Dear Agatha,

Why is the gay world SO small? I ask because of something awkward that happened recently at work. I’m a 32-year-old guy, and I’m at a point where I’m finally feeling as though I’m actually in charge of my life. I have a job that I love and I’m good at. I attend weekly therapy to improve myself, and I have a strong support network of friends. Gone are the endless nights of partying and nameless hookups, followed by days of regret and shame. I felt like I finally had put all of that behind me…until a few weeks ago.

My boss at work announced he was moving out of state and would be working to find his replacement. After a short search, he said he’d found his replacement and introduced the company to the new guy the next day. My jaw hit the floor; it was a guy I used to fuck regularly when I was deep in my party days. His eyes met mine, and I knew he remembered me, too.

This guy, let’s call him Kevin, is my immediate supervisor. I answer directly to him for just about everything related to my position. I have several meetings with him weekly, some involving just the two of us. I also tend to stay late to accomplish extra tasks, as does he. We’re often alone in the office together well into the evening. Though neither of us has brought up our past, the tension is there, and my colleagues are beginning to notice. Even through the haze of my party days, nobody at work knew how wild I could get. I kept everyone oblivious. Now, my professional reputation could be at stake.

Should I force a conversation with Kevin about our past to clear the air and establish distinct, professional boundaries? Or should we continue not addressing it, as doing so could worsen the situation?

Thanks for any help you can offer!


Dear Brad,

This is a genuine case of the gay world being tiny!

You’ve already laid out the two options you have in this scenario. You can either pretend the tension isn’t there or confront it head-on. Let’s look at what could happen in either case.
It could stay hidden under the surface forever if you ignore it. It’s not impossible that Kevin could be a different person than he used to be, given all the work you’ve done on yourself to move your life in a direction you’re pleased with. But let’s be real: when has a problem like this ever gone away by ignoring it?

Addressing it with him in a matter-of-fact manner, acknowledging what happened once upon a time could be uncomfortable. However, it could also clear the air and give you peace of mind in the workplace. I don’t know how deep the connection went between you two. Maybe he was just a fuck buddy, or maybe there were deeper feelings there. Either way, an open and honest conversation might keep you from walking on eggshells around each other.

My recommendation is to talk to him about it. Allow yourself to own who you used to be and who you’ve become. It might make him respect you more and allow you to stand in your truth and be a stronger, better person.

Sending lots of love!