template for stuff like this. I personally would go with #1 and let the person with the power to fire me decide whether they want to have a direct conversation or not.

          1. MigraineMonth*

            He seems to be trying to avoid her. I would take his cues and not force a confrontation unless it was clear the relationship couldn’t go back to normal on its own.

      2. Happy meal with extra happy*

        I agree with this. I think a lot of people are relating to the boss and thus want the best outcome for him, regardless of whether it’s fair or good for OP.

        1. HonorBox*

          I don’t agree. While many are relating to the boss, I am looking at this through the lens of OP trying to take care of themselves too. If the boss is already (understandably) chilly with OP, it would be good to take some proactive self-preservation steps.

      3. HonorBox*

        While the LW didn’t have anything to do with the actual bullying, they did inadvertently open up a long-standing wound. Not being direct and not accepting that (again inadvertently) they had a hand in opening up that wound might lead the boss to worry that LW isn’t willing to recognize how awful the bullying was.

        I like the suggestion that was made elsewhere in having a conversation with the boss. Offering a thank you to them might seem weird, but thanking the boss for sharing real emotion allowed LW to see who their fiance really is. LW can apologize that sharing the photo put the boss in that spot, of course, too. I think being human and being a little more vulnerable with the boss will show boss who they are… which is a kind and decent person.

        1. bamcheeks*

          might lead the boss to worry that LW isn’t willing to recognize how awful the bullying was

          I realise the boss isn’t the person asking for advice here, but if they were — that’s not an appropriate reaction from the boss. It is absolutely normal and necessary to seek validation for your trauma, but your direct reports are not the people to seek it from.

          LW may have inadvertently triggered the boss, but she’s a bystander: she’s not the person who hurt him. It’s not appropriate to seek validation or recognition from someone you have power over.

          1. Hyaline*

            All of this. Nothing about this past experience ought to impact how the LW is treated as an employee or her job security. The boss would be 100% in the wrong for penalizing, terminating, or in any way affecting her employment. (But because Not All Bosses Are Good, LW may feel the need to tread lightly here.)

          2. Manic Sunday*

            But what did the boss do that was inappropriate? He had an involuntary physical reaction to seeing the photo–a minor one, he just stopped smiling–and asked for confirmation that the man in the photo was OP’s fiancé–as if to be sure he wasn’t misunderstanding the facts. He then took a couple of days off and is now keeping his distance. That is the extent of his actions as far as we know. It doesn’t sound like much time has passed. If it were a month later and boss was still avoiding OP instead of being an engaged manager, that would be concerning, but we have no reason to assume it will happen.

            It occurs to me we shouldn’t assume the boss has any clue the truth has come out between OP and her fiancé. For all he knows, she might not have even noticed or remembered his reaction, much less chosen to raise the issue with her fiancé. The uncertainty as to how much she does or doesn’t know would be enough to cause extreme discomfort for most people.

            The information we have indicates the boss previously had a friendly professional relationship with OP and has tried to behave professionally in awkward circumstances, and if I were in OP’s shoes, I would trust the boss to handle a follow-up conversation with professionalism.

            1. bamcheeks*

              Oh I don’t think he’s done anything appropriate at the moment! But there are various people saying that LW should apologise for her fiancé, that she should show her manager that she recognises the seriousness of the bullying, that she might appear “callous” if she doesn’t address it directly and just tries to re-establish a normal working relationship, that she’s on “thin ground” with her boss— I think a manager who held any of this against her would be inappropriate. But this is all commenter speculation at the moment: the boss in the letter hasn’t done or indicated any intention to do these things.

        2. Wendy Darling*

          The boss didn’t even mention to the LW how awful the bullying was, though. We have no evidence they WANT LW to realize that. Boss had an emotional reaction and then stepped away from the situation.

          LW didn’t find out the severity of the bullying until she went home and questioned her fiance about it.

          IMO if there are professional repercussions from this that’s the boss being inappropriate. I understand the desire to support victims of bullying, I want that too, but that doesn’t mean they get a free pass if they’re crummy to innocent bystanders because of it. Especially not at work.

          1. Smithy*

            Yes…..because let’s say the OP had gone to their fiance and they had simply said that as a high schooler they ended up in a group of “mean boys”, were bullies to a number of people including the OP’s boss, but that growing up they’re now deeply ashamed and have worked towards becoming a better, kinder person in adulthood. The OP could both genuinely believe that response to be the case and to go forward with the wedding.

            In that situation, the OP should neither apologize to the supervisor on behalf of the fiancé nor have to live in fear about what would happen to them at work. It also wouldn’t be remotely appropriate for the OP to try and convince their boss that the fiancé had become a different person.

            While this situation reflects a pretty awful case of bullying – and it sounds like the fiancé never faced consequences during high school. He was also a minor and most importantly, none of this involves the OP’s behavior or decision making.

            It sounds like the way the fiancé behaved when confronted clearly indicated a number of present day behaviors that has given the OP reason to doubt the relationship. But for the OP to apologize for reopening a wound or bringing this back into their supervisor’s life I think could really make things far messier at work.

        3. Beth*

          The boss would have no reason to assume LW knows how awful the bullying was. They didn’t tell OP about it. They just had a weird-vibes reaction to a picture, and OP chose to follow up on that with her fiance.

          I could see the boss wondering if LW knows what their fiance is really like; whether they’re marrying him knowing his history; whether they’re another potential victim getting sucked in. But it would be really weird for him to assume OP definitely knows everything and is either OK with it or refusing to acknowledge it. I think their chilliness is more about feeling awkward around OP due to fear of hearing more about (or even being put in proximity to) his childhood bully.

        4. Jellyfish Catcher*

          I would go with option 2: talk to your boss.
          He was blindsided by the photo, double blindsided by having an employee who now will be married to That Person.
          Without a discussion, it’s natural that he may think you either don’t know what that guy is like, or don’t care or are looking at the money and are still getting married. Or…might tell the world how he was harassed.

          I would say:
          I am very sorry for what happened, I had no idea of his past, but II ended the engagement and all contact.
          You may see me as a painful reminder right now, I understand.
          But I see you as the person who saved me, from the same fate.

          I’m grateful, I’m lucky and have no need to mention your past, or mine.
          I can only thank you.

        5. metadata minion*

          Since the boss wasn’t the one who disclosed what actually happened, he still doesn’t know that the LW knows anything.

        6. C*

          Boss seems to have been pretty careful not to say anything to LW about what sort of person Ex is. As far as Boss might know, LW might still not know what happened in high school – LW might never have gotten any sort of answer from Ex, or even realized they should ask at all.

      4. hbc*

        I dunno–I’m not sure there’s a good option that’s fair to everyone here. As the victim of actual crimes and abuse, I think it’s reasonable for the boss to want to keep their “people I see every week” circle more than one degree of separation away from their abuser. And if the boss comes in to resign over this, the grandboss might well decide that OP is more easily replaced or moved elsewhere.

        I think it’s better for OP to get out in front of this (maybe with an email if face-to-face is fraught) then to just hope that the boss’s dread of the upcoming family picnic won’t affect their standing.

    7. ICodeForFood*

      As someone who was relentlessly bullied from elementary thorugh high school, I agree that #2 is the best option.

      1. RunShaker*

        I am in agreement option# 2 is best. Even if OP says “I’m evaluating our relationship” and that OP wants to ensure they have good relationship with boss. The OP doesn’t have to tell her boss “we’re breaking up.” As someone that was bullied in grade school and thinking about the previous letters on bullies that came in, is another reason why I think option 2 is best.

      2. Resident Catholicville, U.S.A.*

        I don’t know- as someone who was bullied extensively in my youth, I don’t know if I’d want to address it this far out from the bullying. I’ve worked very hard to move on past that part of my life. Not only do I not want to talk about my past trauma, I don’t want to be put in the position where I have to make someone else feel better about the steps they’re taking to reconcile that, either because they’re the person who did the bullying or they’re related in some way to the bullier. I’m not saying I’d prefer everything to be aggressively normal- I’d probably want some distance from the person for awhile (stay cordial, polite, do work related issues, very little personal interaction) until I’d have time to process everything.

        I’m in my 40’s, so most of this happened long enough ago that I’ve moved on, but if I found someone I worked with was related to or married to one of my bullies, I’d probably fall on the side of, “This just needs to be a cordial work relationship and not move beyond it.” Having a big to-do about it is probably going to be more awkward than anything else, especially since I can’t hold someone else accountable for the bullying party’s actions.

        1. Smithy*

          Yeah….I will also add that the most awful things that happened to me via bullying as a child – and nothing as bad as having naked pictures spread – hearing that someone from my adult life now knows all about it would be retraumatizing.

    8. Successful Birthday Rememberer*

      I completely agree – it’s obvioulsy already a problem. It will be safer for her job to say something right away.

      1. NothingIsLittle*

        I disagree that it’s “obviously already a problem.” Boss is currently just avoiding the OP during what is presumably less than a week out from learning that her fiancé is someone who wronged him horribly. I think it’s very reasonable to give the boss a week or two to gain distance and then reassess.

        I was bullied throughout my schooling (though not close to as badly as this situation). I would be pretty alarmed to meet anyone associated with the people who bullied me, but I also would want to move on and not have to justify my ability to view them as a separate entity from the person who made my life hell.

    9. Productivity Pigeon*

      I agree.

      To find out something like this and then ignoring it, especially if OP ends up breaking the engagement, seems minimizing to me.

      OP doesn’t need to apologize for having fallen in love with this guy or anything but to say nothing and refusing to acknowledge it doesn’t feel right.

      (If it turns out this is real.)

    10. Hyaline*

      I think whether “pretend things are normal” comes off as callous or in fact very considerate depends entirely on the boss’s temperament and preferences, which are hard to know in a workplace setting. Some people prefer airing everything and talking it out, some people would find that invasive and intrusive and would far prefer “aggressively normal,” taking “pretend things are ok” as a kindness to protect them. I think the best option is to be prepared to do either, and read the room with the boss.

      1. Ellis Bell*

        Yeah you would have to take the temperature for this one on the ground. If the boss is signalling that they’d really rather not talk about it, OP will pick that up better than we can. If on the other hand you can cut the tension with a knife, and the instincts are screaming at you to clear the air, OP will also know when/if there is a good time to say explicitly something. I honestly think OP can’t go wrong here. They have taken this news so seriously they’ve ended the engagement; I don’t see how the boss will fail to pick up on that.

        2. Boof*

          And if they do talk about it, OP will have to be careful to keep it brief and not expect any specific reaction from their boss, just communicate “hey I had no idea and it’s making me seriously reevaluate things, I think you’re a great boss and wanted to let you know I appreciate you” and that’s it.

      2. MigraineMonth*

        From the fact that the boss is currently *avoiding* OP, I think he wants to avoid any kind of conversation with her about the bullying. I think acting as if you don’t know details about your boss’ adolescent trauma is probably the best move, at least to start with.

        If the relationship gets more strained, or if the boss retaliates in any way, address the elephant then. Until then, it seems best to let the boss take the lead in how much he wants to disclose (which seems like none at all).

    11. sometimeswhy*

      Another ditto amongst the dittos. I have cut off close friends off for “I never saw them do the bad things” nonsense about people who did significant harm to me or people I love. Once, an entire friend group for sheltering the abusers, plural. The period after drawing my line in the sand was lonely but I have not regretted it, not even a little.

      If I were this person’s supervisor, I would appreciate some sort of reassurance. The reassurance doesn’t even need to be a conversation, it can be Alison’s statement prefaced with, “This is uncomfortable and I don’t need to have a back and forth about it but I want to let you know…” and then leave. Let them follow up if they want but don’t expect it. Say your bit and THEN act normal.

      Without that follow up, I would either need to overlay some really formal guardrails on how we interacted to check myself against holding it against her or work with HR to move me out of her reporting structure. This isn’t theoretical for me. I have an analogous situation at work and we’re strictly and forever out of each other’s reporting lines if she ever.

    12. CJ*

      One more for this pile. While there’s some value of “go along to get along”, there’s also a lot of value in having a bright pink “I’m not with stupid” shirt. Acknowledge the harm to the (boss) person, and show by actions that it will not happen again.

    13. ExCon(sultant)*

      I worry that the naked pictures are going to make option 2 more difficult. The boss probably doesn’t want his report thinking of him naked, and is probably terrified that, with her knowing what happened, word of it could get out at the office. If it had been fully-clothed bullying, I think it would be easier to talk about now.

    14. NothingIsLittle*

      Boss wasn’t the person who told her about the bullying, though, it was Fiancé. Boss could very reasonably assume that OP has no idea about the behavior; I doubt it would seem callous unless there are details we’re missing.

    15. Coffee Protein Drink*

      I agree. Acting like everything is normal diminishes what happened to the boss. Yes, it was a long time ago, but bullying leaves scars, especially at this level.

    16. MCMonkeybean*

      I do too, especially since if she told all her coworkers about the wedding and was going to invite them she’d have to tell them it was canceled anyway. There’s already going to be lots of awkward conversations about it, might as well also take the extra time and awkwardness to make sure her boss knows she would never support that kind of behavior.

      You definitely have to pick your words carefully and you don’t want to leave your boss feeling like “oh no I broke up my employees relationship.” I think Alison’s script navigates it pretty well.

    17. HB*

      A crime, really. If this letter is true, she needs to dump this guy yesterday. People with such a deep cruel streak don’t really change.

    18. Silver Robin*

      I am not sure…trying to game it out in my head:
      1) LW is aggressively normal, engagement stands: absolutely callous

      2) LW is aggressively normal, relationship quietly ended: probably callous

      3) LW is aggressively normal, relationship publicly ended: maybe fine? Lets the boss decide how much of this to talk about or not? But also leaves things potentially unresolved until the normal just overwhelms it?

      4) LW talks to boss: would have to be handled really gently and depends a lot on the relationship they have. But since LW already wanted to invite Boss…maybe something like “I am just updating folks that the engagement/relationship is over and I also wanted to apologize for bringing up painful memories. I learned from him how truly awful he was to you and it completely changed my feelings towards him.” Extremely unsure about whether to make it explicit that the reason for this is the bullying/ex’s current attitude towards it. Because the problem now is that LW knows some awful, humiliating stories from Boss’s childhood from another party (from the bully!). And it is very reasonably that Boss might not want to talk about this with anyone and is now upset that anyone from their adult life knows.

      1. Silver Robin*

        note: the “callous” is assuming some amount of closeness with the boss. Basing that on the fact that boss is invited. If I had a clearly emotional reaction to something my friend brought up and they were just cheerfully normal afterwards, it would be…weird. Considering that this is a heavy topic for Boss too, it might just pile onto the weird in a negative way. Ugh, this is so sticky and awful (for everyone except the fiance, well deserved loss on his part).

      2. Smithy*

        With us knowing all of the details – I get how #1 seems entirely callous. However, had the OP’s fiancé come clean immediately that as a teen they’d engage in horrific bullying, they’d realized as they’d gotten older how awful it was, deeply repent the behavior and have committed to living an adult life that is kinder and more compassionate – #1 isn’t really fair.

