when your teenager dates your boss’s son and it goes bad

by Alison Green on August 28, 2024

A reader writes:

I know that you’ve repeatedly discussed how romantic relationships at work can be problematic, but how do you navigate it when it’s your child? I was catching up with a friend (Sara) who told me that her teenage daughter had started dating Sara’s boss’s teenage son. Sara didn’t want to forbid the relationship as that would likely push them together even more, in a star-crossed lover kind of way. When the relationship did eventually go sour, with lots of teen angst along the way, the boss became noticeably chilly toward Sara. Obviously this shows poor management skills, but is there anything Sara could have or should have done to avoid this?

Ugh, this is really, really on Sara’s boss for letting it affect his relationship with Sara. This is teenagers dating! It’s not like their adult children got married and then one of them grievously wronged the other. It would be wrong for a manager to let that affect his treatment of an employee too, but it would least be more understandable than being this invested in a teenage romance.

I don’t know that there’s anything Sara could have done about it ahead of time. At most she could have talked to her daughter at the start of the relationship about the reality that it could intersect with Sara’s professional life — not to say “so you can’t date him,” but to say, “I trust you to operate with kindness and respect in any romantic relationship, and I’m asking you to make a particular point of that here since otherwise this could be messy” …but then she’d need to really talk through what that means (because you don’t want the daughter thinking that means she can’t break up with the guy, for example).

Frankly, though, I don’t love the idea of burdening a teenager with that. I suppose you could argue that conversation isn’t a bad lesson in the complications that come with dating someone with professional authority over a family member, but I think it’s too early for a teenager who’s still figuring out Dating 101 to have to grapple with that too.

Ultimately this is Sara’s boss’s fault, and he sucks.

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{ 161 comments }

{ 161 comments… read them below }

    1. pally*

      Just be glad boss’ son didn’t get Sara’s daughter pregnant or there’d be a whole ‘nother level of Sucky Boss to endure.

    3. Not Tom, Just Petty*

      For this reason, I think any outcome would be unpleasant.
      I’m not a chess master, but I see very little chance that boss would not have some reaction no matter what happened. If boss is so vested in son’s relationship, even saying no thanks would result in boss asking why.
      “did you ask out daughter yet?”
      “she said no”
      followed by:
      “did you ask her why?
      “she said it would be weird”
      good lord to a fly on the wall
      or “she didn’t say.”
      “well, I’m going to ask her mother.”

      just nothing good

    4. Tiger Snake*

      I think that not only is this a Your Boss Sucks situation, but it’s also a situation where Sara has to be very careful about when, to whom and what specifically she says with venting because it’s just so ripe for gossip. I think that’s unfair to Sara, but it is still true.

      For example; they say the apple doesn’t fall far from the tree, and if this is how the father reacts and how invested he is – it makes me wonder about what his son’s attitude was like and why the relationship may have gone sour. And that’s unfair, its unkind and its pure speculative gossip with no basis behind it.
      But it’s also exactly the sort of drama that people love to run with, and which Sara’s family gets stuck with labels of for no good reason.

  2. HonorBox*

    Whoa, whoa, whoa. This is far too much. I grew up in a small town and of course people’s parents knew one another. But I can’t think about any situation in which a breakup caused strife between parents. It would have had to be something particularly egregious for a cold shoulder reaction.

    These are teenagers. Teenagers date and break up. Unless Sara’s daughter threatened the boss’s son at knifepoint or something like that, this is how relationships – especially teenage relationships – go.

    The boss sucks, and if it continues, I’d suggest to Sara that she might need to find a place where the boss doesn’t act like a child.

    1. Melissa*

      That’s such a good point. My high school boyfriend was also someone in our social circle— meaning that my parents knew his parents. When we broke up (I mean when he dumped me), they still acted like regular adults to one another.

    2. urguncle*

      Seriously. It’s part of having a teenager. The most a normal person would do is say, “guess we won’t be in-laws after all” with a smile and a laugh and get on with work.

    3. Presea*

      If Sara’s daughter did something extremely egregious like that, it wouldn’t be my instinct to be chilly Sara herself unless she was defending the behavior. Otherwise I’d make sure she was aware of whatever resources and accommodations the company could offer her for dealing with whatever complex, none-of-my-beeswax situation is going on here, keep my son safe from the daughter and support his own healing, and move on civily with Sara. I feel like the boss is having a weirdly hard time seeing the teens as different people from their parents here or something.

    4. Bast*

      Small town resentments run high. I dated my high school boyfriend for two years and broke it off a few months after graduation when it became apparent we were both heading in two different directions. Obviously, feelings were hurt but frankly I feel it was to be expected. Apparently not.
      That was about 15 years ago, and as recently as last year, ex boyfriend’s mother saw my mother in the local grocery store, turned her cart around, and very pointedly headed in the opposite direction.

      1. Kimmy Schmidt*

        In my experience, small town resentments also run gendered. If the female partner does anything “unladylike”, which includes breaking up with the other partner, it’s talked about and remembered in a very different way.

        1. Justme, The OG*

          It’s like in Gilmore Girls when Luke and Lorelei broke up and the whole town wore ribbons to show which side they were on.

      3. Fitzie's chew toy*

        Years after I graduated from high school, my mother had coffee with a group of women.
        She was introduced to a newcomer and the other woman said, “I know who you are. If your daughter had accepted my son’s invitation to the prom, he wouldn’t have joined the Army and died in Vietnam.” My poor mother was speechless. The boy and I were classmates, but I knew him only to say hi AND I turned him down (graciously) because I had a steady boyfriend that I was going to prom with. So sad on so many levels.

