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When there's a four-year gap between your first and second date

Hey, girl. I should have followed up.

That’s the Ryan Gosling synopsis of an email exchange I had recently.

If you’ve ever been single, this has likely happened to you: You go on a good – maybe even great! – first date. And then you never see the other person again. It’s as if a budding connection is lost to a Bermuda Triangle bar owned by OkCupid. You wonder what might have been and eventually move on.

In 2011, I had one of those good first dates with a person who vanished. And I had forgotten all about it, until Mr. 2011 emailed in June to congratulate me on the launch of my Washington Post blog Solo-ish – a mutual friend had posted about it on Facebook, and it popped up in his news feed.

He had thought about our date, he wrote, and how we never had a second: “It was a great date, by all accounts,” he wrote. “And then we never saw each other again.” Sometimes your face pops up on “suggested people” emails from LinkedIn, he wrote, “or I’m just generally thinking of dates past – and yours jumps out to me, and I wonder.”

Oh, and by the way: He now lives in Portland, Oregon.

While I hadn’t been dwelling on this date the past four years, once I read his email, the details of that night came back to me. We’d gone to Bar Pilar on 14th Street, back when the neighborhood was much less of a scene. He seemed cute and nice; the conversation flowed. We had friends and professional stuff in common – we’d even gone to the same summer camp while growing up in Northern California.

I remember being bummed that he didn’t follow up – and of course, I could’ve asked for a second date and didn’t. Instead I wondered in the days after that date: Did I gossip about my work colleagues too much? Did he care that I was a year older than him?

Silly preoccupations, but I was a less confident dater back then. In my 20s, I often assumed that a good connection that went nowhere was somehow “my fault.” I took rejection more personally than I should. This was one of those times.

So it was refreshing to hear him explain that 2011 had been “early days for online dating” for him, “and I remember feeling inundated by how easy it was to meet women.” He went on: “My guess is that I had many first dates around then, and didn’t fully appreciate how rare it was to have one go as well as ours seemed to. Yours is the only one in that timeframe I even vaguely remember, and I regret at least not following up.”

See. It wasn’t about you, Lisa, and you being a gabby older woman (or at least not entirely!). It was a good reminder that, as much as self-reflection is important, you never really know what’s going on for the other person, especially when you barely know each other.

We chatted by email a bit more: about our 4-year-old date, about the woes of online dating in general and about how Portland’s singles scene differs from Washington’s.

When friends said things like “You’ll be planning a trip to Portland soon!,” I emphatically said no. It was satisfying to have this mini-mystery from my dating history now solved, but that was enough. Besides, another lesson I learned in my 20s is that relationships that live mostly in your inbox are tedious and rarely go anywhere.

While I wasn’t in the market for a pen pal, we kept writing. A few weeks in, he mentioned that he would be to Washington soon. “I thought it would be fun to meet up if you’re around,” he wrote.

“How about Bar Pilar?” I responded the next day. “I feel like returning to the scene of our first meetup feels appropriate, no?”

Bar Pilar has improved with age: There’s an upstairs area that wasn’t there in 2011, when we had to hunt for two stools next to each other. And my date had, too: He was cuter than I had remembered, and we were freed of that first-date pressure. Rather than two strangers from the Internet sizing each other up, we were two almost-friends catching up because we were curious about each other.

But that’s all it was.

As we chatted about our lives, our respective cities and the relationships we’d had since we last saw each other, I realized: We made the right decision the first time around. We might have been a good match on paper, but there wasn’t much chemistry or sizzle, as I like to call that ever-elusive “spark.”

“Just so you know,” I said as we wrapped things up, “I don’t think we missed out on anything here.”

He looked a bit startled, and I felt bad for being so blunt.

But I wanted him to know: By doing nothing after that good first date, we’d both done the right thing.



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