        And as the boss hasn’t necessarily read this letter, as their supervisor, they really do have to give the OP the benefit of the doubt. That this isn’t a situation they know about, and also that the bully has changed.

        I do think the point of being aggressively normal is that it’s not putting the pressure on the boss to give forgiveness.

        1. Jellyfish Catcher*

          The LW should clear the air with her boss – because she’s the only one who can.
          The boss has no idea if the LW/employee knows what her ex or might even gossip about it.
          It’s clearly negatively affecting their working relationship, and only she can fix it.

          It doesn’t have to be a deep discussion.
          “Boss, I have cancelled my wedding. I very recently learned of some very negative behavior of him, years ago, enough to know that he is not for me.
          I don’t know the details, don’t need to, nor will I discuss this with others.

          It was an awful coincidence, I had no idea. But it saved me from a miserable marriage. I am grateful for that, and hope that we can both return to a successful working relationship and never think of this again.

    19. PinkUnicornClub*

      Yes, this is a rare instance where I disagree with Alison on that very specific aspect. Based on the fact that the boss was so taken aback they had to take two days off, this goes far beyond normal dynamics and high school teasing. There’s very serious trauma there (and posting nude photos that were taken by force NOT being the worst thing they did is very, very troubling).

      Acting aggressively normal could signal socially to the boss that you’re not taking their feelings seriously, and lead to a lack of trust. While normally, as the person in power, it’s your boss’s responsibility to be the level head, the amount of trauma this person likely has from the finance’s treatment creates a totally different scenario. I’d want to reassure them that I took their experience very seriously, which I think requires direct communication in this instance.

      1. MigraineMonth*

        I’d definitely agree if *the boss* had shared what happened to them. The boss didn’t share what happened to them and doesn’t know that LW knows.

        I would be horrified if someone at work brought up the fact that I was the victim of a sex crime, *even if* they did so in order to tell me they supported me. He should have had the choice of who to disclose that to, and he did not choose to disclose to OP.

        1. Baunilha*

          I think we are the minority here, MigraineMonth, but I agree with you. Boss didn’t share anything — all he did was take a few days off and stay politely away from OP. For all we know, the time off could be totally unrelated, and boss may be thinking he did a good job hiding his feelings from the OP. He doesn’t know that she knows.
          I would not bring up the prank. Alison is right: just make a point of being aggressively normal and discreetly share the news of the break up. Maybe boss will do the math.

          Also, as someone who was bullied in school, I wouldn’t want someone bringing it up again, especially someone who I never talked about it with. Just because I’ve moved on from it doesn’t mean I want to rehash it all over again.

    20. nnn*

      Why would acting normal seem callous when the boss doesn’t even know that the LW knows what happened? Boss probably assumes LW has no idea.

    21. Manic Sunday*

      I agree, and I would act on option 2 sooner instead of later. The worst case scenario, if OP waits quietly for things to go back to normal, is that the time spent waiting will be more than enough time for their boss’s feelings to fester and their workplace relationship to deteriorate. If OP acts now, as long as they approach it with compassion and professionalism, what’s the worst that is likely to happen given what we know about the boss? That it’ll be a super uncomfortable conversation? That boss won’t take OP at their word? Things are already uncomfortable, and boss may already be questioning his former good opinion of OP. I would not want to risk letting this go on any longer than it has to.

      Also, OP describes a boss who has been friendly towards them and shown an interest in their life. Maybe if their work relationship had previously been cool and distant, or if there had been existing tensions between them, option 1 would be more appropriate.

    22. Beth*

      I don’t agree. In the boss’s shoes, I’d like to know the engagement isn’t moving forward–it would be great to know that I wouldn’t run into my bully at the office holiday party, and it would go a long way toward resolving any niggling doubts that this might have raised about OP’s judgement or character.

      But I would absolutely not want a big conversation about it with OP. I don’t want to talk about my childhood traumas at work! I don’t need apologies from someone who wasn’t involved in the trauma. I don’t want to feel responsible–even indirectly–for someone’s engagement falling apart. That’s a lot, it’s very feelings-heavy, it’s not a thing I need to be dealing with at work.

      I’d prefer to just hear through the grapevine that OP’s wedding is off, they broke up, OP is moving out on her own, etc. In OP’s shoes, I’d make sure to mention those big life changes to the office gossip, and trust that word will get around. The boss can raise the topic himself if he wants to talk more about it.

      1. Manic Sunday*

        You make some good points, and I wonder whether there’s a middle ground that would simultaneously clear up any misconceptions on the boss’s part which could be harmful to OP’s standing at work, relieve the boss’s feelings, and mitigate the risk of further awkwardness.

        If OP is comfortable saying a little more than she needs to at work, she could tell the grapevine she chose to end her engagement because it turns out her fiancé wasn’t the person she thought, he lacks integrity, she has serious concerns about his character, or some vague wording like that. This would have the added benefit of heading off unnecessary pity due to incorrect assumptions that she was dumped or had her heart broken. If she can give the impression of being glad to have dodged a bullet, then no one needs to throw anyone a pity party.

    23. Blue Pen*

      Yeah, same. I don’t think you have to go into specifics—especially what your boss went through—but I think they should know and would appreciate knowing. It says a lot about you.

    24. Laura*

      I agree! I think doing it gently so as to not “corner” the boss is a good idea. But otherwise, it might be useful information for your boss about *your* character on how you feel about the trauma their hopefully now ex-fiance inflicted.

    25. RagingADHD*

      It might also seem like LW is respecting the boss’ privacy and agency, since the boss did not choose to tell LW why they reacted the way they did, and has also chosen (so far) not to bring it up.

      It is a delicate situation all around, and any action or inaction by the LW could be the wrong one (or the right one). That’s why it’s best for the LW, as the person who actually knows the boss IRL, to try to make a determination about how the boss might receive their response based on a) their direct knowledge of the boss’ personality, and b) the boss’ demeanor when they return from PTO.

  3. JP*

    I think #1 is best. Boss will learn soon enough that you’ve called off the engagement, and it spares them an awkward/embarrassing conversation about something that they probably would rather leave in the past.

    1. Reality.Bites*

      How about a compromise where boss will figure out what happened without having to confront his trauma again in discussion?

      Do Option one, but immediately send out your “Unsave-the-dates”

      1. Carol the happy*

        You would need to make sure to tell it so the boss doesn’t feel guilty- it’s odd how victimized people can feel guilty for exposing a filthy crime.

    2. RIP Pillowfort*

      I’d say it’s the safer option without knowing how well the boss has processed his trauma.

      I went through some really criminal things done to me by people in school. Enough that I have a lot of feelings about how safe my child is in a school with their peers. I’m healed enough to know that I’m being driven by my own issues and that my experience isn’t going to be hers. But it doesn’t always stop me from having really strong reactions from triggers.

      I’d probably let the office as a whole know that the wedding is off and go forward from there to see if the avoidance continues before trying to engage in a stronger discussion. I just really hope the boss doesn’t completely ice out the OP because of something they had no idea about.

    3. LSM*

      I agree, and I’m surprised a number of people seem to be so in favor of option 2. To me, the boss has clearly signaled they do not want to talk about this. I would respect that. Presumably, the OP will start spreading the word that the engagement was called off. I’d probably let that circulate around through the office rumor mill rather than making a big deal about it.

      Now, if the boss had opened up to OP about the bullying, then I would go with option 2. But since that didn’t happen, I think OP should follow boss’s lead.

      I didn’t go through bullying, but I suffered severe forms of trauma/abuse in childhood. If someone I worked with found out about my history from someone else, I would hope they would treat me exactly how they did before. If I want to discuss my trauma with someone, I’ll bring it up in my own time and when I’m ready.

  4. Not Me*

    Yeah, this letter does seem like soap- opera fiction.
    But, taking it at face – value —
    could I add an option 3-
    Tell or write your boss that you thank God for putting him in your life, because, without him you would have *never known* this about your (former) fiance. and express your thanks.

    2. CityMouse*

      I agree with all points and I feel like I’ve read something similar before.

      But, if this is true, yes Alison is correct. Tell boss you appreciate the context.

    3. juliebulie*

      Actually – I like this even better than option 2. Or maybe as an add-on to 2.
      Whether it’s 2 or 3, it can be a letter. Then the boss does not have to visibly react.

    4. juliebulie*

      And as for the letter’s plausibility – I find it quite plausible. (As long as OP doesn’t update us in a few months and say she married the boss instead. I hate romcoms!!)

      1. EvilQueenRegina*

        If it really was a romcom plot, that’s probably pretty much how it would go down.

      2. ecnaseener*

        I also find it plausible, mainly because if I were writing a fake letter, I wouldn’t say I had already pretty much decided I couldn’t marry him. I’d leave that piece wide open for more drama.

      3. Myrin*

        Yeah, I found it really interesting that this pinged Alison’s alarm bells, mainly because nothing in it seems particularly fantastical to me.
        If the CEBro letter was real – which we can basically be certain it was, especially with that OP’s update -, I don’t see why this actually much more mundane situation shouldn’t be. (Not a criticism of Alison’s in any way! She might well be right! I really do mean that it’s interesting to me what makes different people have different reaction to the same thing.)

        1. Your Former Password Resetter*

          I think the recent increase in trolling is part of that. Those people probably like to send in fake drama-bait letters too.

          Either way, Allison’s advice is usually widely applicable and easy to modify, so it’s still good to answer these letters.

          1. Strive to Excel*

            Just the three linked letters demonstrate that there’s plenty of people out there with a conflict between their personal and professional lives in unexpected ways. I also recall an older letter written by the bully; the company they were applying to had a rockstar employee who was their prior target. They ended up spiraling pretty hard.

            I like Alison’s approach of “maybe this is fake, but the advice could be useful so I’m going to write it up anyways”.

            1. Marion Ravenwood*

              That’s the one linked to as ‘didn’t get the job because I was a bully in high school’.

              I hope that OP took some time to reflect on themselves and made some changes since the update, and that they’re doing better now.

        3. T.N.H*

          The part about her parents wanting her to marry him because he’s rich and treats her well is the alarm bells for me. I’ve never heard this in real life, only on Reddit. Also, if he’s “you don’t have to work anymore” rich then she shouldn’t care whether her relationship with her boss has suffered. If he just has a good job, then he’s not rich enough for her parents to be invested.

          1. juliebulie*

            I have aunts who talk that way. I mean the “he’s rich and he’s good to you.”

        4. SnackAttack*

          It reads just like an AI thread someone would post on Reddit. It could be legit, but as someone who reads AITA a lot, it checks all the boxes of a fake AI post.

    5. NothingIsLittle*

      As someone who was bullied (though not nearly as badly as this situation) that would make me wildly uncomfortable. I don’t want to be thanked for being horribly wronged by someone. I understand that your intention is not to suggest that Boss being terrorized by the fiancé was a good thing, but for someone dealing with recently revived trauma it’s too easily read that way.

      1. Not me*

        Nothing is Little..
        Thanks for the heads up…
        I guess I should be crystal clear to my boss that my thanks is for him being willing to tell me about what must be a very traumatising situation.
        (and of course expressing my sympathy for his going through that)

        I would certainly not want to appear/ be dismissive of Boss’ hurt..

        1. Seeking Second Childhood*

          Boss did not tell LW about the bullying. She got that out of her ex.

    6. Palmer*

      Never known until it was too late.

      If someone is a sociopath, I want to know as soon as possible. Cut the tumor out before it moves in and you have a mortgage and a kid.

    7. MrsThePlague*

      So interesting that people think this might not be legit. Literally nothing about it seems unusual to me:
      -people write in all the time about running into exes and former friends, etc., in the workplace – even really toxic, terrible exes, etc – due to living in a small town.

      -The part about the parents wanting her to stay with him because he’s wealthy and treats her well – also pretty common in advice columns, and definitely in real life.

      -And from the reaction of most people here, it seems clear that many people who found themselves in this kind of situation would break up with the person it involved.

      What’s the unbelievable part?

      If it was like: “and then it turned out my boss was actually a prince from a tiny European country!” I’d be like, okay, that’s a stretch. But this feels like a very plausible variation of lots of letters I’ve read here and in other advice columns. If we think this is fake, then 95% of the letters sent in probably are, too!

      Either way, I much prefer Allison’s stance on just assuming truthfulness in writers. It’s tiresome and distracting debating the fake or not fake question, you don’t win anything for guessing correctly, and we’ll never know one way or another. It’s much more helpful and interesting just working the problem as presented.

  5. Amber Rose*

    So, not pranks, but crimes. He wasn’t a prankster he was a criminal.

    If you frame it that way, I think people will understand. “My fiancé hid that he used to commit crimes” is a pretty straightforward reason to break off an engagement, and not one to be humiliated by either.

    1. Presea*

      Hid it, and also minimized it when it came to light. And the crimes were cruel ones that traumatized people, not ones that are of little moral weight like cannabis use.

    2. JustCuz*

      He used to commit crimes *against* others that caused long term, significant harm. That’s what he did and that’s what LW should say.

    4. Three Flowers*

      Yes. We are talking about a sexual crime against a minor—ie, child porn. OP, your fiancé committed a sexual crime against a minor. Don’t let yourself evade that.

  6. Athenae*

    “He’s rich and treats me well.” Sure he does. NOW. He won’t eventually.

    A bully’s a bully. If he truly wanted to show he’d reformed he’d ask her to take an apology, a REAL one, not a “sorry if you were bummed” note, letter to the boss offering regret for past actions and a desire for forgiveness. But he’s trying to make it up with the fiancee, not reform himself as a person.

    1. MsM*

      If I were the boss, I don’t think I’d want to hear from the guy, even for an apology. I certainly wouldn’t be impressed or mollified by a secondhand message.

      1. HonorBox*

        Agreed. LW can apologize for their actions causing a painful wound to be opened up. That’ll be awkward enough. But I’m sure boss will appreciate hearing that, because it shows the maturity that the fiance doesn’t have. I can’t imagine hearing a second-hand apology for that kind of trauma. Not only would it land poorly, the boss might have thoughts about the LW and how they’re allowing the fiance to skate.

        1. NothingIsLittle*

          Do not be sure the boss would appreciate that. Why are you apologizing? If you’re telling him that you don’t support that behavior, you communicate that by ending the relationship; that’s something an “unsave the date” would tell him. If you’re telling him you didn’t realize your fiancé would bring up bad feelings… obviously you didn’t? The boss chose not to explain how he recognized the fiancé, I suspect that means he’d rather not have to justify that he doesn’t judge OP by the hopefully ex-fiance’s actions.

          I’m sure there are people that would find a conversation valuable! But equally, there are people who would feel like you were apologizing to make yourself feel better at their expense by revisiting an issue they consider closed.

