How to Spin Social Media Flirting into an IRL Connection

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Hey Wendy,

I just reconnected with someone I knew 20 years ago. We’ve been Facebook messaging, sometimes multiple times a day. We complement each other on things we post, ask questions, and so on.

How do I move this from Facebook to phone to IRL? Any suggestions? BTW, he’s a musician like your partner, which is how I saw him again, but I don’t want to just show up at his gigs. What should I do?

Ann T.


Hey Ann,

This one’s easy:

“I’m happy we’ve reconnected again. Hey, I see you’ve got a gig next Friday. I might stop in!”


“I’m thinking about coming to your gig next Friday. Would you want to grab a (drink/coffee/meal) with me before then and keep catching up?”


“I miss live music so much, and I’m looking forward to getting out again. When’s your next gig?”

He may be a bit worried about making the first move—especially since you have history. As a guy, he likely feels saddled with the responsibility for making the first move, and also wants to be considerate of you. He’s also probably thinking things like “Does she like me or does she like-like me? Is her interest in me simply the kindness of an old friend? Is she just being polite?” You get the idea. Add to that the pressure-cooker of the pandemic and the myriad differing opinions on stepping out IRL safely and what you’ve got is a recipe for hesitancy and second-guessing.

It’s a lot.

You could be the one who makes it easy for him to reconnect with you IRL—just use some variation of one of the lines above and see where it takes you two.

One last thing: I’d skip the phone altogether. We’ve all been way too cooped up and too disconnected from others for too damned long, so mask up, bring that pocket hand sanitizer, and go have some facetime (not just FaceTime).

Good luck!