updates: my boss is having an affair with his assistant, and more

by Alison Green on June 22, 2022

It’s a special “where are you now?” season at Ask a Manager and I’m running updates from people who had their letters here answered in the past. Here are four updates from past letter-writers.

1. My boss is having an affair with our assistant — and I’m friends with his wife

I tried to keep under the radar at work as much as possible and continued plugging away at my job search while trying to ignore whatever was happening with Tammy and John.

The affair eventually came out. John was poorly covering his tracks at home and my friend/his wife eventually figured out something was going on. They have now separated and are going through a very contentious divorce. John and Tammy are openly a couple now and are expecting a baby this summer.

My friend was understandably devastated, but she did not ask me if I knew or if I suspected anything. She told our hobby group who has rallied around her with support.

I am happy to report that I accepted a new position a few months ago and am now working in a similar position with a different organization. The new company is larger and much better managed, and my new boss communicates transparently and views hiring as a process for meeting business needs rather than doing personal favours for people! It is such a relief. I do not know anyone here personally, and have resolved not to mix friendships and business again in future, if I can avoid it!

2. Can my remote job make me visit the office at my own expense? (#3 at the link)

Luckily, I’ve never been asked to join any in-person meetings or events. There have been a few friendly invitations to use local coworker’s guest rooms for casual get-togethers for our social media pages, but I’ve only replied gratefully but noncommittally. When they say “all hands on deck” they’re also very careful to say “for everyone who lives local to the area” and “please come help if you can.”

Seems like a raw deal for anyone who lives locally to always get roped in to get the dirty work done, but I at least try to offer to do extra admin/email work to help cover their days spent away from their regular work. There are a number of full-time remote team members now, including several that are high-up in the company. The bigwigs fly in about 6-8 times per year, and I doubt they’re flying on their own dime unless they have a flight attendant in the family. So it feels understood that they won’t require anything they’re not willing to pay for or at least accommodate.

So far, so good!

3. I’m worried my coworker’s surgery will set the standard for how long I can be out for my wife’s (#4 at the link)

I asked if my coworker’s speedy recovery from the surgery would impact our boss’s perception of my similar leave request. Alison and commenters were unanimous: treat this with straightforward clear communication as you would any health event, whether or not it’s something that is common or that your organization has experience with. Thank you all for those responses. They helped me realize that what I was afraid of wasn’t getting the right amount of time off; it was fear of homophobia and transphobia.

What I didn’t disclose in my prior letter is that I am a cis woman, married to a transgender woman, and the surgery in question is gender-confirmation surgery. It’s weird and hard to say something like that to a supervisor at work compared to, say, “heart surgery.” Most of the time, more sensitive medical issues (because while all health information is sensitive, there is a spectrum and some things are more emotionally charged than others!) like gynecology issues can be glossed over with “I have a doctor appointment” but I was going to need to give some more detail and justification about this, because it requires a decent amount of leave. Your response, Alison and commenters, along with a column published shortly after about LGBTQ workplace issues, helped me realize that this request is no big deal.

I am openly lesbian in a red state. My wife is openly transgender in a red state. Yet 10% of her small company is transgender. They handled the transition of two employees with grace and inclusivity. Obviously my own work granted leave for my coworker to get gender affirming surgery. I’ve never had a coworker bat an eye at my having a wife. Our (deeply religious!) families have not only stood by us, but supported and loved us. Our insurance company has covered many transition related expenses. We have a thriving transgender community in our city. I know that some of this is luck, and some of this is privilege, but some of it is being fearlessly open about who I am. I always drop “my wife” in job interviews to see the reaction and find safe places to work. I rely on the LGBTQ chamber of commerce and word of mouth in the community to get a read on an employer. In a time when so many news stories feature backlash against the LGBTQ community I want people to know that there are safe spaces and success stories and that it isn’t all bad. I want people to know that you don’t need to live in fear.

Thank you to Alison and commenters whose responses helped me recognize what my real fears were. Once I recognized them, I put them to rest forever.

4. My coworker passes me messages “from the CEO” … that I think are really from her

I never felt comfortable with the potential trouble of alerting my CEO, so I’ve stayed quiet. Interestingly, I suffered a back injury that made me lay off my high heels, and the IMs seemed to stop around that time.

There’s still a weird mom-ish vibe to her texts (we are nearly the same age), but I mostly just try to ignore them.

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{ 37 comments }

{ 37 comments… read them below }

  1. Eldritch Office Worker*

    I read #1 too fast and read “am in a similar position with a different organization” like social situation I thought you got in the middle of another affair accidentally and I am SO GLAD THAT IS NOT WHAT HAPPENED

    1. quill*

      OP could be the Angela Lansbury of office affairs; instead of murder she wrote, it’s Adultery she wrote.

  2. Keeley Jones, The Independent Woman*

    #3 – I’m so glad you and your wife have such a strong community of support!! What a great update.

    2. MEH Squared*

      Agreed. This update made my heart smile, OP#3. I’m glad it worked out so well for you and your wife.

    3. Kimmy Schmidt*

      Someone must be cutting onions in here because boy are my eyes misty. I wish LW3 and her wife all the best.

    4. Robin Ellacott*

      Honestly I teared up a little reading this. I’m not in the US but I hear so much news that makes me gasp in horror that this is a good reminder that decent people will keep being decent even in a really nasty climate.