    2. Double A*

      I do believe people can change and grow. But what that looks like on the other side is accepting responsibility and accountability. How the fiance reacted is… not that.

    3. Ellis Bell*

      All humans should treat each other well; it’s the lowest of bars. But people are never really referring to that when they say this. There is a segment of the population who only ever uses this phrase to discuss women settling in relationships and it’s said in a tone of voice that implies said woman is a tamagotchi who needs to be looked after. Apologies if I’m misgendering OP, but the “he’s rich” also added to this tone for me.

    4. Slow Gin Lizz*

      Yeah, he treats you well now because he still hasn’t sealed the deal yet. Once you’re actually married and leaving him is a lot harder, will he continue to treat you well?

      And also, the cynic in me feels the need to ask: does he actually treat you well, though? Or is that just what your parents know about how he treats you? Is he one of those people who on the surface seems like he treats you well but there is an undercurrent of emotional abuse that is hard to put your finger on? A recent Captain Awkward letter addressed a situation where the LW was upset that her sister shouted at sister’s partner when he was making fun of her and the LW thought it was uncalled for but CA read into the situation and thought that maybe Partner was causing a lot of stress that LW didn’t see and so it only seemed to LW that sister was overreacting but maybe she wasn’t (and was being gaslit by Partner). I’ll link to the letter in a sec. It might be just AAM Fanfic that I’m writing here, but it could very well be that if you look back at how your fiance has acted since you’ve known him, you might discover that he might not actually be all that great of a person now. (Sounds to me like he isn’t.)

      Anyway, this sure is tough. I hope you figure the situation out soon, LW. I’m sure you’ll be paying more attention to how your fiance acts in the coming weeks and months and that’ll be helpful in figuring out what you want to do. Good luck.

        1. Marion Ravenwood*

          Oh man, as someone who’s been in Shouty Sister’s position (albeit with other relatives rather than a partner), that one really hit home.

  7. My Boss is Dumber than Yours*

    “I’m disgusted that the man I love and want to spend the rest of my life with could ever be this person.”

    This isn’t the man you love and want to spend the rest of your life with. You’re mourning the fact that your fiancé is a bully (and probably worse), and because of that you realized that the Venn Diagram of him and “person you want to be with” no longer overlaps. This is incredibly difficult, but reframing this statement is one of many steps. Good luck leaving this guy.

    1. My Boss is Dumber than Yours*

      Oh, and on a more personal note, my wife’s sister is married to a guy who we all watched be a verbal and physical bully into his late 20s. She still married him, with her parents’ and other siblings’ blessings, because he was wealthy, bought her nice things, came from a good background, etc. Now, he never takes the kids to school and made it such that either she had to quit her job or enlist her parents to drive them. And about every other family gathering she has some mysterious facial injury from her definitely-real-recreational-softball league…

      1. Not Tom, Just Petty*

        I think this is why Alison risked posting a questionable letter. Ken Kesey opened “One Flew Over the Cuckoo’s Nest” with the statement: “It may not have happened, but it’s true.”

        1. My Boss is Dumber than Yours*

          Oh, they don’t think they’re going through anything, unfortunately. My in laws are all just upset that my wife married a Jewish guy whose parents/grandparents were working class… they (including SIL herself) still think my SIL’s marriage is peachy…

          1. Not Tom, Just Petty*

            So, not Ken Kesey, but a Philip Roth vignette. Live well, friend commenter and friend commenter’s wife.

    2. Dust Bunny*

      Seconding this. You’re mourning the loss of the person you thought he was and the marriage you thought you’d have. Please enlist a therapist if you think a third party who is not dazzled by his money would help you untangle this.

    3. Emily Byrd Starr*

      “you realized that the Venn Diagram of him and “person you want to be with” no longer overlaps.”

      I really like that way of expressing it! I think it can apply to so many ex-relationships.

  8. Aggretsuko*

    I suspect a lot of the boss issue will go away once you say “we broke up, and thank you because otherwise I would never have known he’s such a glass bowl.”

      1. Mark Knopfler’s Headband*

        Rhyming slang for a very unpleasant person. It’s often used in advice columns (which as Carolyn Hax at the Washington Post) and among their commenters.

  9. Snarkus Aurelius*

    None of this is your fault. I understand the urge to be embarrassed because of your choice, but don’t go to that dark place. If anything, your boss did you a weird favor.

    That said, I’m really, really proud of you for calling off the engagement. Not a lot of people would have the courage to do it, including your parents. That’s a very, very admirable thing.

    As for your boss, a direct conversation would be best. Acting like nothing happened doesn’t demonstrate where *you* stand in all of this. Your boss needs to know that.

    And as for everyone who thinks youthful mistakes shouldn’t be held against this person…

    1) what this man did was illegal and went was beyond juvenile pranks. This is straight up trauma.

    2) children as young as toddlers know the difference between right and wrong so this guy did know what he was doing was wrong. What’s worse is that he was closer to being an adult than a child when he did all of it.

    3) in all that time, there was nothing in this man’s conscience or brain that ever told him to stop terrorizing another human being. The only reason he did is because they graduated.

    4) his reaction was… everything, I’m afraid. He’s sorry he got caught not that he did it.

    I can’t wait for my reunion this year! I’m gonna have a couple of polite conversations that go over these points.

    1. Observer*

      4) his reaction was… everything, I’m afraid. He’s sorry he got caught not that he did it.

      I think that this is the most salient point. People can change. But the first step is to *acknowledge* the badness of what you did. Which this guy is not doing.

      1. Catherine UK*

        Yep, if he had changed he would’ve been very ashamed and remorseful about what he had done, and would probably be offering to apologise directly to the boss now. Presumably he would’ve already told his fiancee earlier in the relationship (and probably a therapist as mentioned by someone above) how bad a person he used to be and how ashamed he is now.

    3. NothingIsLittle*

      Presuming this is real, OP has not yet called off the engagement.
      Paragraph 7, “My engagement is almost over.” (emphasis is mine)

      1. NothingIsLittle*

        I should have said, “Presuming this is real as written.” It could be that it has been called off and the claim that it hasn’t is meant to be anonymizing.

      2. londonedit*

        I took that to mean ‘we’re about to get married’ (as in, the engagement is almost over because the wedding is rapidly approaching) rather than ‘I am about to break up with him’. It would be a weird way to phrase the latter (though the letter is full of slightly odd phrasing, which might have been part of what pinged Alison’s alarm bells).

        Still, the OP does say they can’t be with Fiance now they know this about him, so we can assume they have split up.

    4. JB*

      As an adult he still doesn’t recognise or tried to avoid acknowledging the severity of his actions. He first tried to avoid addressing the topic, then was very careful about his wording with no hint of remorse as to limit his culpability.

      He’s shown his true colours, as have OP’s parents.

      When OP does talk to her boss, she needs to convey that she’s not blaming or judging him whatsoever. She needs as many people by her side as she can get especially as she’s not getting it from family and very unlikely to from her friend group.

  10. But Of Course*

    Honestly, I’d probably have a similar in-the-moment reaction to someone announcing their engagement to one of my bullies (unsurprisingly, not the one who apologized for his treatment of me). The question would be whether she knew and agreed with him, whether she believed he’d changed and was going to try to convince me of that, whether he HAD changed – basically, does my employee act like my bully is right?

    So I lean to option 2, followed by option 1 to give the relationship time to recover from this.

  11. Keymaster of Gozer (she/her)*

    I had a think about how Id react if one of my staff announced their engagement to the bully at school who put me in the hospital several times. Probably exactly how your boss did – get some time away and distance to recalibrate and reassure my mind and deal with the possible flashbacks of that time.

    As to what would make me feel better in a professional environment after – asking me for a quiet meeting, make it clear it’s informal and off the record and that it is an I’m so sorry, I had no idea discussion.

    I wouldn’t be happy hearing you’d broken up because of it because I’d be afraid you’re going to turn hostile against me down the road for wrecking your marriage. Saying you’re considering matters after finding out this new information though would be fine and elevate you in my estimation regardless of your ultimate decision.

    After that? Dont bring the subject up again.

    I cannot speak as to your relationship as I’ve had experience of being very badly bullied and I dont believe that person has ever changed, but Ive also behaved very badly in my past and work actively to make sure I never do it again. I will say to decide for yourself, write it all down if it helps.

    1. Ellis Bell*

      “I wouldn’t be happy hearing you’d broken up because of it because I’d be afraid you’re going to turn hostile against me down the road for wrecking your marriage.” I actually don’t know how you would get to this conclusion. I’ve had a marriage “wrecked” by finding out the truth of what I was getting into…and all I was was grateful to the person for saving me. I think that’s an odd conclusion. Sure, some people go into denial of what’s happening, but those people usually stay.

      1. Boof*

        I think it’s too easy to start second guessing and feeling guilty about things – so it’s probably best LW not bring up “ending the engagement” if it comes to that unless somehow that comes up more organically – like if the boss asks about the wedding plans or something. “oh it wasn’t working out, better luck next time!” or something IDK.

      2. Targ*

        “Shooting the messenger” is a very real phenomenon….. evidenced by the fact that we have a name for it.

          1. Jules the 3rd*

            Yes and even when it’s just bad news.

            For example, I know someone who got mad at me for telling her that her boyfriend had just hit on me. Not my fault, and it was an immediate no, but she did indeed get mad at me for spoiling her relationship. It’s a valid concern, but that’s where ‘aggressively normal’ comes in.

      3. Keymaster of Gozer (She/Her)*

        That’s how my mind would work! And I very much understand the illogical nature of its operation at times. To be fair, it’s a highly non standard operating system.

    2. Boof*

      Thank you, for sharing; I think this is perfect advise too – be careful not to make the conversation about yourself and the impact on you, LW, but it’s ok to let boss privately and discretely know you had no idea about your fiance’s past and you’re taking it seriously. Then never speak of it again.

    3. NothingIsLittle*

      It’s so interesting to hear this, because it’s the opposite of my reactions! I would have trouble believing someone didn’t condone the fiancé’s behavior if the relationship survived, and I would feel like needing a conversation to tell me about it meant you didn’t trust me to view you as a separate entity from the fiancé. I don’t want to have to think about those people again, and I especially do not want to have to justify my reactions to that past.

      Most of my bullying wasn’t physical, though, and it was mostly girls, so those may contribute to the different preferences.

    4. Likewise*

      For what it’s worth, Keymaster, I would have the same reactions as you. My bullying and abuse were also very physical so perhaps that has something to do with it. People shoot the messenger in all sorts of circumstances. In any case, you don’t owe anyone an explanation of your reaction – no matter how self-righteous some commenters are.

  12. Jules the 3rd*

    LW: Think hard about how your fiancé treats people now. Is he polite to wait staff / tech support / grocery clerks / drivers, or brusque? Does he complain about ‘lazy’ workers?

    I’ll bet $20 that he’s brusque, even rude. Use this to refine your criteria for picking significant partners. If you really want someone who’s never been a bully, look for someone who’s polite when purchasing services.

    1. Ellis Bell*

      Not necessarily! Had some experience here. Everything is sunshine and roses when the Mark is present.

        1. Ellis Bell*

          True. Now, the mask is off I think there will definitely be some stand out moments in OP’s memory; no matter how good his act was, it’s never quite the same as the genuine thing.

          1. Jules the 3rd*

            TRUTH. It’s never quite the same, and once you see it, you notice it in future.

      2. DeeJay*

        Yes, the advice “Don’t look at how they treat you on the date, look at how they treat the waiter” is now so well-known it’s been suggested that if your date treats the waiter badly it may well be they want to end things with you but can’t bring themselves to say so. So instead they behave badly in the hope that you’ll dump them.

        And how many times have abuse victims not been believed because the abuser put on a kindly mask to everyone else?

    2. Georgia Carolyn Mason*

      I was about 16 when an older friend taught me to watch out for someone who’s “nice to you but mean to the waitress.” It’s been a reliable red flag several times!

    1. AnReAr*

      I’m getting modern KDrama from it. Apparently there’s a new spate of English language online only soap operas that advertise on TikTok, and I recognize a lot of the plot beats in the ads and clips from the few KDramas I’ve read. It’s pretty much all either office romance stuff but involving high level bosses or straight up rich people marrying for contract negotiations so still business related.

      Still, as Alison said reality can be stranger than fiction. My family has stories that nobody outside would ever believe, and the most unbelievable true one does sound like a cheesey edgy 90s romcom.

      1. Snarkus Aurelius*

        The Glory was very, very hard to watch, but the ending was very, very satisfying. Unfortunately, the bullying incidents on the show are based on real life events.

      2. Nebula*

        I was telling a story about my past to someone last night and they were gobsmacked and said it sounded like something out of a soap opera. Since it’s just part of my life, I’ve never really thought of it like that, but even while I was telling the story and seeing their reaction I was like “Oh this was actually quite dramatic, wasn’t it.”

        This story definitely does read like something off Reddit – it’s less that it’s wildly unrealistic, more that it hits a lot of the same beats that lots of those stories do – but at the end of the day, it definitely could be a real situation, and maybe it will help someone who is actually going through something similar, if it is fake.

  14. HonorBox*

    LW, I’m really sorry. I think you’re doing the right thing by not staying with this guy. I agree that many people are very different now than they were as teens, but your fiance’s reaction doesn’t lead me to think he’s changed as much as you’d hope he would have.

    I think 2, while potentially very uncomfortable, is probably the better way to go here. The LW didn’t do anything wrong, but the boss was clearly upset when they saw the photo of the fiance. The LW doesn’t really owe the boss an apology, but this might be a circumstance in which apologizing for doing something that inadvertently and unintentionally brought up past emotions and circumstances could be helpful. LW can explain what they’ve learned, and telling the boss directly that they’ve ended the engagement may again not be necessary, but might be helpful both for the boss and the ongoing relationship between boss and LW.

  15. On A Break*

    I am also very much on the “even if it’s a fake story it can tell us a lot and we can talk about how to actually react in this situation”. It’s my reaction to a lot of reddit stories people call out as fake (as long as they don’t appear to be ones very obviously fake AND forwarding a bigoted agenda).

    So thanks for treating this one with the same amount of thought even if you had your doubts!

    1. Sweet 'N Low*

      Agreed! The world is a big, weird place and even if this didn’t actually happen to the LW, I’m sure it has or will happen to someone. Probably many someones.

    2. Boof*

      AAM is a nice advice column so I’m more comfortable with it here; reddit it’s just kind of annoying to have my attention sucked into something artificial since I find those kinds of threads end up getting highlighted to the exclusion of things I’m actually there for like local news chats, or gardening or something – but then I get distracted by the wild headline and story.

    3. Who knows*

      This is exactly why stories exist as a concept in human society. They teach us how to deal with situations we may encounter in real life – whether it’s the bogeyman, or just a human creep, etc.

  16. Not on board*

    Assuming this is a real letter:
    It is terrifying to leave a relationship where everything in your life is wrapped up in the other person, the comfortable life, the friends, etc. But look at this as an opportunity to build a life that is indpendant from a relationship. You may well end up keeping some of these friends, and you have the chance to make new ones.

