Over the holiday break, a long-anticipated milestone finally happened: Bobby met Amy’s boyfriend for the very first time.
They’d been dating for about a year, which made the delay feel, noticeable. Not dramatic, not scandalous, just one of those things that kept almost happening but never quite landed. And because it wasn’t happening organically, it started to feel like a thing. No one wanted it to feel like a double job interview. But no one wanted it to keep being avoided either. So, naturally, the solution was Christmas presents.
What was supposed to be a simple gift exchange quietly turned into “Okay, now’s the time, bring him” according to Bobby. But Amy said the final push came from Bobby's wife, Caitlin, who essentially said, “Enough is enough. This is getting ridiculous.” And just like that, the meet-and-greet was on. Amy and her boyfriend came by the house, gifts in hand, shoes still on (an important detail, apparently), and everyone immediately sat down on the couches no one ever uses — the “company couches.” The kind of furniture that only exists for moments exactly like this.
And then… they talked. Well, some people talked. Amy and Caitlin carried most of the conversation, chatting comfortably back and forth, while Bobby and the boyfriend mostly listened, occasionally chiming in. There was no dramatic first impression. No big bonding moment. No awkward confrontation either. Just four adults sitting in a living room, making polite conversation, breathing the same limited supply of oxygen.
Bobby later admitted it felt strange, sitting on unfamiliar couches, talking about life, without any easy escape like a dinner reservation or activity. No tour of the house. No “Hey, want to see my basketball court?” No pickleball invite. Just… sitting. Still, there were small moments. The boyfriend talked briefly about having kids and the experience of bringing a newborn home from the hospital. Bobby listened. Everyone nodded. Time passed faster than expected. And then it was over.
The official verdict? “He seemed nice.” No red flags. No weird vibes. No strong opinions either. Just… delightful. Later, Caitlin followed up with Amy to say that while no one was seeking approval, the boyfriend got an A+. Bobby clarified that the grade was mostly Caitlin, his own assessment was more of an “A-plus TBD.”mAll things considered, that might be the best possible outcome. No forced bonding. No awkward dinner. No overthinking. Just breaking the seal. Because sometimes, meeting your coworker’s significant other after a year doesn’t need fireworks, it just needs to happen.