My question is not exactly high-stakes, but I’m having some anxiety about this situation all the same, and not sure what to do.
I (she/her) started using OkCupid recently, and a couple days ago, my coworker (he/him) who I don’t know well but see around often (we work at a very small company) sent me a message. I know it can be fun to send a couple silly messages back and forth when you see your friends on these sites without making it weird, but I don’t think this is that.
Anyway, if I see coworkers on dating sites, I think the polite thing to do is just ignore it and move along, so I was not super into the fact that this guy messaged me but I figured he was just being kind of socially obtuse. His message implied that he was going to ask me out “until he realized who I was,” which made me immediately uncomfortable. Dude, if you realized that, why did you message me anyway and tell me that?
I felt like ignoring him might make things weird at work, so I just messaged back noncommittally (like, “Ha, look who it is”), hoping I could move the conversation to peter out without making it awkward. However, things got awkward anyway, because coworker continued sending messages despite my polite attempts to disengage (“[Cool, unsolicited weekend plan you shared] sounds fun. Anyway, see you Monday!” …and then he’d send another message trying to continue the conversation.) I read and did not respond to the last message.
I’m sure I should communicate that I feel uncomfortable chatting with a coworker on a dating site, so do you have any scripts for that? Or would it be better to just block him and pretend it never happened? In hindsight, I feel like there are other things I could have said or done to end the conversation sooner, but that’s only now that I know I wasn’t able to end it without confrontation. It might be useful in general to know how to stop an inappropriate interaction like this in the future, so what would you have done?
It’s not inherently weird to be on the same dating site as other people you know in other contexts. It feels weird because the illusion of privacy has been punctured for a moment, but it’s not actually that strange. The awkwardness is in what people do about it.
I believe I have shared the story of the Shadowy Dating Juggernaut where Commander Logic and I and both of her roommates and a few other friends in the Bespectacled Bookish Brunettes of Chicago Knitting Circle And Culinary Society were on OkCupid at the same time, right? It was inevitable that streams would cross and one of us would bring a dude we were dating to a party and watch him slowly figure out where he knew the rest of us from…because if you liked one of us enough to write to you probably liked all of us…and that we all knew each other….and that we had definitely had been trading notes about him behind the scenes in the name of safety, solidarity, and hilarity.
When seeking romance (etc.) on the great wide Internet it is inevitable that we will run across people we know in other contexts. Like you, my strategy has been either to totally ignore it or to be like “Oh, ha, look who it is. See you at work, Work Person!” and then drop the conversation completely. Whether I ignored or said something depended a lot on context and the vulnerability of what was on display in their ad. “My mom and my friends say I’m funny and I like long walks on the beach and living life to the fullest” guy got a “hey, hilarious that we’re both here, good luck bro!” Someone revealing kinks or more explicit sexual content or desires just got ignored and in some cases insta-blocked more so that I wouldn’t make THEM uncomfortable or feel like they were being monitored. Mostly my attitude was “No shame, no foul, and no gossip unless you do something actually creepy.” And if it ever came up at work, I’d be like “Whoa, awkward, right? I won’t talk about it if you won’t, and heyyyyyyy good luck out there buddy!” #don’tcrossthestreams
Another true story: Years ago colleague who was new in town messaged me once on OK Cupid and we went for a friendly coffee before we knew we’d be working together. Then we got assigned to co-teach a class. Upon being “introduced” at work, we never mentioned or even hinted that we had met each other before in any other context. Yay professionalism!
If your coworker has got overall good intentions and is also feeling awkward about what to do next like, “aaaaahhhhh, I started this, do I have to keep emailing her now back and forth forever, ugh, so awkward?” he will gratefully take your lead. And if he’s not taking your lead, like now? Then don’t reply to anything else via the dating site, or, reply once to say “Hey, let’s wind this conversation down, I’m not interested in connecting here, see you at work” or “Hey, let’s block each other here so it’s not super-weird to have a coworker hanging out whenever we log in, ok? Good luck out there!” and then block him. Blocks are not mean. Blocks are often necessary to make a social site usable.
Then, keep work conversations only about work and wait for the awkward levels to normalize.
And, if your colleague won’t drop the subject and starts bringing it up at work, making you feel like he’s monitoring your dating and sex life, and making your life weird at work? DOCUMENT THE EVERLOVING SHIT OUT OF IT. America needs about 100,000,000 uncomfortable training sessions led by HR right now.