    The issue isn’t that your fiance was a horrible person as a teenager (and a criminal too, as someone else said), but that they don’t really seem remorseful or adequately ashamed of themselves right now. They are upset because you are upset, otherwise, they actually wouldn’t think twice about their past behaviour.

    You can call off your engagement, mention it in passing to your coworkers (don’t include any info about your boss in this) and the news will make its way around to your boss. And act agressively normal with your boss and things will work out eventually.

    1. Carys, Lady of Weeds*

      This advice is great.

      My parents very much wanted me to stay with my ex, in spite of how desperately unhappy I was and had been for five years, because of the church we got married in. (The emotional abuse and constant manipulation was unimportant.)

      OP, it does get better. Even if your fiance never gave you any reasons other than this, this is still a valid reason to end the relationship.

    2. Christina*

      My only caveat to this is the framing of it as an “opportunity.” As someone who experienced trauma (not in the fluffy social media sense, but very real physical and psychological damage) and had people telling me to “use it as an opportunity to reinvent yourself! look at all the fun stuff you can do now! make new friends!” it feels very dismissive of the pain and damage in that moment.

      1. Not on board*

        I have experienced real heartbreak. Once some of the pain subsided, I found that framing things in this way helped me move forward. Also, it’s not clear that OP experienced real trauma, just that they were horrified to find this information about their fiance.

        I am not trying for even a nanosecond to be dismissive of the pain of this situation. I just think that mental reframing can help you heal and move forward. Also, the idea is to create a life that won’t be completely dismantled if you break up with someone, because it’s not healthy to make your partner your entire world.

        1. Christina*

          Sorry, I was definitely projecting some of my own stuff onto this. Yes, reframing can be helpful in finding your own strength, and important to build relationships and networks of support that aren’t connected to a single partnership.

  17. notagirlengineer*

    I would lean toward #2 with an added, “I’m sorry I unknowingly brought to the office a reminder of a horrible time in your life. I have learned a lot of valuable information, and I’m sorry it came at such a cost to you.”

  18. Retired Vulcan Raises 1 Grey Eyebrow*

    I couldn’t get over the repeated lying and then the gross minimising of actual abuse. He’s showing you how he still behaves and regards women.
    I’d dump him, but not the rest of my life, i.e. keep the job & coworkers, make new friends – which you’d have to do anyway if you uprooted your life and moved.

    When you talk to the boss, I’d use “dreadful bully” instead of “jerk”, as the latter now has a broad range of meanings, some of which are not very serious.

    1. Porque answer*

      I’m not sure how minimizing the abuse he used to inflict on a boy in school would be a “how he regards women” issue.

      1. LaurCha*

        Bullies have multiple targets. I’d bet dollars to donuts at least one of his was a girl.

        1. Porque answer*

          We don’t have any evidence of that, though. We just have the LW’s fiance bullying another male.

          So you have to add things that aren’t there to make this about how he regards specifically “women” vs. how he regards “men” or how he regards “people.”

      2. Ellis Bell*

        I read that as referring to the lying and would paraphrase it as “tells you how he still behaves, and it also tells you how he regards women” There’s a pretty big Venn diagram crossover of “guys who have horrifying behaviour around other guys” and “guys who have dishonest relationships/lie to women about their horrifying behaviour”. He behaves however he wants because he has no desire to be authentic; he thinks he’s cleverer than the person he’s lying to and he won’t get caught.

        1. Porque answer*

          “He behaves however he wants because he has no desire to be authentic; he thinks he’s cleverer than the person he’s lying to and he won’t get caught.”

          That’s not in the letter, though. We don’t know that he behaves however he wants or that he thinks he’s cleverer than anyone. We know that he was an awful human being in high school, and that her parents think he treats their daughter well.

          I’ve known many, many women and men who deny and minimize when called out on their BS. Most of them don’t get to the truth like this guy did. Liars come in all ages and genders.

      3. Retired Vulcan Raises 1 Grey Eyebrow*

        Persistent lying to his woman partner and trying to convince her that sending naked pictures of an unknowing victim was just another “prank” – I’d suspect he’d do that to me if we split up, so I hope he doesn’t have any of the OP

        1. Porque answer*

          Is he lying to her about it and being immediately truthful and taking accountability with the men who are close to him?

          We don’t know. There’s a lot of evidence in the letter on how he regarded others when he was in high school, but there’s nothing in the letter to say that he has an issue with how he regards women.

      4. Retired Vulcan Raises 1 Grey Eyebrow*

        Also the OP has just realised she has no friends of her own, only the same friends as he has. Sounds like he has isolated her, which would later help him to abuse her

        1. Porque answer*

          Isolating would be her having no friends at all. It sounds like her friends are all friends of the couple. She’s also friendly enough with her coworkers to want them at her wedding.

          She said nothing about abuse toward her. That’s fan fiction.

        2. metadata minion*

          It’s not that unusual to have friend circles mesh, especially if you’re not a social butterfly to begin with and/or met through mutual friends. I certainly think she should dump this guy, but that particular element isn’t necessarily a red flag.

        3. Lenora Rose*

          A number of my friends got together through our shared social group. My husband and I included. We do have individual members where one of us is closer than the other, but at least one couple who divorced would definitely have been described as having the same shared circle before the split.

    2. Just wondering*

      How he regards women? LW concealed boss’ gender, but give photos were taken in locker room, boss is arguably male (or at least, was at that time). Bad fiancé may behave contemptuous toward women too (or maybe not), but he is an unrepentant pig, either way.

      1. Porque answer*

        LW identified boss as a male: “Once, on a dare, he and his friends took pictures of my boss in the gym locker rooms and plastered his naked pictures all over the school.”

        But yes, unrepentant pig either way.

        1. Grizabella the Glamour Cat*

          Yes, he’s an unrepentant pig, all right. You seem oddly invested in defending him for some reason, which I don’t think he deserves.

          2. Porque answer*

            I said literally nothing to defend him. I made no excuses for his actions, and did not minimize what he did in any way.

            I see this a lot online. People subscribe to blanket/binary thinking, so they think you must be for or against someone. It’s actually pretty scary.

            **Molly is convicted of driving drunk after hitting a pole
            “Molly killed 3 people while driving drunk!”
            “No, no one died or was injured.”
            “Why are you defending her decision to drive drunk?”

      2. Moira's Rose's Garden*

        He’s at least contemptuous enough of the one woman we know about, to lie and attempt to gaslight her.

        “Treats women” is not a stretch just on the described. The first time someone shows you who they are, believe them. There’s no requirement to wait for a second round of: starting an argument to (bully) try and get you to back off, then revealing something terrible while trying to tell you it’s not terrible, all the while claiming “I’ve changed(TM)”. You’ve got 2 examples already (what he did to Boss, how he treated you), OP. Good luck!

        1. Porque answer*

          It would be very dangerous to assume that how someone treats one member of an incredibly diverse group is indicative of how they treat everyone in that group.

          It would be exactly like reading about a man writing in and saying his ex-wife treated him poorly, and concluding that she is awful toward men.

    3. Grizabella the Glamour Cat*

      Agree 1000%!

      If we could post images here, I’d post the famous nopetopus gif, as an illustration of what LW should do in terms of this engagement!

      (If anyone reading this is unfamiliar with this gif, just Google “nopetopus.” I guarantee it’ll come up!)

  19. Apex Mountain*

    It sounds like when you wrote this letter this all just happened. I might give it a few days or a week and see how your fiancee reacts/apologizes People are different than they were in High school, as horrific as he might have been back then. You are in a state of shock because he’s always been the man you love. Something he did decades ago doesn’t necessarily change all that

    1. Just wondering*

      Yes, yes it does “change all that” He is not the man you thought – just with a deep dark secret – he’s unrepentant, and either doesn’t understand how devastating these “pranks” were, or – more likely -doesn’t care as long as he can still buy himself the hot wife he wants. (And from here on out, after the wedding, he can be as awful – to wife or anyone else who gets in his way – and not even TRY to conceal it from her, because she married him *knowing what he is*)

      1. MsM*

        And because OP clearly won’t have her family to lean on if she desperately needs help getting out of there.

        1. Just wondering*

          True. (And even more novel-like, as the clueless and/or mercenary parents are a trope.)

          1. MsM*

            To be fair, they’re a trope because parents who value things like money over their children’s well-being and happiness are more likely to raise children who don’t see the red flags with partners who also don’t care about those things.

    2. mlem*

      This guy doesn’t see any problem with what he did. That means he’s NOT different than he was in high school, which means what he did “decades ago” is entirely relevant.

    3. HonorBox*

      People are different, yes. But committing crimes and then not being remotely remorseful about it is awfully telling. LW fell in love with someone who has now shown himself to be a different person.

      I think we’ve probably all done things we regret or would do differently when we know what we know now. But I think the vast majority of people who feel that regret/remorse didn’t do anything close to what the LW’s fiance did. I regret never coming clean about a prank… I sent a friend flowers on Valentine’s Day from his “secret admirer” but if I came clean today – 20 years later – I know him well enough to know he’d probably laugh, call me a couple of names, and laugh some more.

    4. MPerera*

      “I might give it a few days or a week and see how your fiancee reacts/apologizes”

      The thing about verbal apologies is… anyone can say anything.

      My father used to do whatever he wanted and then, when he saw that we were hurt or angry, he’d say he was sorry. This would immediately put us under an obligation to forgive him and move on, because otherwise we’d be holding a grudge. And needless to say, the cycle would repeat until I finally went no contact.

      Because of this, I’m cynical about verbal apologies, especially the sort which only come about because the wrongdoing was discovered.

      1. HonorBox*

        I had a teacher who said, “I don’t want to hear that you’re sorry. I need to see that you’re sorry.”

        It is one thing to apologize. It is another to understand that an apology goes further than those words. Being sorry involves making a change to behavior. And that has to last more than a few days or a week.

        1. Selina Luna*

          I keep telling my son, “It’s not enough to say you’re sorry; your behavior also has to change.” My son is 4, but I’m hoping that telling him this now will instill the idea that words are worthless when he hurts someone (emotionally, physically, or psychically).

      2. ThatGirl*

        I think verbal apologies are a usually-necessary first step, but they’re only as good as the change that comes with them.

    5. ecnaseener*

      For what it’s worth — high school was not decades ago, plural, for most people getting married. One decade, for the average person. If anything, given LW is being pressured to marry for money, I would guess she’s in a culture where people tend to marry younger.

    6. Snarkus Aurelius*

      He didn’t put a “kick me” sign on someone’s back. He stalked, harassed, and traumatized another human being. He committed crimes against another human being, and had all that happened today, the police would have been involved. Rather than take responsibility for his actions, he downplayed what he did tried to hide it. He’s not sorry at all.

    7. I went to school with only 1 Jennifer*

      Where are you getting “decades ago” from? Nothing in the letter mentions timelines in any way.

    8. NothingIsLittle*

      I have very mixed feelings about a hypothetical version of this, but in the letter OP says it’s been at least a few days because the boss was out of work and has now returned.

      On one hand, if the fiancé in a few days came back to the OP and said something like, “I’ve been telling myself since that time that what we were doing was harmless pranks, but telling you about it made me realize that what we did wasn’t harmless at all and I’m horrified by those actions. I’m doing x,y,z to get my head on straight/make reparations,” I could see postponing the wedding while you decide if your partner has grown enough as a person to be worth marrying.

      On the other hand, I’m not sure I as the boss could find out that the OP married the fiancé after learning about the bullying without believing she condoned the fiancé’s actions. I believe, in abstract, that people can change. But I’m also not sure if, in practice, my view of the person who chose to marry them wouldn’t be tainted.

    9. Ellis Bell*

      As bad as the high school behaviour is, the current behaviour as an adult is deeply worrying too.

  20. CatDude*

    “This is just the least horrific thing him and his friends did”

    This is the *least* horrific thing?! I can’t even imagine what the other things are.

    I’m glad the engagement is about to end, for LW’s sake. Hopefully the entire relationship will follow. It would be one thing if he acknowledged how much harm he caused and was trying to do better, but the fact that he tried to lie and minimize these as “pranks” tells you everything you need to know about his character.

  21. Hoary Vervain*

    Thanks, Alison, for acknowledging that something about the letter feels a little…scripted. I was thinking the same thing and it would have completely distracted me from the answer otherwise.

    OP, if you’re out there, please take this as a big red flag (especially your fiancé’s lack of remorse and unwillingness to accept responsibility) and rethink the relationship! Hopefully the work part will blow over.

    1. Observer*

      OP, if you’re out there, please take this as a big red flag (especially your fiancé’s lack of remorse and unwillingness to accept responsibility) and rethink the relationship!

      Yes, indeed. But also a red flag about your parents. It’s pretty clear that you probably will not be able to depend on them if things get tough for you. Do yourself a favor and build your own network of people who can depend on you and that you can depend on.

  22. YesPhoebeWould*

    Bullies almost never stop being bullies unless they are (literally) beaten into submission. If you are marrying a piece of garbage who did these things when he was a young adult (which juniors and seniors in high school are), then you have much bigger problems than your boss. Filth doesn’t stop being filth because time passes.

    He lied to you about being a bully. What else did he lie to you about?

  23. Dust Bunny*

    Taking this at face value: I never did anything remotely like this but I actually remember thinking when I was about 14 that if I weren’t me, I wouldn’t even be friends with me since I was so obnoxious.

    However . . . what really gives me pause is that your fiance is just stonewalling instead of processing this with you. I would be troubled if someone I loved had behaved this way as an adolescent but if they had some (a whole-a** lot) of insight into it and were prepared to sincerely apologize if the boss were receptive, I’d probably want some couple’s counseling, but I wouldn’t necessarily throw the whole thing out.

    But if they minimized it and expected me to basically just forget I’d heard anything, then, no, I would not be on board with marrying that.

    1. Laura*

      I am right with you Dust Bunny. I realize this is Ask a Manager so we’re rightly focusing on the work relationship, but in case the OP is reading I wanted to say that I think it’s worth giving your fiancé the chance to make things right. This could be going to counseling together, this could be saying to them “You know my work relationships are important to me, how do you think we can handle this?” And see what they say, maybe the offer to write a letter of sincere apology, maybe not, but whatever they suggest, when given the time and space to reflect and problem solve, will be telling. I can imagine that if they hadn’t thought about these incidents for a long time, and had distanced themselves from that part of their past mentally, it could have been very overwhelming to now have to face their past behavior with the eyes and mind of someone who can see how wrong it was. Being vulnerable and taking accountability are leaned skills. You certainly aren’t obligated to stick around while your fiancé learns them, and I definitely wouldn’t if they don’t want to, but maybe there are options for growth and repair here.

      2. Your Former Password Resetter*

        Uhh, no. He had several chances to react, and he chose to stonewall, lie, and minimize what he did. That is not someone who believes they did wrong, or who did the self-reflection and growing to change into a less awful person.