          1. ferrina*

            Seriously. That is a massive leap. I get that the mother is grieving, but claiming that a teenager turning down a date led to her son’s death is outrageous (not to mention highly problematic).

            1. SHEILA, the co-host*

              Right? Especially since prom is one night. He easily could have still joined the army afterwards! Mom seems to have constructed an entirely alternate narrative where they fell madly in love at prom and got married immediately afterwards and started popping out kids and that would have persuaded him to stay home? Which still wouldn’t have helped her son once the draft started.

              1. Ellis Bell*

                I took that to mean that he threw his life away over a broken heart, but weren’t the soldiers for Vietnam drafted anyway? Either way, there’s some highly baked in sexism there; that women are responsible for men’s feelings and persuading them into safety and happinesses. I give her some leeway for the tragedy of losing her son, but I don’t think you can construct that mindset entirely out of grief.

                1. Orv*

                  Some were drafted, but some volunteered, too. My uncle enlisted in the Navy voluntarily because he decided he’d rather be a sailor than be drafted by the Army and sent into the infantry, for example.

        2. JSPA*

          This doesn’t make sense on any level. He could have gone to a prom and then joined the army anyway. Or not gone to prom and not joined the army. There’s no “heartbreak to army pipeline.”

          And how heartbroken can you be over someone whom you’ve barely talked to, such that you don’t know that they’ve got…a steady boyfriend?

          I mean, as a teenager, you can be in “love” with, and heartbroken over somebody that you’ve never met…but it’s all entirely inside your own head. Not something anybody else played a part in.

        1. Bruce*

          There is a common expression used to describe the feeling of having avoided a catastrophe, but I’ll only allude to it vaguely here given what happened to the guy. It is a sad story but it sure as hell is _not_your_fault_ and the grieving mom should know that.

        2. Saturday*

          I just want to make it clear that I was commenting on Bast’s story, not the very sad one.

      5. cloudy*

        They REALLY do. One time the parents of my first high school boyfriend went and complained to my dad while he was at work, because I did something they didn’t like. (My dad worked at a nonprofit and the boyfriend’s dad was on the board.)

        The something in question was that I made a post on Facebook (c. 2007) about how my parents were really cool and I appreciated how chill they were, which for some reason my boyfriend’s mom thought was supposed to be a passive aggressive dig at her because she wasn’t included?

        My dad made me write an apology letter for it! Probably because he didn’t want to hear about it anymore.

        1. Radioactive Cyborg Llama*

          Amused at the irony of your father making you apologize for saying he was cool.

          1. cloudy*

            The whole situation is kind of funny in hindsight. I don’t think he agreed that I’d done something wrong, but my guess is that he was treating this as a life lesson in interpersonal politics and knowing how to smooth things over even if isn’t wholly fair.

            Though I think at age 16 my bigger takeaway was not to add your boyfriend’s parents on Facebook.

      7. NotJane*

        So true! When I was a freshman in high school, I dated a guy who was the “popular” older guy in our church youth group. Another girl in the group had a huge crush on him so she decided that I was her mortal enemy and wouldn’t speak to me after he and I got together. I then saw her at a high school reunion (I think it was our 25th) and said hi because I honestly had forgotten about all the drama. She literally turned her back on me. Girl, he wasn’t worth all that for sure!

        1. allathian*

          Some people peak in high school and get stuck there for life. I guess she hadn’t been very lucky in love after graduation, either. I didn’t date in high school (far too shy and awkward and not popular with the guys), but I barely remember the crushes I had then… Oh well, I’m coming up on my 35th anniversary, so…

    5. Hannah Lee*

      Wasn’t there a previous AAM LW who ran into issues with a new co-worker, who turned out to be the parent of LW’s child’s ex and had acted out to the point that she wound up with a restraining order against her?

      Sometimes people are just OTT jerks, kids or no.

      1. Bruce*

        I also remember one where the new employee was the parent of a kid who had bullied the letter writer’s kid, that one was a roller coaster that had a satisfactory ending…

        1. Hlao-roo*

          The letter Bruce is referencing is “my new employee is the parent of my child’s bully” from June 27, 2023 (and an update June 4, 2024) for anyone curious.

    6. Golden French Fry*

      People get so weird about this stuff. I’m pretty sure I obliterated a years-long, across state lines family friendship by just dating a guy at my high school.

      I think the other family had a daughter that liked stringing my ex along as far as if they would ever date, but he lost interest in that and started dating me. All the adults got weird and I think things blew up over it after a positive comment my ex’s dad made about me. I didn’t have anything to do with it, the other family lived in another state and I think I maybe met them once?

      As far as I can tell from important events on Facebook, the relationship between the families doesn’t seem to have recovered to the closeness they used to be.

    7. Jake*

      Your experience in a small town was much better than mine. I’ve never experienced a more cliquey and immature group of people than the people in my hometown that were my parents’ age range.

      1. Orv*

        Small towns are the worst in terms of people being judgy. And you can’t necessarily just get a different job because often there are no other jobs.

    8. Cat Lover*

      I don’t live in a small town- but my high school boyfriend and I went to two different high schools, but his mom was a teacher at my high school. Really awkward when I broke up with him. She was never my teacher but I would see her around.

      1. Anon for this*

        I had a classmate in high school in that situation. He and his girlfriend drove to another town to buy condoms, so no-one who knew his mom would find out. We weren’t living in a particularly small town either.

      2. Deejay*

        I used to know someone like that and they said it was hell because in any interaction with their parent at school, the parent would make a big show of treating them as harshly as possible to avoid any chance of accusations of favouritism.

