Be Prepared

Well, that’s gonna itch tomorrow.

Jon, an online find, treated our first date like a game of 20 questions, complete with well-thought-out, conversation-starting brain teasers that he’d clearly memorized many dates ago. What he hadn’t practiced, however, was how to seamlessly slip them into conversation. As soon as there was the slightest lull, he’d hit me with, What were you like as a kid? Or what’s the strangest thing in your refrigerator?

I tried to help him out, answering each question in turn and sending them right back at him. Unfortunately, his answers were as well-rehearsed as his questions, and they didn’t leave room for interruption. For example, I asked him his own question, How do you spend the first couple hours after work? He described a new exercise regimen he had developed for himself. When I asked him a follow-up question about his workouts, he looked confused; He hadn’t finished his spiel! “Well wait,” he said. “I also like to read.” Thank goodness he told me.

After two drinks, I was ready to call it a night, and I thought Jon was too, but his little play wasn’t over. After we got the check, he said, “I’d really like to walk with you to Bryant Park.” I hesitated, wanting to opt out, but he was a sweet kid and it was a beautiful night, so I said OK. After all, he seemed like he knew of something cool going on there, so it would probably be worth it. What I hadn’t really thought of was that we were a good 15 blocks from Bryant, and I was wearing my highest first-date heels.

On the way, he lectured me about the diet he’d developed to accompany his workouts, the “new Atkins,” he claimed. I tuned out after he said he’d eaten five slices of pizza for dinner that night. “Yeah,” I said. “I don’t think that diet would work for me.”

By the time we got to Bryant, my feet were torn up, but I put on a smile and suggested we sit at one of the public tables. Jon disagreed: “No, let’s sit in the grass!” So in the grass we sat. There was clearly nothing going on, and the park was actually clearing out. I’m a mosquito magnet regardless, but on this humid summer night, I could actually see the little bugs chomping on my legs. Still, in the grass we sat, as Jon went on and on about his pizza diet. That’s when the sprinklers came on.

He seemed utterly dejected as we walked back east. But at every street corner, he’d hopefully (and uncomfortably) place his hand on my lower back. I tried to make it clear that I wasn’t thrilled by physical contact, inching away and keeping my arms crossed. All I wanted to do was get out of these shoes and damp clothes and get some calamine on my burning bug bites. As we reached the point where we’d part ways, I turned to him to say “It was nice to meet you.” I only got out “It was nice…” before he planted an awkward peck on my lips. I guess I should’ve seen that coming. Picking up on social cues just wasn’t one of Jon’s after-work activities.

—Raz, 26, NYC