        And even if somehow in his deepest hearts of hearts he could somehow be convinced to stop being horrible with enough love and sacrifice and concessions… It’s not the OP’s job or responsibility to drag that out of him. He can go get a therapist and try to work this out.

        She has zero obligations to shackle herself to this burning dumpster fire of a human just in case he one day decides he might want to change.

      3. Observer*

        I think it’s worth giving your fiancé the chance to make things right.

        No. Not remotely.

        Here is the thing. The fiance *had* an opportunity. He could have admitted the situation instead of stonewalling. He could have admitted that what he did was severe bullying *at best*. But instead he lied, then stonewalled, then minimized some pretty horrible behavior in an extreme way.

        How can he “make this right”? And how can the LW approach him to give him this “opportunity” without giving him the tools to try to gaslight her or “just” make a bunch of good sounding excuses and take a bunch of performative and useless actions? Given that it’s a fair amount of time since this argument happened, and the fiance has not come up with any ideas to make things right, change his character, and / or show that he *actually* has changed, it’s reasonable to conclude that he actually does not see that what he did was so bad, and sees no need to change. Maybe he’ll pretend to keep the LW, but that is totally not helpful.

      4. Ellis Bell*

        Just in case no one has ever told you this; don’t ever, ever go to counselling with liars and/or bullies. It’s well established that counselling will be used against the most well meaning person; it is highly likely to make abusive and dishonest relationships worse, and a therapist won’t be able to help you in that format.
        Therapy is supposed to be a safe space, not to be abused by someone who is not taking the process seriously. Therapy isn’t magic, it’s supposed to be for people who will engage. If OP wants to talk to a therapist, she should go alone.

      5. C*

        Look. I’m not going to say that people can’t change, but for LW’s own peace of mind they should act as though Ex *won’t* change.

        Maybe some real world consequences will give him the impetus he needs to get his own therapy. Or maybe they won’t. But he’s not going to do it if LW decides to play Stand By My Man about it.

  24. Naomi*

    Alison has the work part covered. I’d just like to say, OP, I’m sure you feel like a wreck now but someday you’ll look back and say “thank God I didn’t marry that asshole.”

    When you feel up to it, I’d suggest finding a hobby or activity that gets you out of the house and gives you a chance to make some friends who aren’t also ex-fiance’s friends. In the meantime, therapy is probably a good idea, if only to give you a shoulder to cry on. Internet hugs if you want them.

    1. Productivity Pigeon*

      Yeah. Better call of the wedding now instead of fleeing in the night (maybe with a couple of kids) in five years’ time.

    2. Marion Ravenwood*

      In the words of Eric Church, “now I thank God I ain’t what I almost was”.

  25. I should really pick a name*

    Two huge arguments that should have just been conversations.

    That doesn’t bode well.

    1. My Boss is Dumber than Yours*

      And the very passive way she described them make it abundantly clear that this is a normal part of their relationship.

    2. Harper*

      Very insightful, and something I wouldn’t have noticed if you hadn’t pointed it out! Toxic people deflect, deny, defend, project, accuse. Healthy people listen to understand, reflect, and respond calmly.

  26. learnedthehardway*

    I’m going to assume that the letter is entirely real. Allison may have reason not to, but the situation itself isn’t extremely unlikely. Especially in a smaller town, there is a non-zero likelihood of encountering people who are related/engaged to people you knew in high school. I hear every once in awhile about my parents encountering people I used to know in high school. If I lived in that same community, I would undoubtedly work with / run into some people I knew.

    Anyway, the OP is now re-examining her relationship with her fiancé – which I think is warranted, given the fiancé’s inability / unwillingness to recognize, take responsibility for , and (at least) deplore (if not atone for) their past actions. That shows a serious lack of empathy. And there’s a streak of cruelty there that would make me wonder what this person will be like in future.

    I think – regardless of what the OP ultimately does – putting the brakes on the relationship and postponing the wedding is a good thing for her to do (for her own sake).

    WRT the OP’s manager – learning this information caused her to have a visible reaction and to take 2 days off work, and now the manager is avoiding you. That person was seriously traumatized by what your fiancé and his friends did. I don’t think being aggressively normal is going to work, here.

    At the same time, the manager did not speak with you or confide in you about the bullying, and letting them know you learned what your fiancé did to them really might make them MORE uncomfortable & upset.

    That’s another reason I would postpone the wedding – I would obliquely let your manager know that the wedding has been postponed, and that you’re dealing with some issues that have come to light. Leave it at that. The manager will read between the lines.

  27. Some IT Guy*

    LW, your soon-to-be-ex was distributing child pornography without the consent of the victim (in either the common or legal sense). He should be in jail, not your life. I doubt that getting law enforcement involved at this point would help, but feel free to mention to anyone who objects to your kicking this “man” out of your life that you don’t intend to marry a criminal.

    And I agree with other commentors that #2 is the better approach. The conversation will be hard, but your professional relationship will be better once it has happened.

      1. Harper*

        He distributed naked pictures of a teenager against the victim’s will. Can you understand the short-term and long-term ramifications of that for the victim?? It’s sexual assault. No, jail time is not too harsh.

        1. Apex Mountain*

          “Can you understand the short-term and long-term ramifications of that for the victim??”

          Yes of course. I was assuming the fiancee was a teen as well and so probably wouldn’t have faced jail time.

          1. Ellis Bell*

            While I wouldn’t expect this person to (still) be in jail, this kind of violent and sexual behaviour would be at least an arrest in many jurisdictions. Even if their age gets them leniency and a caution; it doesn’t seem to have happened at all here. He’s still acting like it’s a prank, with no awareness of the criminal nature of this stuff.

          2. C*

            Teens have been arrested and gone to prison for sharing nude pictures of themselves, let alone nonconsensual images of other people.

      2. Elbe*

        I honestly wish that people would involve real consequences more often in cases of bullying this severe. Even if it doesn’t involve actual jail, there should be some sort of legal consequences for a few reasons.

        1) The reason these behaviors come with jail time for adults is because they are deeply harmful to the victims, and it’s even more – not less! – damaging when the victim is in their formative years.

        2) The victim needs to know that the adults their society value them and will intercede on their behalf.

        3) Behavior this cruel needs to be nipped in the bud. A willingness to inflict this level of humiliation and pain on another person isn’t part of a normal development for kids. It’s a sign that something is really wrong and someone needs to intervene before the bully becomes an adult. Court-ordered therapy would be a huge help in getting the bully on a better path.

        2. Observer*

          A willingness to inflict this level of humiliation and pain on another person isn’t part of a normal development for kids. It’s a sign that something is really wrong

          Yes, this is true. And I wish that people would be more cognizant of this when the subject comes up.

          Bullying is never ok. But there is bullying and then there is . . . stuff like this. This is being a wing puller. And those people don’t change unless they put in a lot of work and generally they need to be *forced* to do it.

          That clearly has not happened here. So, LW, really think *very* carefully about what your parents are saying to you. Because either they are being really gullible or they are saying that it’s ok to tie yourself to someone who is pathologically cruel because he’s rich and gives you nice things. Neither makes me think that their advice to you is ever going to be sound.

      3. Snarkus Aurelius*

        Yes.

        If you doubt me, consider him doing the same thing today as an adult. He’d be charged with multiple crimes.

      4. Moira's Rose's Garden*

        Have you considered that maybe your tolerance for personal violations is a bit … below the bottom of what society in general should be ok with?

        Personally, I’m an abolitionist, but until we get restorative justice going, I’m very ok with jail for distributing explicit pictures of minors for public view.

        1. Apex Mountain*

          “Have you considered that maybe your tolerance for personal violations is a bit … below the bottom of what society in general should be ok with?”

          Not sure what you mean exactly but nobody should tolerate any personal violations

          1. C*

            Then exactly what consequence do you think he should have faced for taking nude (or at least, near-nude) images of another student without his consent and sharing them with other people, also without that student’s consent – or, for that matter, with the consent of the other students on campus who might not have wanted to see this.

            Since you think that jail is “over the top” you must have an alternative in mind.

            1. Apex Mountain*

              For a teen, yes I do think jail is too much at least if it’s a first offense. For an alternative, I don’t know…what are the options other than jail? Probation, Juvie, community service, fines, therapy, expulsion, all of the above?

              1. C*

                Juvenile detention is jail.

                Or, rather, it’s prison, which is where you go after conviction. Jail is for pre trial detention and short term sentences. “Juvie” is prison.

              4. C*

                > Probation, community service, fines, therapy, expulsion

                Probation from what?

                Fines that his parents pay?

                This leaves community service, therapy – which he ought to have been getting no matter what – and expulsion, and I’ll say outright that I don’t think expulsion is a good solution if there is no educational alternative.

                Nor do I think that community service is an acceptable punishment for the nonconsensual production and distribution of CSM, after an ongoing campaign of harassment against the victim.

                Those alternatives are for first time offenders who have commited minor crimes. That’s obviously not the case here.

                1. Apex Mountain*

                  You asked for alternatives – i’m not supporting or defending them, just listing them. Not a hill to die on for me

                  But I don’t see how you reconcile sending him to prison while keeping him in school.

              5. C*

                Prisons, including juvenile detention, have education. You can continue going to school while imprisoned.

                I can see that you feel strongly about this, but I’m beginning to suspect that you don’t know much about the topic.

          2. Snarkus Aurelius*

            Then why is jail “over the top” in your point of view? What this person did was a crime. What’s the alternative?

            1. Apex Mountain*

              For a teen, yes I do think jail is too much at least if it’s a first offense. For an alternative, I don’t know…what are the options other than jail? Probation, Juvie, community service, fines, therapy, all of the above?

              1. C*

                Adding to my previous clarification that one of those options is jail (prison), there is no way that was a first offense.

  28. AnonSurvivor*

    As someone who married this guy after her mother said, but…he’s okay to you…after he was awful at our wedding because it rained, LW you dodged a bullet. On a personal note, you may need some therapy to explore your relationship to your parents and their values. Took me a long time to untangle that. Also, you may lose many of your friends. I did. Americans (in my experience) love a rich man. Yes, my mom doesn’t talk to me, but still spends time with him and his newest fiance.

    I’m for #2 with the boss. I did #1 in work relationships, and it didn’t really work out. Without any outright repudiation of his behavior, I think people felt I was complicit even though we’re obviously two completely different people.

    1. Selina Luna*

      I actually broke up with a rich person because they were fantastic (and still are; we’re good friends to this day), but their parents were awful. Their parents are still awful.
      You’re right; many Americans will overlook a boatload of red flags if the flags are attached to a yacht.

      1. Bananapants Modiste*

        “many Americans will overlook a boatload of red flags if the flags are attached to a yacht.”

        Another AAM quote I need to steal for my collection! Thank you!

  29. zinzarin*

    “I don’t have any friends who aren’t his friends too.”

    This is alarming, and telling. He’s already successfully isolated you from your natural support network. I’m afraid that the general consensus on these board that “you’re next” is probably right.

    Get out–which you’ve already decided to do, but, don’t get cold feet–and have a conversation where you *thank* your boss for helping to bring this to light. Apologize for bringing up trauma, too, if it feels natural (you’re apologizing in sympathy, not for having done anything wrong).

    2. The Kulprit*

      Not necessarily. There are ways to end up with a joint friend group as a couple that don’t involve someone systematically removing everyone from a partner’s life that isn’t originally and deep down really, solely, *your* friend.

      I consider this a Yellow Flag; more information needed, but proceed with caution.

      1. Rebecca*

        Agree. Most of my husband’s friends are my friends, but I think that’s a problem and I want him to fix that. We moved to a new town recently and I am better at putting myself out there to make friends and I’ve brought some of them home, he is sort of waiting for it to ‘happen naturally’ and we’re too old for that now. There are reasons it can happen other than abuse, but it is situation that should probably be fixed.

      2. Pocket Mouse*

        The LW said they don’t have *any* friends that aren’t also his friends, not that they don’t have any *local* friends that aren’t also his friends, or that the friends in a given friend *group* are all his friends too. Presumably having some friends of one’s own going into a relationship and then no longer having those friends over the course of the relationship is a red flag. Or, if the LW’s friends morphed into also being his friends, they should be able to trust the LW and understand the situation well enough to support LW through the aftermath of the breakup.

  31. Ann O'Nemity*

    Saying nothing while my boss avoided me would drive me crazy. I’d want to address it directly with something like:

    “I wanted to check in because I noticed things have been different since we spoke. I had no idea about the history between you and [Fiancé], and I want to sincerely apologize if seeing that connection brought up painful memories. I completely understand if you need space, but please know that I have taken this seriously. I respect you and truly regret any discomfort this has caused.”

    I wouldn’t go into the stuff about the relationship ending. While the boss was deeply affected by the past, they shouldn’t feel responsible for the fallout of the employee’s personal life. Sharing this could make them feel uncomfortable, guilty, or even more distant.

    1. The Kulprit*

      I like this, its clear, closes the loop, but maintains the work|personal life boundaries by not giving boss any more info about OP’s relationship than needed.

  32. Kim*

    If you decide to call off the engagement, and if there’s any chance your fiance could retaliate against your boss, you have an obligation to let your boss know.

    1. MsM*

      Fair point, although I suspect the boss expects OP would have brought it up with the fiance and may be expecting some kind of reaction based on that alone.

  33. Mouse named Anon*

    LW – I would strongly advise you to get out now.

    1. If he truly did those awful things, and has no remorse he will eventually be a bully to you. It may not be apparent now but it will be eventually. If you want children he will also be a bully to them. Oftentimes bullying at home leads children to become bullies at school. Thus raising another generation of bullies.

    2. If he indeed is rich, he could make your life miserable if you want to divorce. He has the money, power and attitude to do it.

    3. Bullying does tend to lead to lifelong trauma. While I was not really bullied I have several close friends that were. Now even in their 40s it has let to mental health issues still. They still cry when they think about it.

    Good luck LW. I am not sure what to advise you about work, but I think Allison’s advise is sound on this one.

    1. Elbe*

      Good points. How would the LW feel if her future child did this and her husband brushed it off as “boys will be boys”? Parents have a tendency to pass along their views.

    2. Survivor*

      As an escapee from an abusive relationship, people who are bullies are often able to keep up a facade of being good, loving partners. He may be nice to you NOW, but abusers will drop the nice act once they see you are committed. Usually shortly after moving in or shortly after getting married.

      1. AnonSurvivor*

        Or commonly after you’re pregnant (where the leading cause of death is homicide). It just happened to a friend’s daughter, and it’s horrible to see.

  34. CzechMate*

    Yeah, I’d go with number 2. Since the engagement doesn’t actually seem to be off, you could adjust the script to say, “It was enough for me to have a serious talk with my fiancée and this is something we’re working on “as opposed to “it was enough for me to call off the engagement.”