    10. DisgruntledPelican*

      I remember a girl who lived down the street from me broke up with her highschool boyfriend a few months after graduation and neither her mother nor the boyfriends mom ever got over it. Like they grieved together like someone had died. The girl was eventually disowner by her parents when she started dating someone new, but considering she’s been married to that new boy for the last fifteen years, I think she came out ahead.

  3. Yup*

    Ugh, poor kids! This is what happens when teens date. They aren’t mini adults, they are learning and failing and breaking hearts and picking themselves up and starting again. It’s normal. It’s necessary! That boss does suck. They should be talking about how to help their kids navigate this, not having boss act like a teenager, too!

  4. Ally McBeal*

    I went to a very small, private, Christian church-school for grades 9-12, but it was a K-12 school. I graduated with around 50 people. When I say everyone knew everyone’s business, I mean it. At one point the music minister’s son started dating the 3rd grade teacher’s daughter, and everything was fine until they broke up and the TEACHERS started taking sides. I went to a huge university in an attempt to escape that small-town dynamic and it took me a good 4 months to realize that most people in a normal environment don’t actually care about your personal business.

    1. ScruffyInternHerder*

      So on my initial read here, oof. I mis-read that the music minister and the 3rd grade teacher were dating, and the teachers were choosing sides. And I thought that THAT was shitty.

      1. Ally McBeal*

        To my knowledge, no faculty members at that school were dating each other, although we had a few married couples. However, we did also have a scandal right before I started where the headmaster and the French teacher had “an inappropriate relationship” (which at that school could be a full-fledged affair or just the appearance of impropriety) and both had to resign.

      2. Arrietty*

        My school had a drama along these lines but worse – two teachers were having an affair, her husband (also a teacher at our school) found out (as did everyone else), and as I remember it, at least two of them left. I don’t recall which two.

      3. allathian*

        I went to a combined junior high/high school, the only school for my linguistic minority (Swedish) in a mid-size city (pop. 150k in 1990, now 250k) in Finland, although it counts as large by Finnish standards. The schools had about 500 students and 40-50 teachers. Many teachers worked at both schools that had different principals.

        The high school principal was married to the junior high secretary. The high school secretary was the mom of one of my classmates, who pretty much only saw his mom at school because he had a troubled relationship with his dad, and lived with his best friend’s family until he graduated high school. I only learned about this at our 15th anniversary class reunion because they kept it quiet at the time and I wasn’t friends with either of them (although I did have crushes on both of them!).

        One of the high school English teachers, who didn’t teach in junior high, married the junior high principal. That didn’t stop him from trying to look up the skirts of the popular/pretty girls, some of whom took their revenge by openly flirting with him in class to get better grades, and they actually did get better grades. This was possible in the 80s, but now a teacher like that would be investigated (kids have phones with cameras!) and fired.

        The high school science teacher was also married to a junior high teacher, and the junior high science teacher had been my dad’s friend since their undergrad days (my dad’s a retired scientist). Thankfully he was professional and never asked me how my dad was doing, for example.

        The school had a weird small town vibe in my mid-size city. It’s not for nothing that the Swedish-speaking community in Finland is called the Duck Pond because there are such weird connections between people.

    2. ferrina*

      Small schools are full of petty drama. I started out in a small school, then moved to a much bigger school. It was such a relief when not everyone knew my business, and there were people who didn’t know (or care) who I was.

    3. Jake*

      That was the best part of going to a huge university for me! Holy Cow! Nobody cares about the fact that my mother cleans their uncle’s house, or that my dad arrested their cousin!

      It convinced me that living in a small town wasn’t in my future.

    4. Orv*

      That tracked with my experience living in a small town. We moved right before my 6th grade year and I was an outcast until I graduated. Everyone already had their cliques and I couldn’t break into any of them.

  5. Keyboard Cowboy*

    Simultaneously “wow this boss sucks” and really really wanting to know what happened with the kids and in what specific ways the boss sucks. I guess I’m gossip-starved today.

    1. Nonanon*

      RIGHT, the gasp I let out only for LW to not provide any details!
      (Which is of course within their rights but also… I’m so gossip-starved)

    2. Double A*

      Ha, I was feeling that the other day with the letter about how people were coming up to the LW wanting the gossip about a firing. Like, clearly you should not tell your coworkers, but can you please include details in your letter because I want the hot gos too.

    3. Antilles*

      Unfortunately, I suspect the most likely answer here is also the most boring:
      What happened with the kids is plain vanilla minor high school bullcrap the kind of stuff that seems super important in the moment but even the people involved look back a few years later and go “oh right that was so pointless, hard to believe we ever cared about that”.

      1. a clockwork lemon*

        When I was in high school one of my mom’s friends was PROFOUNDLY upset when I broke up with a guy I was dating who was, like, casual friends with her son’s then-girlfriend or something like that? She had somehow gotten it in her head that I would (or maybe should?) marry this “nice boy” and I remember my mom straight-up laughing in her friend’s face at the suggestion.

        If I remember correctly, I broke up with him because he decided to take someone else to prom instead of me after I’d already bought a dress. I remember nothing else about the boy and have no idea what happened to him after I broke up with him, but I still have and wear the dress!

        2. Greg*

          Not to nitpick a great story, but if he asked someone else to prom, wasn’t that him breaking up with you? Hard to imagine taking one girl to prom but still considering a different girl as your girlfriend

    4. Today’s LW*

      Letter Writer here! Sorry I don’t have the good gossip! We didn’t get into too many details, but it sounded like normal kid stuff. There seemed to be tears, a few friends picking sides, and a couple of passive aggressive social media posts – normal teen heartbreak.

  6. Dandylions*

    Does the boss suck?

    For all we know Sarah’s daughter assaulted her bosses son … there is really no way to know. And what specifically is noticably chilly in this context? I can see this being problematic or fine depending on what OP meant.

