My coworker challenged me to a game of pool after work. "If I sink this, you owe me a kiss," she said, chalk in hand, this dead serious look on her face like she just proposed the most normal wager in the world. And I remember standing there thinking, there is absolutely no version of this evening where I come out unaffected. My name's Ben. I'm 27.
I live in Chicago. And my co-orker, the woman at the center of this whole story, is named Hannah. We both work at a midsized advertising agency downtown. her and account management, me and creative, different departments that intersect just enough to put us in the same meetings a couple of times a week without actually working directly together most days. I'd known Hannah for about 2 years by the time this story happened. In that specific way, you know, co-workers at a company big enough that you're not on the same team, but small enough that everyone still generally knows everyone.
I want to establish upfront that Hannah and I had a genuinely fun rapport for most of those two years. The kind of co-worker relationship built on shared eye rolls during long meetings, inside jokes about our mutual boss's inability to ever end a call on time, the occasional lunch when our schedules happen to align, but it stayed firmly in that lane. Co-worker friendly, nothing more for the better part of 2 years. I noticed she was attractive. Obviously, I'm not going to pretend I was oblivious to that.
But there's a specific kind of restraint that comes with working alongside someone. This instinct that says, "Don't mess this up." Because unlike a bad date with someone from an app, if things go sideways with a co-worker, you don't get to just move on. You still have to see them in the breakroom every day. Still have to sit across from them in meetings for the foreseeable future.
The night this whole thing changed started on an ordinary Thursday in October. Our whole team wrapping up a genuinely brutal week. A client presentation that had gone through about six rounds of revisions before finally landing. Everyone running on fumes and cheap office coffee by the time Friday finally showed up on the calendar. Someone in our department, a guy named Derek from the media planning team, suggested we all head to a bar down the street to decompress.