    I actually don’t disbelieve this story at all–I’ve seen similar things happen in real life. Once, when I was an admin at a trade school, one of my 18 year old students started dating a much older, problematic student who I found out went to high school with my husband. My husband recognized him leaving the school when he picked me up from work one day. When he heard how he was as a boyfriend (I personally wasn’t involved in counseling the students, but I heard through the teachers that they had a volatile relationship. She was often sobbing in the hallways and once she cut class and got a face tattoo, I guess out of desperation and grief?) he went, “..so it sounds like Connor hasn’t changed.”

    1. Dust Bunny*

      Yeah, I think we’re just not used to seeing it written out so concisely. We all know of situations that resemble this, we just usually see them in parts over a longer span of time.

    2. Overthinking it*

      Definitely would NOT say “. . and this is something we are working on . . ” (that should be part of your apology to another parent when your toddler hits someone on the playground.) So, so much wrong with that: 1) the “we” implies LW has agency in the wrongs her fiance perpetrated; 2) it leaves the victim out and recasts the bullying as a problem primarily for the LW; 3) it implies the wrongs of the past can be fixed in the present. . . and the list goes on.

      But most damaging for the work relationship is: 4) the *we* are working on it puts the LW and fiance on the same side – and you don’t want to appear to be on the same side as your boss’ abuser – you just don’t! So, don’t use that wording. Please.

      If you HAVE to have a conversation with boss before you have made a clean break, maybe say: “This has caused me to seriously re-think things.”

  35. MicroManagered*

    I experienced this level of bullying in school and even though I live hours away from where I grew up, I actually have encountered a couple of the people who bullied me as adults through work. If this letter isn’t real, I would say it’s true enough.

    1. Productivity Pigeon*

      I could totally see it happening.

      I’m guessing it’s the addition of the fiancé being rich and OP’s parents not being bothered by the whole thing that’s pinging people’s radars.

      But that you can get engaged to someone and find out they did terrible things to someone you work with? Totally plausible.

    2. CatDude*

      Agreed, even if this letter itself isn’t real, the kind of situation they are describing is very real – so it’s worth discussing either way.

  36. Scarlet ribbons in her hair*

    “I learned enough to understand he was a jerk in school.”

    If someone was able to take pictures of you trying on bras in a dressing room (meaning that in some of those pictures, you were naked from the waste up) and posted those pictures all over the place, would you refer to him as a jerk? Or would you use a stronger word?

    Unlike Alison, I never doubted for a second that this letter is real. I guess it’s because I was relentlessly bullied by the vast majority of my classmates (approx 140 out of 150) from the eighth grade until high school graduation. The teachers saw it, and they did nothing. My mother kept telling me that the other kids were just teasing me because they liked me. There were many times that I thought of suicide as an option, but I told myself that I hadn’t done anything wrong, so why should I die?

    If any of them had regretted what they had done, they had every opportunity to call me and apologize during the summer after high school graduation. If they couldn’t remember my last name, all they had to do was look in their yearbook. But not one of them apologized.

    I feel bad that I don’t have any good memories of high school. Even the girls that I was friends with in grade school started bullying me. I never wanted to go to a reunion. I was terrified that if I tried sitting at one of the tables for dinner, I would be told, “You can’t sit there! I’m saving that seat for someone!” And then I would move to another table, only to be told the same thing. And I would wind up having tried to sit at every table and being rejected everywhere.

    I once read a question in Dear Abby written by someone who was bullied in high school but decided to go to the reunion. So he RSVP’d and sent a check. He said that the check was returned to him, along with a note requesting that he not attend. I don’t remember what Dear Abby said, but I remember thinking to myself that it was a good thing that I never wanted to go to a reunion.

    As already said, what is called a prank is really a prank only if the prankee laughs afterwards. LW’s boss did not laugh afterwards.

    If LW’s fiance honestly thought that what he did was pull pranks, I’m wondering if he ever pulled them on his friends. Meaning did he ever take naked pictures of his friends and post them everywhere? I doubt it.

  37. Joana*

    People absolutely do change, but when they do, they do tend to acknowledge that what they did in the past was horrific (or whatever level of not okay it was) and don’t try to downplay or hide it from people in their lives. Either he still does stuff like that and is trying to hide it from OP, or he doesn’t get that what he did were literal crimes (and in that case could start doing stuff like that again).

  38. darsynia*

    Alison is being very kind but certain behaviors are just intrinsic to a personality and are a full-stop, absolutely not kind of association. I often wonder if the girl who threatened my life and bullied me for my father’s death in high school is married to someone who knows that’s the kind of person she is.

    Good on the boss for being honest. Unfortunately, if this LW doesn’t break off the engagement, their personal reputation with her boss will be forever ruined (is that fair? no! but life isn’t fair, and it’s very realistic. I would see someone differently if they married my bully. In point of fact, I would never associate with them again, if I could help it). I hope that the professional reputation can stay intact either way.

  39. Definitely not me*

    When someone talks about their fiance and their marriage plans and they toss out the phrases “after a huge argument” and “huge blowup” like they’re a totally normal and harmless part of the relationship, I want to slap them and say, This is not the life you want. I didn’t even need to know about the bullying part.

    1. Observer*

      Good point.

      LW, one of your parents’ arguments for why you should stay with him is that he’s “good to you”. Someone with whom you are apparently having regular “blow outs” is not someone who treats you well.

    2. CommanderBanana*

      Right? I admit I read way too many advice columns (I’ve cut down!) and I don’t know if people are writing hyperbolically, but it seems like every fight is a meltdown or a blowup, everyone is gutted or devastated or crushed all the time, and everything is just so…fraught.

      While I don’t think arguing is inherently bad in a relationship, having huge blowups and meltdowns all the time is not normal or healthy!

    3. The Unspeakable Queen Lisa*

      Your response to signs of bullying/abuse is a desire to slap someone? You may want to look in the mirror, friend.

    4. Lenora Rose*

      I hope that “I want to slap them” is just poor hyberbolic phrasing in itself, but I do consider this to be an especially and moment to use that particular phrase.

  40. Trillian*

    I’m in favour of addressing it directly (if OP’s decision is to terminate the relationship). Bullying comes with enough rug-sweeping to give the target a permanent aversion to rug-sweepers.

  41. ecnaseener*

    I vote option 2, because it gives you the opportunity to make it crystal clear that your boss’s reaction was NOT the reason you broke up, your ex’s character was, you’re grateful to have found out about his character now rather than later. If you don’t spell that out, I worry the boss will be left thinking “oh god, did my employee torpedo her life because she was afraid I would hold it against her or something?”

  42. ElastiGirl*

    This horrible “prank” is just the one he’s willing to confess to. That means other “pranks” were likely much worse.

    Run. Call a therapist and get out of this relationship for your own safety and wellbeing.

    Please. We are all holding our collective breath for you

  43. Observer*

    I’m disgusted that the man I love and want to spend the rest of my life with could ever be this person

    This is really hard. But the thing is that his is not who he *was*, but who he *is*. NOW, in the present. Yes, he’s *smarter* now, so he’s less likely to do these particular things. But fundamentally, he’s the same person. Which is a real shock to the system, as he has managed to hide it so well.

    How do I know that he’s still basically the same person, just more careful and canny? Because of his reaction to your questions. He characterizes these actions as “pranks” and while he doesn’t want to discuss them, because he knows that other people will look poorly at them, he doesn’t seem to recognize that these are real issues. From what you say, he hasn’t given you any reason to believe that he’s done any work to change himself. That combination is really telling.

    LW, I know that this is hard to hear. But, I repeat: you need to know that this is not who he *was*, but who he *is*. Just smarter. Which means also, more dangerous. If he ever turns his ire on you, you can be sure that he will be a lot more clever and sneaky than he was a HS student.

    Get out while the getting is good.

    1. Dust Bunny*

      If he’s not owning it, he’s still that person.

      Also, her parents want her to marry that person, so that’s another relationship to run by a therapist.

  44. No one you know*

    I have to agree with others that #2 is the best option.

    My spouse was badly bullied in HS. He has never revealed to me the details but has basically said, his bully should have been arrested and put into jail for his actions.

    Several years ago, my spouse’s bully was on a television show featuring wealthy people doing good deeds for people in struggling situations. The bully was one of the wealthy people. We watched the show, my spouse wanted to see it, and the bully was portrayed as a wonderful, caring person. When it ended, my spouse basically said seeing the show and how the bully was portrayed didn’t change a thing, he felt that his bully was still a horrible person who belonged in jail and nothing would change his perception or feelings. And this bully did not deserve success or to be portrayed as a good person.

    To this day, I have no clue what this bully did to my spouse, but for my spouse to feeling so strongly and hateful toward a person decades later tells me it had to be horrific as I’ve never seen him react with such hate toward anyone ever. So, if the plastering naked pictures of the boss was the least horrific thing he’d done to the boss, I can understand why the boss is reacting the way they are. The best thing for OP and their relationship with their boss is to distance themselves from their fiancé and ensure their boss knows they have parted ways.

    1. Boof*

      My husband has said that he had bullies who actually urinated on him – shades of the bullying in some movies like kung fu hustle etc I imagine. I didn’t think that was actually a real thing until my husband mentioned it – he was a tall gangly adhd dude – easy to rile up + stuck out in a crowd and socially awkward. He felt like moving schools changed his life away from being near suicidal as he was able to leave it behind effectively.
      I will accept that middle school is a time when kids are way more terrible than they will be as adults – some folks tried to bully me in the “I don’t find you attractive” way but I just… didn’t care and it never got physical so for me it didn’t phase me much. I’m pretty sure most of those people are not terrible people just learning boundaries at the time in a really bad way.

      1. No one you know*

        My husband started kindergarten at age 4 and college at 17. This was back in the early 80s when the cut-off birthdate for starting kindergarten was end of the calendar year. Add on that he was in the gifted program, not athletic at all, and was small for his age and very skinny. That combo in the late 80s/early 90s for a high school boy basically made you a target for bullies. Along with being a Gen-Xer/Latchkey kid that basically was pushed out the door in the morning by your mom and only came home to eat and later when the streetlights came on, you were left to run around town all day long either on your own or with your friends. He grew up in a smallish town, so it wasn’t always easy to hide from the pack of bullies that were out looking for their next victim. I too was bullied in HS, but not nearly as bad as he was. Thankfully my bullies lived in another town (I grew up very rural, so my HS consisted of kids bussed in from multiple towns) so I rarely ran into them outside of school except at school events. I was also shy and a bit of a loner, so I spent a lot of time exploring the woods around my town, which made it easy to avoid people.

    2. Snarkus Aurelius*

      One of my former bullies is also considered a really kind and wonderful person today. She was so awful to me that I don’t really care how she is now. When she ran into me a few years ago, she acted as though we’d just lost touch. I gently reminded her this was not the case, and I didn’t want her to contact me ever again. She was surprised but not that surprised.

      1. No one you know*

        The “former bully turned kind, wonderful person” is always an interesting one to me. My career job shortly out of collect hired a college grad after me and she was a horrible coworker and person. A few of us entry level employees shared an officespace and this woman would spend most of the day talking/texting friends and shopping online. She’d spend 45 minutes every morning deciding where to go to lunch with a couple coworkers, then would disappear for over an hour during lunch and come back and eat lunch at her desk, while not working. She was petty, rude, passive-aggressive and would belittle people all the time. She was the type who would be super rude to the waitstaff at a restaurant and if someone said something to her about it, she’d basically say “Who cares, they’re just a waitress and here to serve me!” At work, she’d get the interns on her team to do most of her work but take credit for it. Her boss was clueless and thought she was great. Yet most people working with her or sitting in our office area couldn’t stand her.

        Fast forward 15+ years, she’s moved on and up in her career (how?!?!) and also started a non-profit in her current state, which I have to admit the non-profit is a great thing. She’s won all sorts of awards and has been a guest speaker at various events focusing her kindness in helping others and being a notable woman. I used to be connected to her on LinkedIn and every time I saw her share something about some award she’d won or some event she spoke at or being featured in some magazine/news story, I couldn’t wrap my head around her being the same person I worked with that honestly was horrible and not nice and not great. Maybe she had some major lifechanging experience I know nothing about but the person she supposedly is now does not come close to matching the person I knew her to be 15+ years ago, when she was an adult!

  45. Llama Llama*

    When I was young, a psychopathic boy killed a bunch of rabbits in the woods behind our house. It was a huge deal (and was even in the newspaper). I don’t remember his name but my sister was in the same grade as him (at a small elementary school!) and remembered him.

    She worked with his wife! When she found out the connection she very much judged the girl for marrying a psychopath. She didn’t know if the the wife knew but still kept her distance.

    All that to say, it’s not a stretch that this could happen.

    1. Ellis Bell*

      Some people live larger in our memories, and that’s why it’s so easy to recognise them later on, even with such a slim degree of a connection. I bet I have been shown countless pictures of people I went to high school with, or they’ve come up in the crowd on other people’s social media, and I just don’t recognise them. How often have you found another person from your home town or high school or college at a party? We cross paths with people from the past more than we think.

  46. Festively Dressed Earl*

    Why not both options?

    Start with #1, treating Boss as a valued and trusted colleague, but giving them space to process this.

    Take option 1.5 in the meantime: make a plan to live independently of Bullyboy financially, socially, and emotionally. LW should do this even if Bullyboy starts making real movement towards self-awareness, personal responsibility, and generally getting into glassbowl-rehab mode. Since LW and her colleagues are close, the news that she and Bullyboy are (hopefully!) dunzo will inevitably come up organically, Boss will put two and two together, and hopefully his relationship with LW will shift back towards normal.

    Once that happens, take option 2, but with two extra points: do it at the end of a workday to give Boss some time to process – if not an in-office meeting, maybe a quick coffee or drink after work Friday. I agree with the other commenters that LW should let Boss know that he helped open LW’s eyes about Bullyboy, but “thanking” him seems off to me. It could be interpreted as “Hey, your trauma was super-helpful to me even if it’s incredibly painful for you!” Maybe something like “Your reaction inadvertently led me to avoid a huge mistake, but I’m still so sorry you went through that.”

    P.S. If Bullyboy starts making noise about wanting to make amends with Boss, LW should not facilitate it, even something as ‘small’ as asking Boss what Bullyboy could do to atone for his actions.

    1. Observer*

      If Bullyboy starts making noise about wanting to make amends with Boss, LW should not facilitate it, even something as ‘small’ as asking Boss what Bullyboy could do to atone for his actions.

      Yes! This bears repeating, because it really is important.

      Also, if he does that, understand that this doesn’t actually mean that he wants to make things right. More likely that he’s trying to play *you*.

  47. Dr. Rebecca*

    Nothing to add to the advice, just…*wincing* on your behalf, OP. You’ve been really brave and highly ethical. I’m sorry you had to be.