    OP you have one moms side of one teens side of what could be anything from run of the mill teenage dating drama to something truly atrocious and nefarious. As a woman myself I witnessed more then one fellow girl in highschool do some terrible things to their exes that had real life altering consequences. Not to mention if you gender swapped to be more anonymous and an SA situation could be easily on the table (not that it doesn’t happen the other way around just much rarer). We don’t know what this situation is so I think depending on what chilly behaviors are being exhibited that this could be a completely appropriate and professional response.

    1. kalli*

      IF we write fanfic about all the letters we can make the right advice be whatever we want, especially when it’s one of the many hypothetical or ‘my friend’s cousin’s dogwalker’s nonna’s sewing circle friend’s kid’ letters that is so incomplete it can only be treated as a general hypothetical where the advice is applied to the most common denominator.

      But in 99.95% of cases two people who are not dating should not be impacted by whether two people who happen to share genetics with one or both of them are or are not dating. The most professional response is not “chilly”, it’s ‘behave professionally, which should resemble how you were behaving before because we expect everyone to behave professionally’.

      That’s it. That’s all there is.

    2. The Unspeakable Queen Lisa*

      Good grief. Stop with the fantasy writing. For all we know, you’re secretly an alien trying to foment unrest between humans to make it easier to conquer Earth.

      Go write some fiction somewhere else.

      2. Eh...*

        Counterpoint, noticing reactions might be different if genders were swapped reactions is not wrong.

        Also, there’s lots of fanfic here.

        2. lunchtime caller*

          They didn’t just say “what if the genders were swapped” they said “what if the LW swapped the genders writing in and the friend’s son SA’d the boss’s daughter” which is a COMPLETELY different letter and obviously a CRIME

    3. Lyssa*

      If boss is just being chilly, not actively mean or rude, I suspect this is more a issue of awkwardness and uncertainty about how she feels about it than sucking. Often, when people aren’t sure what to say or if another person has negative feelings toward them, they just withdraw. Not ideal, but I don’t think it rises to the level of sucks. Probably the best thing would have been for either/both to head it off by being up front when things started about the fact that we all know teen romances are usually ill-fated, and know that everyone expects these crazy kids will eventually break up and hate each other.

      1. Figaro*

        “Often, when people aren’t sure what to say or if another person has negative feelings toward them, they just withdraw. Not ideal, but I don’t think it rises to the level of sucks.”

        I completely disagree. If you’re a manager and you do this to your employee, yes, you suck as a manager.

        And I don’t agree they should have “headed it off” by talking about it from the start, because how could the employee possibly expect her manager to be so immature and unprofessional about it? They need to be less involved in their dating teenagers, not more.

    4. HonorBox*

      I have to believe that OP would have given details if it was something really awful that happened between the teens. But let’s play out the idea that Sara’s daughter did something terrible that caused the breakup for a second…and I’m thinking cheating or something like that. Unless it is something that requires some sort of legal response, a parent has to be able to draw a distinction between their response to, and support for, their child and their workplace interactions. If the interaction between boss and Sara has changed even one bit in light of the breakup, that’s crappy behavior. This is something between the teens, not between the parents.

        1. HonorBox*

          But if you’re friends with Sara and writing into a site like this, you’d know and share details because “is the boss being weird and crappy” is not a question that can be answered well if details are omitted.

          1. Dandylions*

            I mean… all the details were omitted. Noticably chilly could be as benign as not saying hi each morning to blocking her from projects. One is problematic the other not so much IMO.

            1. Your Former Password Resetter*

              Can we all please stop cross-examining every potential detail of a letter just in case it hides some massive soap opera twist that dramatically turns the entire letter on its head?

              It’s a fallout between dating teenagers, not an episode of a murder detective show.

              1. Insufficient Sausage Explainer*

                I cannot commend your last sentence highly enough.

                Some bad cases of podcast brain in the replies here…

    5. Not on board*

      I would think that if it was something serious like an assault, the OP would have said something.

      You’re also assuming that the OP isn’t able to asses a change in the boss’s behaviour towards the OP that coincides with the teenage breakup. The boss behaving any differently towards OP based on the teenagers breaking up is NOT OK, and it’s a little disturbing that you jump right to the teenage girl assaulting the now ex-boyfriend especially since it’s the other way around. – it’s also disturbing that you think it’s ok to now treat OP differently based on something her daughter may/may not have done.

      2. HonorBox*

        Also citing instances in which an ex did terrible things doesn’t add up here. They broke up. There’s nothing in the letter that indicates the daughter is doing anything else.

    6. Irish Teacher.*

      Even if Sara’s daughter did assault the boss’s son, that is a problem with the daughter and not with Sara. Yes, I would have more sympathy with the boss in that case, as it would be awkward working with a relative of your son’s abuser, but his reaction would still be wrong. Sara is not her daughter.

    7. Elle*

      Even if this writing exercise were true, it’s still not accurate to say that’s the boss’s behavior is appropriate. If something truly untoward happened with the kids, the appropriate way to handle that would be to, y’know, handle it- not just start being cold to your employee, and say nothing about it.

    8. ferrina*

      I agree with all the previous comments warning of the dangers of fanfic.

      If there was something bigger going on, it would be appropriate for the boss to go to HR and have a conversation about how to move forward. There was another letter about a parent who was supposed to manage the parent of her child’s bully where it was a severe situation- Alison’s advice there covers what you’re talking about.
      Here’s that letter: https://www.askamanager.org/2023/06/my-new-employee-is-the-parent-of-my-childs-bully.html

    10. Radioactive Cyborg Llama*

      “more then one fellow girl in highschool do some terrible things to their exes that had real life altering consequences.”

