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. 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 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.” Amy and her boyfriend came by the house, gifts in hand, shoes still on and everyone immediately sat down on the couches no one ever uses, the “company couches.”
And then… they talked. Well, some people talked. Amy and Caitlin carried most of the conversation, chatting back and forth, while Bobby and the boyfriend mostly listened, occasionally chiming in. 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. Still, there were small moments. The boyfriend talked briefly about having kids and the experience of bringing a newborn home from the hospital. And then it was over.
The official verdict? “He seemed nice.” 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.” All things considered, that might be the best possible outcome.