  48. Calyx*

    I suggest thanking your boss. You could do it in person or maybe an email if they’re avoiding you. Something like, “I want to thank you for letting me know what Jim did to you in high school. I forced to tell me some of the details and was so disgusted that I broke off the engagement. It’s hard, and I wish you had never had those experiences, but given that you did I’m so grateful to you for letting me know before I was legally tied to a person who would do things like that. Again, I’m so sorry that you went through that and that you had to be reminded of it.”

  49. Jane Bingley*

    When my husband and I were dating, we were sharing about our childhoods and I talked about my experiences with being bullied and how formative they were. That conversation made my husband realize he’d been a bully to a classmate in his own childhood – nothing nearly as evil as the crimes described in the letter but definitely cruel. It weighed heavily on him. He ended up reaching out to his victim and apologizing for his behaviour. Now, even years later, he will occasionally talk about how he wishes he could go back in time, how he thinks about his victim and hopes he’s doing well, and how he wants to use his own experience to help our kids understand why bullying is wrong.

    That’s what changing and growing up looks like. Defensiveness and arguments are not it.

    1. I'm just here for the cats!!*

      My mom, who was graduated high school in 1980, had someone reach out on facebook. She had made a comment on a mutual friends post about bullying and something made the guy realize how horrible he and his friends were to my mom. He apologized and said it didn’t fix the past but he wanted her to know how sorry he was. It really amazed my mom and she felt, not happy, but a little better that it was acknowledged and she thanked him.

      Perhaps your husband could do something similar. Not in a way to make himself feel better or try to make up to the other person, but as a way to acknowledge his wrong doings. As long as he makes it clear that he is not looking for forgiveness or anything.

  50. ChurchOfDietCoke*

    When I was at school, a group of us took the middle out of our friend’s blue Bic biros and replaced them with red middles.

    That is a ‘prank’.

    What OP’s (hopefully ex-) finace did was a criminal offence.

  51. SteveG*

    We’ve seen former bullies in AAM before, and the throughline appears to be a complete unwillingness to accept the idea that it’s not, in fact, inherently unfair that there could be consequences for their actions.

    1. Snarkus Aurelius*

      I’m not close to my parents, but when I found out a former bully was a nurse who was providing care to my mom, I immediately contacted the hospital to say this woman was to go nowhere near my mother. I explained this person had over a decade of bullying me with little to no consequences that affected her behavior. The only reason she stopped is because we graduated and went our separate ways rather than her doing it of her own volition.

      I have no idea what happened to her, and I don’t care. The hospital made sure she didn’t have contact with my mom.

      If nothing else, lessons like that should be a deterrent for bullies.

      1. Elbe*

        Interestingly, I read an article about a study that found that male bullies are disproportionately likely to go into policing and female bullies are more likely to go into nursing. It appears to be a trend that these professions attract this type of person.

        1. CommanderBanana*

          That doesn’t surprise me at all – they’re professions in which you have a lot of power and control over other people. I’ve also read that bullying is a huge problem in the nursing profession and drives a lot of people out of it.

          1. Elbe*

            Yes, when I read the article I wasn’t shocked at all. It does make a lot of sense that bullies would gravitate toward environments where they have a lot of power and control, but also have the guise of being caring, helpful people. It’s a perfect choice for people who specifically want to have a positive image, for themselves and others, while still having the benefits of that kind of power.

        2. juliebulie*

          I never heard that before – but as it happens, my bully went on to become a nurse.

    2. Elbe*

      100%

      Even when they understand that their behavior had really severe consequences for the people they bullied, they balk at their behavior having any negative affects on themselves. It’s so common for them to frame what most people would consider the natural consequences of their actions as a punishment that a bitter, vindictive person is foisting upon them.

    3. GammaGirl1908*

      Ugh, this. Each time someone here admits to bullying, or doing something truly awful (Sylvia’s ex leaps to mind), not only are they totally astonished that it’s coming back to bite them, but deep down, they don’t really think what they did was all THAT bad. That all goes double if the victims are now doing pretty well for themselves, which means they should have gotten over it. They’ve whitewashed and minimized and justified it, and now it was so long ago that they can hand-wave it away.

      There was a letter to another advice column in which a husband had left his wife for his mistress a few years prior because the wife had miscarried a pregnancy, and the mistress was expecting. He was writing because he was very upset that the wife now had written a book in which he was the thinly-veiled villain. He was like, “Am I doomed to be the villain in her mind, like, FOREVER?” Yes. Yes, you are.

  52. Why Am I Like This*

    I also picked up on the OP having no other friends than her fiance’s friends. I bet if she looks over the life of this relationship, she will see that this is not the first red flag.

  53. Anon this time*

    Life is strange. My cousin ended up marrying my high school bully and it’s just horrible. Much like OP’s fiance, “Tina” claimed that she did not remember me or being a bully to me. After 3 months of no contact, she said she thinks recalls being in some classes with me. And it went in that vein until she finally said she remembered, but she didn’t think it was a big deal, just “kid stuff” and I needed to get over it. Well I haven’t gotten over it. It left emotional scars and still affects me to this day. I wished them well and went no contact. I didn’t attend the wedding, didn’t attend the baby showers and do not attend any events that they come to. Another cousin that is my age and we attended high school together also remembers Tina and from what I can tell, called her out every time something about me/my absence came out during the wedding planning process until she was uninvited. I’ve had numerous family members ask me if I can let it go for the sake of “family” and I say no and tell them if they ask again, I will go no contact with them.

    If this is real letter, I urge OP to postpone the engagement and think very hard about what you have found out. I don’t think there is a way to come back from this. Good luck to you.

  54. Not A Manager*

    Maybe I’m naive, but I find this story believable. Especially compared to things like “my CEO is my secret half brother,” or “my boss wants my kidney.” (Both of which I also believe!)

    I don’t like option 2. Even though the boss has nothing to be ashamed of, having been bullied and humiliated can feel humiliating even when you know better, and having to explicitly acknowledge that OP knows the details might be very hard for him. I’d choose a middle ground between 1 and 2. I’d (a) break up the with fiancé – why is this even in doubt? and (b) tell the boss in person that “after additional thought” you’d decided to break off the engagement. “He just wasn’t the right person for me.”

    1. Green T*

      I like this script but with the addition of just saying it publicly to the office, since she’s sent out save the dates. It wouldn’t be odd to say “Sorry, since sending out the save the dates I’ve ended up calling off the wedding. it’s always after you send the invitations, right?” I would keep it light and I imagine everyone will take their cue from that and if the boss wants to bring it up or pretend it never happened then they get to choose, as the person impacted by the bullying, provided that it doesn’t change the relationship. If someone really presses on why then that’s kind of a separate problem but I wouldn’t preempt it. People call off weddings for all sorts of reasons. I would probably respond to a but WHY did you call it off with “I decided I didn’t want to be married to him, so it’s kind of a critical step!”

  55. Elbe*

    I think it’s important to note that this level of bad behavior is not really in the realm of what most kids do when they’re learning and growing. Everyone can make mistakes and be mean to others, but not everyone regularly targets a person for literal crimes over the span of years.

    As I’ve gotten older, I’ve come to realize that significantly above average cruelty and callousness are some of the hardest things for a person to change, and it rarely happens. People often improve, or adjust their behavior to fit adult social norms, but it’s hard to be a truly decent person when you’re starting from such a low point. Being able (and willing) to understand and empathize with others is a crucial part of a person’s ability to grow. Having a cruel mindset during their formative years can really warp a person’s perspective, to the point where they just don’t absorb life’s lessons the way that other people do.

    All of this is to say that the LW should trust her instincts and not let her parents or fiancé try to downplay this. It’s easy for people to try to minimize what happened, or to focus on the fact that it’s so long in the past. But not feeling remorse for inflicting this level of harm is truly a red flag. If the LW wants to end the relationship over this, she shouldn’t listen to anyone who tells her that she is overreacting.

    1. Retired Vulcan Raises 1 Grey Eyebrow*

      Yes, this was prolonged cruelty, not just an isolated incident resulting from a loss of temper. Clearly no genuine regret, so likely to abuse again when someone is at his mercy. Run, OP!

    2. Snarkus Aurelius*

      Additionally, there was nothing in this person’s brain or conscience that ever told him to stop his cruel behavior. To go that long hurting another person without having an ounce of empathy or compassion or real consequences means they never learned that behavior was wrong, only socially unacceptable.

  56. pally*

    Just speaking for myself. Having been bullied in the past, #2 would be lovely to hear. It would assure me that OP was not in league with the bully. Because that would be my biggest fear.

    Not in any way knocking #1.

  57. Cat Lady in the Mountains*

    I was thinking about the work piece of this a lot, and I keep coming back to “what if the LW didn’t want to end the engagement – how would that change the work advice?” Because ultimately, for an employer or manager to have a staff member’s relationship choices influence their standing at work gets into some pretty questionable territory. And to be clear, this dude sounds horrible and I absolutely think LW should call it off. But I’m also imagining other scenarios where the LW might not be able to call it off for any number of reasons, and I really don’t want that to be their boss’s business.

    That leaves me coming down on the side of “aggressive normalcy” rather than “direct conversation.” I think the direct conversation just invites more intertwining of the business and personal, which the boss might appreciate on a human level but could have unintentional consequences for them to be able to navigate this professionally. As an extreme example, what if the manager has to lay off the LW in the near future? How much is “I just revealed something leading to the collapse of their relationship and now I’m taking away their job” going to influence their thinking?

  58. Nonprofit Lifer*

    I don’t think you’re limited to #1 or #2. You have a beautiful excuse to mention it without referencing their reaction, you just tell the boss and all your co-workers that you need to retract that save-the-date you sent around as the wedding is off.

    If the boss wants to inquire as to why, they can do so, but they don’t need to.

  59. Mark This Confidential And Leave It Laying Around*

    I dealt with significant bullying but the pictures are next level. That kind of targeted abuse is scary. LW, it might seem like overkill if your fiancee has always treated you well, but take steps to protect yourself, your pets, your property, and delete any photos this guy may have that you don’t want all over social media.

  60. Apex Mountain*

    Hopefully the boss is doing ok. Having to take two days off after this, I assume he was really shaken

  61. Kella*

    OP, to validate that breaking off this engagement (and probably relationship) is the right option and does not at all reflect badly on you: Look at the behaviors he’s exhibiting *right now*. He lied to you, point blank, about something important, in order to avoid having to be accountable for his own actions. Expect him to do that about things that impact *you* going forward.

    Then, he dramatically minimized the severity of the negative impact of his actions on another person. Part of what enabled him to do those horrible things back then was not taking that impact seriously. So that aspect of him has not changed. Expect that if you go through something awful that negatively impacts him, he will probably minimize your suffering in order to prioritize himself.

    So that’s 1. Lying 2. Avoiding accountability 3. Displaying apathy towards the suffering he caused others. Those are all pretty central behaviors for long-term bullies. The only other ingredients of a terrifying bully your husband hasn’t displayed yet (at least that we know of in this letter) are actively enjoying the act of cruelty on others and/or being controlling of others’ actions. To me, the first three are already deal breakers. But it may validate you to look over your past relationship and see if you notice any examples of the last two behaviors, too.

  62. Sparkles McFadden*

    So sorry you are going through this LW, but I really do think it will be a good thing that your fiancé’s past came to light. Better to know this now and not after the wedding.

    I think the first thing you need to do is make a quick “ripping the bandage off” announcement at work, saying “Please toss out those ‘save the date’ cards as things have changed and I really don’t want to get into it, thanks.” You have to do this even if you decide to go through with the wedding because you cannot have your work life intersect with your personal life *at all* if you marry this person and are still at this job. If you ultimately choose to marry the guy, I think you really do need to find another job because you will basically have to avoid mentioning your spouse at any point in time.

    While I don’t condone your boss’ freeze out behavior, I do understand it. I think you do need to say something such as “I am sorry I opened up old wounds. I want to thank you for being so open with me because you gave me so much to think about when you could have just said nothing. I want to thank you for trying to help me and I hope we can continue to work well together.” If you do dump the guy you can add that the boss helped you dodge a bullet. Though I’d like to keep this purely professional advice, I have to say that the fact that your entire social circle is your fiancé’s social circle is really disturbing. Even more disturbing is the fact that he is downplaying his horribly abusive behavior. People like this don’t change. They just pick new targets.

  63. Not that other person you didn't like*

    OP, let’s approach this very practically (it’s a highly charged emotional situation and it can sometimes be helpful to just look at it bluntly):

    You seem to have two options:
    1. Marry this guy and get a new job
    2. Cancel the wedding, send a “never mind that save the date note” to everyone, and decide whether to have a followup convo. with your boss based on your relationship with him

    But whichever choice, you need to make it soon.

  64. SunnyShine*

    This letter is written by AI. It’s a fun thought exercise though.

    Examples of why:
    “It was like the smile literally slid off their face. I asked if they were okay, and all they said was: “Is this who you are marrying?” I was really confused and had a very bad feeling.”
    Strong feelings, awkward descriptions to be dramatic.

    “My fiancé claimed to not remember them, but clearly he recognized them. After a huge argument,”
    Random huge argument with no information.

    “We had another huge blow-up and only when I threatened to walk out did he reveal the full extent of these pranks”
    Coercing her fiancé for information when the only fact she had was a weird look from her boss.

    “I returned to office the next day and requested to meet with my boss. My boss wasn’t in the office, and in fact took the next two days off. When they returned to work, they did not really engage with me or even look in my direction.”
    More dramatics based on little facts.

    “Now I am unsure what I should do…. My parents are telling me to move and find another job and marry my fiancé because he is rich and treats me well.”
    Doesn’t know what to do in cases where it’s clear. Even more dramatics involving family that doesn’t make any sense.

    A lot of AITA Reddit are in these styles. You can take some of the elements, run it through chat GPT and ask it to write a Reddit style post. You’ll get a similar story. I’m not saying anyone can’t enjoy this. Just wanted to let people know how to spot this stuff.

    2. Sparkles McFadden*

      Well sure, but the world is such a weird place that answers to made up scenarios can be useful to someone somewhere. Every AAM letter could be fake and it would still be a great site because the advice and discussions relate to things that could be going on at many workplaces.

    3. C*

      Any letter or post anywhere could be fake, made up by AI or by a bored human. It’s a problem at least as old as advice columns!

      This one at least probably applies to somebody else in the commentariat or a lurker – it may not have happened for real in this letter, but something like it has definitely happened to somebody somewhere.

  65. Moira's Rose's Garden*

    OP, there’s been great advice about how to handle at work, and the only thing I would add is maybe this would be something to give HR a head’s up about it as well. If only so that it’s been flagged in case boss’s reaction continues or worsens enough to affect your ability to have a healthy working relationship with them.

    As for (hopefully ex) fiance; I did some volunteering for an interpersonal violence hotline. One of the things we learned in training, is that *if* someone has those tendencies (and verbal abuse like having a shouting fight instead of a conversation VERY MUCH COUNTS!), they tend to worsen or accelerate after relationship benchmarks. Marriage and pregnancy being two of the biggest (moving in the 3rd). Leaving sooner can be harder because people may not understand (or have “notthatbadism”s for you), but it’s easier and will spare you a LOT.