      I’m skeptical of this statement. It sounds so much like the bogus “One accusation could ruin his life!” thing you hear from men who think that complimenting someone’s skirt is (a) going to get them canceled and (b) a really confusing gray area.

      1. sparkle emoji*

        Yeah, this was bothering me too. How many things are the teen girls doing that would truly have life altering consequences? The list I can imagine is pretty short, and none of the potential bad acts are exclusive to teen girls.

      2. Dandylions*

        Eww no.

        I was actually one of the people who got that terrible “affairs at work” claiming just such a thing occured at sea taken down for this very accusation.

        Honestly I was just thinking that OP is hearing everything 3rd hand from a biased source and assuming it’s just teen angst was a bit dismissive. I witnessed some nasty things in highschool from boys and girls alike, mostly boys, but it was all pretty serious.

    11. sparkle emoji*

      As someone who was the victim of SA at the hands of a high school partner, this still wouldn’t be justified. Parents don’t typically have that much control over their teens– I’d think a person was a loon if they blamed what happened to me on my then-partner’s mom, she was a great lady who did nothing wrong– and even if you do blame the parent, the consequences shouldn’t happen at work.

    12. GenX, PhD, Enters the Chat*

      Why, hello, fellow woman! I too have seen my fellow, same-sex-as-me girls be mean to people.

    13. Green Post-Its*

      Good grief, this is like those people who read a recipe and say, ‘I changed everything and it was disgusting, zero stars’.

      Of course if you invent terrible situations, that would indeed be terrible, but it has NOTHING to do with the meagre facts outlined in the original letter.

      (Frankly, I also wish that this kind of second-hand ‘my friend’ question wasn’t published – there’s just too little information to fully give useful advice.)

    14. jasmine*

      I know we want to avoid fanfic, but to be honest, this was my thought. The boss’ reaction is so strange that it’s equally likely that the boss is unreasonable or that one teen did something horrible to the other). I’m not sure it’s fanfic to say that

      1. Banana Pyjamas*

        It’s not fanfic to say it how you said it, but it’s fanfic to outline what may have happened. Ferrina had a great comment above that linked to a pertinent situation if something terrible DID happen.

        1. Dandylions*

          Thank you this was helpful.

          One thing I struggle with is explaining my why before I just say my thoughts. I’ve been working on it. It often causes problems and this is just another example.

          The fanfic responses flabbergasted me but you explained why it’s coming across that way succinctly and I appreciate it.

    15. Hyaline*

      I feel like the “but what if” “no fanfic” “but we don’t know” cycle on this one really illustrates the limitations of secondhand information on this, and it’s helpful to remember that the root of the question isn’t “dish on this particular boss” but “what, if any, are the parameters for mitigating teenagers’ dating lives on adult parents’ professional lives.” Barring very extreme cases, the answer remains “the adults should just continue acting like adults.”

    16. Ellis Bell*

      In this completely made up thought exercise, did Sara hold him down while her daughter assaulted him? Or, after deciding to stay out of her daughter’s business, have anything at all to do with any of it? Because unless Sara herself personally did something, I’m still not seeing why she’s getting side eye from the boss.

    17. Today’s LW*

      I think you’re really reaching here. From what Sara told me, it was a normal teen breakup. It’s possible that it was a lot more ugly, and Sara doesn’t know or didn’t share the details, but I think it’s highly unlikely. I mentioned this in another comment, but Sara and her boss used to chat regularly, and now the boss will only greet her if Sara says hi first. There’s no longer any small talk. Sara is also having an issue with get supply orders approved in a timely manner, but none of her colleagues are having the same issue.

      1. allathian*

        Can Sara talk to her grandboss or HR? The cold shoulder is bad enough, but this is affecting her ability to do her job properly. At least a CYA for performance evaluations, like Sara’s boss penalizing Sara for failing to meet expectations when she’s the biggest hurdle.

        1. Today’s LW*

          Possibly. Sara is concerned about the plausible deniability in the situation. She’s in education – budgets are always tight, and it’s not uncommon for supply orders to be cancelled or delayed. I think she’s decided on a “wait and see” approach, but that may change.

    18. 2cents*

      From the commenting rules, and adding a link here so that it goes through moderation and Alison sees it: https://www.askamanager.org/how-to-comment

      3. Limit speculation on facts not presented by letter-writers to reasonable assumptions based on the information provided.
      • Don’t invent possibilities simply because you could imagine them to be within the remote realm of plausibility.
      • If you’re speculating on facts not in the letter, explain how it’s actionable for the letter-writer. “She might be stealing your lunch because she can’t afford her own” is not actionable (and quickly becomes derailing). “She might be stealing your lunch because she can’t afford her own, and so you could try X” is actionable.
      • Do not accuse people in the letter of nefarious motives based purely on speculation. Letter writers aren’t characters in a story; they’re real people.

  7. HannahS*

    Oooh that’s rough. I realize that parental relationships are all different, and not all teens are the same (obviously!) but when I was a teen, my mom (who worked with private medical information) sat me down and said, “Look, I know a lot of things about a lot of people, and obviously I can’t share private information with you. But if I ever tell you that you CANNOT date a certain person and don’t elaborate, it means that I know something about them that means that you really shouldn’t date them.” I felt respected and was fine abiding by that.

    It never came up (because I didn’t start dating until I was in my 20s and living in a different city, womp womp) but it was a good way of handling it. It seems like Sara knew that explaining to her daughter why it was a bad idea wouldn’t have worked, which is too bad.

    1. JustKnope*

      I still think this would have been an inappropriate use of your mom’s access to private medical information, unfortunately.