  4. CoveredinBees*

    OP3 I am so thrilled that you and your wife feel supported and safe. I hope the recovery is as easy and quick as possible.

    OP4 Sometimes things are just better off ignored for whatever reason. It sucks but not every workplace responds well to these things.

  5. RKMK*

    Wildly curious about how John’s friend feels about him being with his daughter, but thank god OP got out and Katie has support.

    (And did Tammy quit her “job” and did that old workplace actually get a functional assistant? I have all these gossipy questions.)

    2. Dust Bunny*

      I wondered if she was actually a friend’s daughter or if that was just a cover story for him hiring his very young, no-relevant-experience mistress.

      1. soontoberetired*

        I know we’ve had a few questionable hires at my company in the past (aka someone’s boyfriend or girlfriend) but at least here if you are having an affair with someone working for you, you might very well be terminated or demoted, or made to switch groups. We have clear guidelines you can’t manage someone you are related to, the dating is a gray area but not looked on with favor.

      2. Observer*

        I wondered if she was actually a friend’s daughter or if that was just a cover story for him hiring his very young, no-relevant-experience mistress.

        That was my first thought, too.

      3. kiki*

        I always wonder when people make up cover lies like that… they have to know that there’s a huge chance the lie will make things even weirder down the road, right? I once knew somebody who tried to cover up an affair by saying the person they were hanging out with was their niece. Okay, it’s normal to hang out with your niece, I guess, but really weird you were kissing her!!!!! John’s explanation is less weird than claiming Tammy’s a relative, but it still has the potential for weirdness, especially if anyone from work ever crosses paths with Tammy’s family.

        1. Dust Bunny*

          If they were thinking that clearly they wouldn’t hire their cheating partners in the first place.

        2. quill*

          It’s like they think that as long as they’re doing something suspicious, they may as well lie about it and make it worse!

    3. Where’s the Orchestra?*

      I think the most pressing question is was this a company that John owned – and if so how secure is the employment of anybody still working there?

      After all – contentious divorce, and I saw one of those divorces as a kid destroy an engineering firm. Thirty people abruptly unemployed because the owner had zero self control.

      1. Myrin*

        I think the most pressing question is was this a company that John owned

        From the original letter: “her husband (John) who owns a consulting firm in my field”.

        1. Where’s the Orchestra?*

          Thank you – didn’t go back to the original. Makes my concern about the financial stability of the company more pressing. Hoping other people don’t end up unemployed because John couldn’t keep it zipped.

  7. Observer*

    #1 – Boss having an affair.

    I’m SOOO glad you are out of there. Especially since, as someone else noted, there is a good chance that the whole company could be destroyed and you would then be out of a job.

  8. BlueMina*

    #3 sending you and your wife best wishes for the surgery! Your letter really struck a chord with me, I’m a transwoman in a deep red state, and I’m about 15 days out from my own confirmation surgery. I generally recover from surgery pretty well, so I’m anticipating about 3 weeks until I’m up and about fairly normally, but you’re right, it’s so hard to say how long the recovery will take. I’m so glad to hear that the two of you are well supported!

    2. tessa*

      I am in a deep red state, too, and want you to know you have all kinds of well wishes and support, even if it might not seem like it!

      Good luck on your surgery. ):

  9. Abogado Avocado*

    OP 3, I live in a red state, too, and you and your wife’s story gives me hope that change can come, even here. Thank you!

  10. KulklaRed*

    Letter #3 – you have me totally dissolved in tears. I am so very happy that you and your wife are doing so well. I wish you nothing but continued success and happiness. Your update is the most hopeful I’ve read in a long time.

  11. Meow*

    For #3 – is it really that unusual to be tight lipped about the specifics of a surgery? I feel like I’ve heard the exact phrase “It’s nothing life threatening, but I will likely need X days to recover” coached to me before. I’m asking this for my own benefit as well, as I am being evaluated for a surgery that I don’t really want to discuss the intimate details of with my boss either.

    1. Julia*

      I think this is the sort of thing that can vary by office culture. I’ve worked in places where no one would dream of asking for more detail about a health procedure and no one wants to know, and I’ve worked at places where it would seem odd to take a lot of time off for a procedure without letting people know more about what’s going on. I don’t think the latter kind of culture is really advisable, but I guess in some places coworkers are close and share a lot about their lives.

    2. kiki*

      I think it can be hard to for some people (myself included) to feel like they don’t need to justify the time off with details of the severity. So especially for surgeries that require more than a week off work or must happen at a time that’s inconvenient for the business, it can be hard not to feel as if you need to prove how necessary the time off is.

      In functional workplaces, bosses don’t require any sort of detail, they accept and trust that it’s necessary. Being tight-lipped is totally normal, you don’t need your boss to know any of the details about said surgery to approve any amount of time off.

    3. EmmaPoet*

      It depends on the office and the person. In my case, my manager is aware of my medical condition and has been really supportive when things flare up or I need a procedure. They know a little more detail than anyone else, and have been great about it, so if I tell them I need surgery, they’re right there making sure I can have the time. But if I had a boss who wasn’t so supportive, or who didn’t care for details, then I’d stick to that statement.

  12. Grumpy Elder Millennial*

    LW3, I’m so happy to hear that you have found the support and acceptance in your life and work that you and your wife (and all of us) deserve. Thanks for the uplifting update.

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