  66. LadyHouseOfLove*

    If this fiance was willing to publicly post nude photos of a classmate without his consent, I don’t trust him not to cross the line with his wife.

    I heard too many stories of women having a kind wonderful male partner but as soon as they married or she got pregnant, the mask was off and he was abusive.

  67. Mutually Supportive*

    This could have been *even worse* if the boss hasn’t seen a photo before the engagement party/wedding

    1. I'm the cracker-eater*

      And weird that it was the fiancé’s photo, rather than the his NAME that triggered the reaction, right? (And normally, wedding invitations/save-the-dates don’t even include *photos* . . so . . . ?)

      1. Ginger Cat Lady*

        He asked to see a photo *because* he recognized the name and wanted to be sure it was the same person.

      2. Lenora Rose*

        There are an astonishing number of people with the same name out there. There’s someone at my workplace with the same name as a high school peer (not bully), but I’m fairly sure he’s not the same person.

        1. EvilQueenRegina*

          I can remember someone I used to work with being a bit apprehensive on hearing that new employee “Fergus Smith” was starting because she’d been at school with a Fergus Smith who she couldn’t stand. On the day, a different Fergus Smith who she’d never met before walked in. So yeah, I can see Boss hearing the name and wanting to check whether it was the one from school.

  68. Jasmine Clark*

    Maybe this letter isn’t real, but just in case it is, I wanted to respond anyway.

    First of all, you have to decide whether or not you’re going to call off the wedding. Seems like you’re thinking about it but haven’t actually done it yet. I hope you will call it off and end your relationship with this person.

    After you’ve done this, then let the boss (and other people you’ve invited) know that you are no longer in a relationship with the person. I think the boss will feel relieved to know that you don’t want to marry the person who used to bully him.

    I agree with Alison in the sense that I’m concerned that he’s minimizing his behavior. He tried to deny even knowing your boss! Then he tried to describe what he did as “pranks.” These are enormous red flags. I feel like if you were to marry him, he may not treat you well. It’s disturbing that your family wants you to marry him (so what if he’s rich???).

  69. Acbrn*

    I believe this letter writer because I’ve known several of her.
    The one whose life most closely matches hers married the mole because her parents told her to despite her reservations, and had to leave the state and her own family in order to leave him.

  70. Charly*

    #5 might have to talk to Boss eventually if they continue to not engage with them at work. Definitely Boss has a right to some space and consideration, but being ignored by 5’s supervisor might interfere with 5’s work if it goes on long enough.

  71. Raida*

    No need to leave the job.

    Get a coffee with your boss and say “I saw your reaction to Fiance’s photo, asked him about it, and learnt about the “pranks” in school which sound a lot more like “persistent bullying, harassment and torture” so I’m… yeah I’m probably breaking up with him. Just want to let you know that there won’t be an invite to the wedding or any other event where he’d be in attendance.
    And I’m sorry for inadvertently bringing up some *shitty* memories, especially where you have to keep your professional work face on.”

  72. TMarin*

    I support whatever the letter writer’s decision is. Sounds like a lot of trust was lost. That said….
    It confuses me that many people believe that convicted criminals can reform and become good people, but those same people (don’t know if there are any of them here) believe that the fiance’: once a bully, still a bully. I think that the fact that he didn’t want to come clean about it reflects his regret of who he once was (and was he the ‘gang’ leader or a ride-along?). However, his reluctance also destroyed trust.
    I just happen to think/hope that the fiance’ is now a diff. person, and I think he has paid a decent price for what he once was.

    2. metadata minion*

      I absolutely believe that people can change, but someone who describes that kind of behavior as a “prank” and doesn’t express any remorse (at least, that the LW describes, and since she had been ready to marry him I would think she’d want to show him in the best light possible) has not changed.

    3. Lenora Rose*

      Reformation starts with admitting to the wrong, and recognition that it was wrong. Where are you seeing this part, and what is your hope the fiance is different based upon?

      Nor does accepting a person can reform and become a better person obligate anyone to continue to associate with the person.

  73. dump him!*

    Honestly, I think a good middle-ground option could be to dump your jerk fiancee and cancel the save-the-dates with little fanfare. Your boss can probably extrapolate that you don’t ally yourself with a bully from a calm “The wedding is off, so un-save the date” without having to have a conversation that opens up old wounds.

  74. Witch of Oz*

    The fiance was a child and did childish things and was embarrassed about them as an adult. This was a shock to OP because she’s never witnessed this type of behaviour from him. It’s not like she went “Oh yeah. Makes sense. I’ve seen the way he treats people.”
    It’s concerning that her parents think she should go through with the wedding because the fiance is rich. It’s concerning that she doesn’t apparently have any friends of her own. But if she loves her fiance, why should she break up with him because he behaved childishly when he was a child?

    1. Scarlet ribbons in her hair*

      I don’t consider posting naked pictures of someone everywhere to be a childish thing. If a sixteen-year-old took pictures of you trying on bras in a fitting room (if you are a woman, that is) or pictures of your wife or mother or sister or female friend, would you be defending him by saying that he was a child doing childish things?

      1. Witch of Oz*

        Yes because a 16 year old is a child.
        People’s brains are not fully formed until they’re in their twenties. This is why teenagers aka children do silly things and make silly mistakes. They don’t understand consequences.
        The whole point of childhood is to grow up and grow out of it.
        When I was at school there were certainly some “mean girls”. Maybe some of them are still mean, I don’t know. But I hope they grew out of it. And maybe they feel ashamed of mean things they said or did as children at school. But they were children, not adults. Doing bad things does not magically make you an adult.
        And btw, if an adult took inappropriate pics of a 16 year old child and disseminated them and tried to use the defence that the 16 year old gave consent, what would the response be? S/he can’t give consent because s/he is a child.
        If you’re a child when someone does something to do you, you’re not magically an adult because you do something to someone else.
        I think TMarin made an excellent point. If criminals deserve a second chance (and I believe they do), why doesn’t OP’s fiance?

        1. GammaGirl1908*

          Frankly, because you don’t need to marry someone to give them a second chance. A second chance refers to going about in society and not being imprisoned after you have paid your debt to society for your crime. It doesn’t mean that you now have to have that person in your bed.

          This relationship is not a court of law, and she is not obligated to give him due process. LW does not need to legally bind herself to this man if she is now uncomfortable with his past behavior, which she is. She can break up with him for any reason, and if this is the reason she chooses, so be it.

          As pointed out many many times upstream, this is all amplified by the fact that he tried to hide and minimize and whitewash and trickle-truth the real story, which is so awful that we only have a tiny bit of it here, and that tiny bit involves sexual humiliation and violence. He doesn’t actually think there was anything all that bad with his past behavior, calling it just pranks.

        2. Fiorinda*

          A sixteen-year-old is not a child. A sixteen-year-old is a teenager. We expect more understanding of the world, consequences and basic human decency of teenagers than we do of children, because they’ve had more time to learn them in.

        3. metadata minion*

          I’m really concerned that you’re describing this as “silly” and “childish” rather than cruel. A silly childish mistake would be pasting naked pictures of *yourself* all over the school. Sure, he didn’t have an adult’s full maturity, but most teenagers manage to get through to adulthood without participating in extensive harassment that could have been criminally prosecuted.

        4. C*

          If OP’s fiance did what he’s described as doing then he is also a criminal.

          And, as a society, we generally give convicted criminals a second chance when they’ve done at least one of two things – served some sort of legal consequence or expressed heartfelt remorse and shown both a desire and a willingness to change.

          OP’s ex appears to have done neither of those things.

        5. Lenora Rose*

          You’re misreading and misquoting the brain study, which does not actually say brains stop developing at 25. The study ended at 25, and brains continuing to adapt and change does not mean a basic capacity for right and wrong is unattainable before then; a huge number of teens wouldn’t have posted someone else’s nudes because they already knew bullying was wrong.

          And despite how victims of bullies often feel, schools don’t give this stuff a pass because “oh, kids”; they spend a LOT of time trying to figure out the balance of clear consequences for harm done with the capacity of the child to learn to do better.

          More, if a teen breaks the law, they may not face the exact same consequences as an adult due to the greater possibility they can reform, but they do still face consequences.

          Capacity to consent is a consideration for the victim, not the perp, unless you hit ages (or some mental disabilities but none are relevant here) where there’s a genuine question whether they understood the wrongness – not the consequences. A six year old showing someone a photo he took of a naked peer might need a psych assessment to determine if he even knew it was wrong. A sixteen year old posting someone else’s nudes on purpose around a whole school *definitely* knows why it’s wrong.

          You also just tried to use the victimization of a child to excuse the victimization of a child – did you forget in your so-clever example that the fiance’s actions also had an underage victim, who was not only not old enough to consent but also did not attempt to give consent?

  75. JJ*

    I agree that this letter just doesn’t feel genuine, but let’s say it is for the sake of argument. Everyone is assuming the OP should break up with her fiancee, but let’s say, for the sake of argument, that she wants to stay with him (you know, maybe she deeply loves him or he is clearly a good person because he volunteers every week at the cat shelter something). Then what?
    1 Just act like the conversation with the boss never happened and never mention husband again?
    2 Ask fiancee to apologize?
    3 Move away and change jobs like the parents suggest?

    I would go with 2 if fiancee is amenable, 1 otherwise, and 3 if the coldness from the boss becomes unbearable. Honestly, I think that’s what one would do in REAL LIFE because you wouldn’t normally break up with someone you are about to marry just because of this one incident, unless there were many other problems.

    1. Lenora Rose*

      Sadly, it’s true that in real life people have stayed with partners who were found to have done something abusive and unforgiveable to someone else. heck, there’s a number of caught and imprisoned serial killers with spouses and partners, some acquired after their their imprisonment.

      I’m not sure that actually means it was always the right thing to do. Few people with such a history go on to live exemplary lives without a single further incident; far more common is the person who downplays their partner’s past history or forgives it, only to end up seeing it happen again, or become themselves the next abuse victim a few years later.

      More to the point, though, bullying the same person continually for a few years should not be downplayed as “one incident”, especially if the only one that felt appropriate to write about was nude photos. That’s less perspective and more apologism.

  76. SideshowStarlet*

    Oh, my. This is like an Alternate Universe version of the relationship between Lily and James Potter, with James as the wealthy fiancee who used to play “pranks” on his less popular classmates

  77. Lizard Lady*

    Act totally normal for now. If the relationship is truly over, feel free to say to boss “I know you are probably waiting for a request for time off at some point, since I mentioned my engagement, but that will no longer be needed.” No pointed looks or inflections, just that. If it doesn’t seem like volunteering too much, or if he asks, you can add “He turned out not to be the person I thought he was.”

  78. Purple People Greeter*

    OP, you said you had “another huge blow-up” with your fiance when you asked about his history with your boss. Please hear yourself. ANOTHER blow up. Why are you having frequent and significant fights with someone who supposedly loves you enough to want to spend forever with you? Why do you want to be with him?

    I’m not saying end the engagement yet. I am suggesting that some serious contemplation and perhaps some counseling should be high in your agenda. And if you do keep the relationship, Fiance should probably make an effort to apologize to your boss and try to make amends.

  80. Offlerite*

    How about something like: “Hi Boss, do you have five minutes? I just want to thank you for something. This is a bit awkward, but when I showed you the photo of my ex-fiance it was clear that you knew something bad about him but understandably didn’t feel able to tell me. Well, that got me thinking more about a couple of things that had seemed minor at the time and, um, long story short, we’ve split up.” Boss is unlikely to ask further questions, there’s no suggestion that OP knows anything about the bullying, and it’s established that the ex-fiance is the person at fault and that if anything Boss’s reaction was helpful to OP.

  81. Elle*

    For what it’s worth: I had something similar come up with my partner a couple years into when we were dating.

    I heard something about his past and when I asked about it he…
    1. came fully clean right away, no deflecting or downplaying
    2. he owned the full extend of it, if not more – like not only his share but what he could have done above and beyond
    3. he patinently answered all the questions I had around it and kept answering them the following couple months, because the worry and trust that was on the line isn’t a one time session thing
    4. he acknowledged in what ways he changed and what he did and is continue trying to do to be a different person in that area…

    Why am I sharing it? Because as Alison said, it’s not about what he once did but how he deals with it NOW! The fiancé is showing her, that she can’t trust him – he lied about “having no idea” what their boss could be about, that’s the biggest red fleg for me. That’s just not fair. What else is he lying about because it’s convenient?

    My partner and I both really value that we both feel and act fully responsible for our own behavior, mistakes, lives.. we own up to what we do and build trust. I don’t know if that’s possible with the financé here..

  82. Frances*

    There are reasons why you should never talk about your personal life but on the flip side it is better to know who your fiance is then to get married and have to deal with the possibility of him bullying someone else.

  83. Emily Scott*

    Hey OP. Consider this a massive red flag and call off your wedding. I don’t think your fiancé is sorry, he’s only sorry he got caught out. His treatment of your boss is beyond teenage meanness. Ask yourself how he could treat you or any of your future children. Nice men come along regularly – pick one of them.

  84. Sportsball*

    The part about the parents is what makes it way too unbelievable. The 1980s called and want their B-list romcoms and soap operas back for that plot point alone.

    If the LW wants to take that bit out, maybe they have a decent shot at submitting this to the next Poets and Writers contest.

  85. Mango Freak*

    I know we’re just getting a tiny sliver of the situation and I don’t actually know what’s going on, but I’ll just throw out there:

    I’m always made nervous by, “I have no friends who aren’t his friends.”

    Social isolation can happen a bunch of different ways, but it’s not good. If you feel stranded now, that will only get much, much worse.

  86. Tiger Snake*

    A frustrating fact that those of us who were bullied have to face is that time moves on. The people that hurt us do change. They can, and often do, become better people.
    It is frustrating and it feels unjust because we can’t move on at the same pace. Humans aren’t actually naturally good at empathy, so when we feel like we’re suffering it takes up so much space in our emotion that it shunts other things. We get stuck feeling our suffering is bigger than anyone else’s, and we get stuck feeling that recourse is necessary. We’re not naturally good at justice either, so we struggle to measure just separately to equal. We think that if we’re still suffering, they need to suffer as well; just as long, just as much as we are.

    But life doesn’t work that way. Our bullies move on. They grow, they change, they become better people and we can’t handle that idea because if they can be better people why couldn’t they be better with us. It upsets us. It frustrates us. It feels wrong and unfair. The bullies that made me miserable and suicidal and gave me crippling social anxiety are probably out there, with happy marriages and children without ever stopping to think about how the people they are now would be appalled at the people they used to be. It feels unfair to realise that they still get all that. But that doesn’t actually mean it is unfair. And that is very, very hard to face or admit.

    Boss would probably be happy to hear that LW broke up with their fiancé, because it feeds that feeling on vindictiveness. But LW doesn’t owe them any sort of explanation or closure.

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