      1. Pocket Mouse*

        Big same. She should have provided a bunch of info and insights about healthy sexuality, STIs, birth control options, dating violence, and trust, and left it at that. It’s enough of a violation to say (or insinuate) “So-And-So is a patient at this practice” regardless of what their medical records say.

    2. old song memories*

      Reminds me of that song (from Newfoundland? heard it from a Newfoundland group, but can’t remember which one). About a girl who wants to date a boy in her small town, and the dad says “no you can’t date him, he’s your half-brother”, and it keeps going in rounds till all the boys are eliminated. Then the mum says “date whoever you want, your dad is not really your dad”.

    1. JustaTech*

      Seriously. By the time your kids are teens you need to learn how to pull back from their lives so they can stand on their own.

      Two relevant stories: Two of my good friends from high school dated while they were in college, two separate times (yeah, not great, but that was on them). After the second time they broke up, one of them was taking a Master’s level course where the other person’s dad was the professor. On the first day of class he said “You know, you’re not allowed to teach your own children because it’s a conflict of interest, but it’s perfectly fine to teach your child’s ex.” Both of my friends were mortified (one because they’d just been called out by a professor, though thankfully not by name) and the other because their dad had just been a huge and pointless jerk in class (ie, at work).
      The dad was 100% in the wrong, and was called out by his kid for it (“don’t fight my battles for me, dad, especially ones that I’m not fighting! We’re cool! I don’t hate [ex]!”).

      Second story: I went to private elementary school with a girl who’s dad was a Big Deal CEO in our city, and was the boss of about a lot of the parents in our class (but not mine). On of my friends was told by her dad (in second grade!) “you need to be nice to [Big Deal’s daughter] or her daddy might fire Daddy.”
      Which is a totally unreasonable thing to say to a child (not to mention to threaten your employees with), so both dads were being unreasonable (though given his later behavior I can actually believe that CEO guy would have said that).

      All of which is to say, you shouldn’t bring your kid’s social relationships into work if you can avoid it, it’s unproductive and unprofessional.
      (The bullying example from a while back is an obvious type of exception.)

  9. Tesuji*

    I mean, it’s *probably* the boss being an AH, but I feel like a secondhand story like this could encompass a lot of possibilities, which are probably worth considering.

    What was the status quo ante? If the boss went from ‘professional’ to ‘icing Sara out’, that feels indefensible in any reasonable scenario… but what about if this was an ‘we’re all friends here!’ kind of place? If ‘chilly’ means a normal professional relationship, downgraded from a ‘Sara’s family used to get invited over to the boss’ house for BBQs, which is where the kids met’, I’m kind of okay with the boss taking a step back.

    What actually happened in the relationship? There’s possibilities that I could reasonably see reflecting on Sara herself, in a “Wow, if that’s how she’s raising that kid, maybe I need to reevaluate my opinion of her” kind of way, like assault or spreading lies with life-changing consequences.

    … and, yeah, those scenarios are kind of speculative, but then again, so is “I choose to believe that this is just normal teenaged drama and nothing else!” when even the original LW doesn’t seem to know the details.

    1. Pay no attention...*

      This is where I’m landing too. If the boss used to discuss family with the mom, and now refuses to discuss the kids’ or his family business at all, that’s somewhat expected.

    2. Irish Teacher.*

      What actually happened in the relationship? There’s possibilities that I could reasonably see reflecting on Sara herself, in a “Wow, if that’s how she’s raising that kid, maybe I need to reevaluate my opinion of her” kind of way, like assault or spreading lies with life-changing consequences.

      Honestly, while I can understand the boss having that reaction in such situations, I think it would still be unreasonable. Children aren’t blank slates for the parent to mould as they choose. I have had some students who behave terribly and as far as I can see, their parents are doing everything right as regards dealing with the behaviour. There are all kinds of reasons teens act out. Poor parenting is one, but trauma is another (we had a student who started acting out after he was mugged, something completely beyond his parents’ control). Influences other than the family can also play a part, as can things like disorders that affect impulse control or addictions…

      To completely change one’s opinion of somebody because they have a kid with behavioural problems is not a reasonable response in my opinion.

      And with the lies, I think one would want to be very careful, unless there is very strong evidence it is a lie because it’s easy to assume “my child wouldn’t do that. The kid who accused him/her of it must be lying” and I would say more often than not, that is not the case. But even if it was conclusively proven, it doesn’t necessarily reflect on the teenager’s parents. Teens lie for a lot of reasons, often either fear (like she was assaulted by somebody else and said her boyfriend did it because she was so scared of the actual abuser) or because they don’t realise how serious the consequences could be. It’s rarely something their parents are to blame for.

      Unless Sara actively participated in harming the boss’s son, like say he broke up with her daughter and she started harrassing him, accusing him of cheating and insisting he apologise to her daughter, then the boss is in the wrong.

      1. Radioactive Cyborg Llama*

        Similar to what I said earlier but I do wish people would stop indulging in the “life changing consequences” fiction. Actual rapists don’t even get life changing consequences, unless you count getting appointed to the Supreme Court.

        1. Irish Teacher.*

          Yes, I agree. I would really be giving the side eye to a boss who started being chilly with their employee because “her daughter lied about my son and it led to life-changing consequences.” A parent insisting their kid is innocent and was lied about…isn’t exactly the most reliable judge of the situation.

      2. ferrina*

        Totally agree with this. Parents shouldn’t be held accountable for their children’s relationships unless there is evidence that the parents were involved.

        My mom didn’t know half the things I did or said with my childhood friendships/romances. I didn’t tell her most things, either because I forgot or I was embarrassed (whether I deserved to be or not) or I didn’t think it was important or I thought it was so important that I didn’t want to tell my mom.

