Hey Meredith,

I’m a man in my mid-30s. I’ve never dated a lot, although more in recent years, yet I’m still a total introvert. And socially awkward, but that’s for another time. A couple months ago, I had my first true one-night stand. A 30-something woman from out of town matched with me on Tinder and before you know it, we’re out getting drinks and having a blast. I left her hotel eight hours later and fun was had by all. We said we’d look each other up if we were ever in the other’s city, but you know how that goes. At the time, I sensed a connection (and I don’t with most people), but I didn’t want to be “that guy” who clings. I sent her a short text the next day thanking her for the nice evening, and that was it. I’d think about her on occasion; every once in a while when our favorite teams were playing each other I’d consider sending her a teasing text, but never did.

Then a few weeks ago, a female friend and I decided to make a trip up north to this woman’s city (she’d never been there). After some hemming and hawing, I dig up the girl’s number and sent a text with no expectations of a reply. She wrote back and said that she’d love to get together for a beer, but that she now had a boyfriend. I was fine with that. Me and my friend spend the day in the city, then meet up with the girl at the end of the day. We went out and grabbed a beer and just chatted for an hour or two. I sensed that connection again. My friend also said that she sensed something between us. We went our separate ways at the end of the night and then did the stereotypical 2016 add-me-on-Facebook deal. I’m confused. I can’t tell if I’m just romanticizing the whole idea of this or whether there’s something legit. And no, I don’t want to be a home-wrecker. I just don’t know how much I can push the envelope contact-wise, or whether I should even spend my time doing so. Any thoughts or answers? Thanks.

– Stupid Is, Stupid Does