my boss from before my gender transition is now my colleague

This post was written by Alison Green and published on Ask a Manager .
A reader writes:
My first full-time office job was at an awful place. I was there for nearly three years before I was unceremoniously laid off, just a week before I was supposed to take on a new title and a raise. My boss, Marcy, handled it really poorly. It turned out that, although she seemed to be in my and my department’s corner, she was most certainly not. Our whole group was treated awfully with the acquisition that led to downsizing, and that’s not even getting into how overworked, underpaid, scapegoated, and frankly mistreated we were as workers.
Fast forward to fall 2020. On my second day of work, I realized Marcy works here, albeit in a totally separate department (in a company of about 300). I was startled but then realized it might not be an issue. At the time, I had two things working in my favor: I was working entirely remotely and I have fully transformed since Marcy last saw me. That is to say, she knew me as a twenty-something slightly-chubby young woman with a non-Anglo feminine name, and I am now a thirty-something fat dude with an Anglo name. I present as a man and use he/him pronouns at work, though outside of it, I’m out as non-binary and use they/them pronouns.
This year, we were mandated to go from remote to minimum twice-weekly in the office. There’s one day a week where everyone who doesn’t have a special exemption is supposed to be in, regardless of department. Wouldn’t you know it, the very first week they enforced it strictly was last week, and I ran into Marcy for the first time since she laid me off. Apparently we’re among the few who still mask and therefore eat lunch on the patio as a matter of course. I was writing when she came outside and while I registered her, I didn’t say anything. She was the one who engaged me in conversation for a bit. Before I left, she said she knew my name (new/current one, for the record) and introduced herself. I said, “Nice to meet you, Marcy” because I had no idea what else to do than roll with it.
This week, it happened again. She sat near me though there were other options and said hello to me. I was reading so I said hello back, but I didn’t disengage from my book. To be fair, I genuinely prefer a solo, quiet lunch as a break from all my meetings and other social interactions. Still, I felt rude because she seemed to want a conversation with me. It was really awkward.
I don’t know what to do, if anything. This has been so weird and I don’t know how to handle it. She could have known my name because lots of people at the office know me better than I know them; I do deliberately put myself out there whenever and wherever I can, both as part of my role and as part of the general office culture. But she also could have put two and two together. It’s not like there are absolutely no traits, habits, or features I share with my pre-transition self. Her (re)introducing herself might be a sign that she’s willing to start over with me.
If she hadn’t tried to engage with me so much, I wouldn’t care. Bluntly stated, I neither need nor want to be especially friendly with her. I simply don’t trust her. She was pretty sneaky and sinister as my boss. Her choices directly harmed me and had repercussions that affected me for years.
For now, I’m going to avoid being on the patio when it’s her lunchtime, but I can’t imagine this will be the only way I could have a run-in with her. Do I let her know that I know she knows? Drop hints and see if she takes the bait? Keep pretending like we’re brand-new colleagues? It’s weird and I feel weird.
I can see why you feel so weird and awkward — first, here’s the person from your past who was at the center of a really horrible experience at your old job and whose behavior affected you negatively for years. Second, there’s an information imbalance — you don’t know what she knows, so you’re left wondering and trying to figure out what she knows, and what that means for how you should respond … all without having any real information to use to navigate it. That’s incredibly nerve-wracking.
Here’s what I think: maybe she recognizes you and maybe she doesn’t, but so far she’s not indicating that she’s relating to you as anyone other than a new coworker she just met and so, at a minimum, there’s enough plausible deniability present that you can just go with that.
Best case scenario, there’s an opening for you to just model the relationship you want to have with her — which is as a new coworker who doesn’t work closely with her or know her well, and who doesn’t need to. You can be politely distant and see if she respects those cues.
If she recognizes you as someone she knew previously, there’s a decent chance that you demonstrating the terms on which you want to relate will result in those being the terms on which you do relate. And if she doesn’t realize you’ve worked together before … well, that’s still true. You will just be the politely distant new colleague.
The exception to this is if you would feel more comfortable raising it proactively. If you’d get more peace of mind from saying “I’m not sure if you realize we used to work together; I was on the X team at Y Org,” you can do that! (And I’d lean toward that if she starts treating you more strangely than she is now, as well.) Obviously that’s tied up with a bunch of issues around whether you’re out at work or want to be (which I am not addressing as a worry since you didn’t raise it) but if that would make you rest easier, it’s an option.
Thank you to Kalani Keahi Adolpho and Stephen G. Krueger of the Trans Advice Column for helping me think through my answer to this question.
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