        My mom’s approach to this was to apologize to all my friends’ parents, because she assumed that something had happened and whatever it was it was probably my fault (I had undiagnosed ADHD, so her assumption that everything was my fault was based partially on probability- I was highly impulsive- and partially on ablism). This boss would probably have no problem with my mom. That said, I don’t recommend this approach to parenting- assuming your child is to blame for everything is not a great way to maintain a healthy relationship.

      3. Ellis Bell*

        Completely agree with you that kids aren’t little mirrors displaying exact replicas of the behaviour codes their parents programmed into them
        People who think: “Wow, if that’s how she’s raising that kid, maybe I need to reevaluate my opinion of her” are simply people who know very little about teenagers.

    3. Radioactive Cyborg Llama*

      “spreading lies with life-changing consequences”

      This is almost 100% fiction and I wish people wouldn’t act like men are in so much danger from it.

    4. r..*

      Children are separate people, not extensions of their parents, and sometimes they choose to do stupid things despite the best of their parent’s intentions. Especially during their teenage years. There’s no magical “stop being stupid, child” switch parents have access to, and could be blamed for not pushing.

      We have had employees whose children ended up using drugs, or being committed of a crime, despite their parents best intentions.
      We have had employees whose children turned out exemplary in a way I am reasonably certain was not brought about by exemplary parenting.
      Conversely we also had employees who are amazing, yet were born into … difficult circumstances.

      I am not going to judge people by who their parents were, and I am not going to judge people by how their children turn out to be.

    5. Figaro*

      “If ‘chilly’ means a normal professional relationship, downgraded from a ‘Sara’s family used to get invited over to the boss’ house for BBQs, which is where the kids met’, I’m kind of okay with the boss taking a step back.”

      No, if you’re treating the employee differently and outside what is considered normal behaviour at your workplace, treating them differently from other employees/colleagues, because of something you believe their teenage kid may possibly have done, that is appalling.

    6. Dandylions*

      Technically third hand. OP heard from Sarah who presumably heard it from her teen daughter.

      This is where I landed but over explained and caused more trouble lol.

      Basically this is third hand, not sure what chilly means, this may be a huge problem or a nothing burger of momentary awkwardness. Hoping for Sarah it’s a nothing burger.

    7. Today’s LW*

      Sara told me that she and her boss would greet each other and chat for a few minutes when they ran into each other, but now the boss only greets Sara if Sara says hi first, and won’t engage in small talk. There’s also been some delay in supply requests that the boss has to approve. Sara is in education (so her boss can plausibly claim that the budget is tight) but none of Sara’s colleagues are experiencing the same delay in getting supplies.

  10. Trying Out a New Username*

    I think that the boss had a responsibility to have the conversation with their son that Alison suggests Sara could have had with her daughter. Yes, this puts an extra burden on a teenager for being the child of a manager, but it’s a necessary one that neither Sara nor her daughter should carry.

    1. HonorBox*

      That’s a really good point. Management carries greater responsibility, and while it isn’t necessarily incumbent upon the family to carry the same responsibility, this seems like a spot where parent’s working relationship with employee might need to supersede child’s romantic desire.

      Putting the responsibility for that conversation on Sara also opens up the possibility that boss hears that Sara told her daughter she can’t date boss’s son which could make things awkward too. Boss can smooth it over better by saying something like, “I just didn’t want things to get weird here because we both know kids break up…”

    2. Hyaline*

      I think the point of having a conversation with either child isn’t to put additional burden on them or to set “you can’t date” parameters, but to help them understand the complexities, nuances, and interconnectedness of the big wide world. As a parent, I wouldn’t consider having a conversation like this with my kid to be “burdening” them, but equipping them and giving them a real-time lesson in How the Real World Works.

  11. East Coast Commenter*

    This all feels so dependent on what “chilly” means. I don’t think it would be horribly unprofessional for the lingering awkwardness to lead the boss to draw back a bit, particularly if the chilliness is not protracted.

    1. Today’s LW*

      I posted this above as well – Sara told me that she and her boss would greet each other and chat for a few minutes when they ran into each other, but now the boss only greets Sara if Sara says hi first, and won’t engage in small talk. There’s also been some delay in supply requests that the boss has to approve. Sara is in education (so her boss can plausibly claim that the budget is tight) but none of Sara’s colleagues are experiencing the same delay in getting supplies.

  12. Not A Stripper*

    Not to be a turd, but I don’t think the original poster ever noted that the boss was a man. Could just have easily have been a woman. I realize this isn’t the point of the post, though.

    1. Lily Rowan*

      No, I clocked that too! Especially since we know Alison defaults to assuming anyone is female!

      1. Arrietty*

        Alison doesn’t default to assuming everyone is female, and has said in the past that she will use pronouns in a way that makes her answer clearest if there’s no indication of gender. If the boss were female, this answer would have a lot of shes doing things to hers and it wouldn’t be easy to follow who was who.

  13. NobodyHasTimeForThis*

    As a move forward scenario, it really sounds like Sara needs to just talk with the boss.

  14. Apex Mountain*

    It seems highly likely that the boss just sucks, but with second/third hand letters like this the OP (and therefore us) just don’t know all the information

    2. Baroness Schraeder*

      I noticed this too! Not because it makes a difference, but because Alison usually assumes bosses are female unless otherwise specified. The reference to “him” in the reply caught me by surprise.

  16. s*

    Just give it a couple of weeks, Teenagers have a looooot of emotions. Both parents are dealing with the fallout at home and of course there will probably be some awkwardness. Also both parents probably know more about the other’s families than they would otherwise and there has to be some selective ignorance going forward.

  17. BananasInPyjamas*

    Is there a reason we’re assuming the boss is a man? I know Alison refers to them with he/him pronouns, but the letter writer themselves never specify. Wondering if the letter has been edited down.

    (It’s a really small point and it doesn’t take away from how much the boss sucks, I’m just interested in how Alison reached the conclusion the boss is a man)

    1. Today’s LW*

      The boss is female. I’m pretty sure Alison posted it exactly as I sent it, but I didn’t check word for word.

  18. Czech Mate*

    When I was a teenager, I dated the eldest son of one of only two orthopedic surgeons in town. Relationship went VERY south, as teen romance often does. In solidarity, when my mom needed a knee replacement, she went to the OTHER orthopedic surgeon in town. Other orthopedic surgeon turned out to be an a$$. (Like, he came in and said, “Wanna know how I know you don’t have cancer?” My mom said, “Um, could it be because I’m here to see you about my knee?”) She eventually went to go see the father of my ex, but very, very grudgingly.

    He was fantastic. Extremely kind, extremely professional. Acknowledged that they knew each other, but didn’t bring up the teen relationship at all. The guy was not perfect in many ways, but I will forever be grateful to him for how he treated my mom when she was in pain and needed help.

    1. Irish Teacher.*

      Somehow I read this as “I dated the eldest son of the only two orthopedic surgeons in town” and assumed they were married and both his parents.

    2. allathian*

      Teenage dating is probably different but my parents never met the parents of my first serious boyfriend (I was 23 when I met him and 25 when I left him) even if I met his parents and he met mine.

  19. A Simple Narwhal*

    Geez, I know my mom has kept a running list Arya-style of every person who has wronged me in my childhood (from the random lady who yelled at me and made me cry after a soccer game when I was 5 to the other coach who scoffed at me as a teenager when I passed a sports certification to advance a level and told me I was lucky and unlikely to pass another one ever again) so I can understand the boss having Feelings, but part of being the boss means not letting that affect your professional relationships, especially for someone you manage.

    I also suppose it depends on what “noticeably chilly” actually means. If they’re just not as overly personable but are still professional and cordial that’s way different from actively ignoring them or being rude or treating them different from their colleagues.

    1. allathian*

      The LW posted elsewhere about this. I’m paraphrasing but basically the boss never greets Sara unless she greets her first, never talks about anything other than work, and causes unnecessary delays in things that need her approval when they’re given by Sara but not the other reports.

    1. Jessen*

      Definitely. I’d have different advice here depending on if we’re talking about 13 or 17. The older you get I think the more equipped they are to understand that relationships are messy and sometimes you have to worry about the consequences for other people. Even if it’s not fair.

  21. Radiolarion*

    Re: number 20: I have a Gen Z direct report who always wears crop tops and I’ve assumed that commenting on that choice would be more unprofessional than her choice to wear the tops to begin with! We work in a casual academic environment where there isn’t a dress code rule I could point to to police the choice. I’ve wondered whether it’d be a kindness to point out that others might see it as unprofessional, but it also feels too close to commenting on her body at work.

  22. nnn*

    What struck me about “I trust you to operate with kindness and respect in any romantic relationship, and I’m asking you to make a particular point of that here since otherwise this could be messy” is the relationship could still have problems for reasons outside the scope of the employee’s kid being kind and respectful. Or, even if the employee’s kid is kind and respectful, the boss’s kid could portray it otherwise.

    The example that keeps coming to mind is one from my own adolescence, when a classmate’s stated reason for breaking up with another classmate was “She’s completely psycho!” when what he actually meant was “She cries during movies and it makes me uncomfortable to be in the presence of freely-expressed emotions.”

    If I were advising both Sara and her boss, I’d advise them to behave in the workplace as though their kids were small children having a child-sized disagreement because big feelings are involved. If they were, like, 2 years old and disagreeing over a toy in the sandbox, you’d be like “Aww, poor kids! Big feelings! Anyway, TPS reports!” That’s the kind of energy to bring into this in the workplace.

    (Obviously, I don’t advocate for treating the actual teens as small children and trivializing their emotions like that to their faces, it’s just a thought experiment to arrive at the right tone in the workplace.)

    But I can’t think of anything Sara can do single-handedly if the boss isn’t onside with making this work as well.

  23. Figaro*

    With some teens, you could probably have a conversation about this, but with others, it would be a terrible idea. It might add to the allure of the relationship! They might run off to the other kid and say “your mum might fire my mum if you’re not nice to me!” They might think it’s funny to stir up trouble!

    Teenagers have varying levels of maturity, compassion, comprehension skills etc…

  24. Greg*

    I agree with Alison that the boss sucks, but I also think it would have been a good idea for Sara to be more proactive in speaking to him. Not in the sense of a formal conversation, just saying something at the outset to establish that they’re both on the same Concerned Parents team, and that if the inevitable teen drama happens, they won’t let that affect their work relationship. And then, immediately after the breakup, something along the lines of, “Hey, sounds like it didn’t work out between Buffy and Angel. He’s a great kid and I really enjoyed getting to know him. Give him my best!”

    (And yes, the boss should have done the same thing. But in this narrow sense, they are peers, so there’s no reason Sara couldn’t have raised the subject.)

  25. rebelwithmouseyhair*

    I’m wondering what the teenage son said to his dad to make him chilly towards the girl. I mean, we don’t have any details about the circumstances of the breakup but if the boy was in the wrong we can be sure he didn’t tell his Dad exactly what happened.

  26. Lizzo*

    #52 – I have been egged before, and the eggs were traveling with similar velocity as they might have if they were dropped from one floor above. It hurts like hell. Please don’t hesitate to show this guy out.

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