Should I Contact a Guy from My Past?

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Hey Wendy,

I have confusion about a guy I was interested a while back — I still have curiosity and lingering interest.

A year ago, my yoga instructor and I became friendly while I was his student, which lasted about six months. Right around that time, his partner left him without warning…He was hurting a lot.

I did get his phone number back then, but never called him. He didn’t seem that interested at the time. Now I hear he’s moved out of town, a couple of hours away.

What’s the protocol, if any?

Wondering about sending a text to connect with him?

Kat N.


Hey Kat,

I think it’s pretty sweet that you had the opportunity to be a new, friendly person to your yoga instructor at a time he really needed a kind (and possibly flirty) connection after the rug-pull end of his relationship.

To receive a text from a friendly past student saying, “Hey! I was just thinking about you! I hope your life is going well…” would likely be a positive experience for him. Most of us appreciate being thought of and welcome well wishes.

So, sending a “hope you’re doing great” text to someone you once knew gets the thumbs up from me.

Now let’s talk about what’s really going on here: You’re feeling—and I’ll just come out with it—desperate. Do you know how I know this? Your thought process is very recognizable. As in been there, done that. You’re feeling like there’s a shortage of good, available humans out there for you to connect with. When you’re dealing with a dearth of new qualified candidates in front of you, what seems like the next logical step is to look back through your past and see what you might have missed. Anyone who had potential is worth circling back for, yes?


Two hours away from your life? Nah-ah. Even if he was interested in reconnecting (which is a long shot), that’s long distance, and I don’t encourage long distance.

This is not the best use of your time, energy, and focus if you’re trying to find love. And your time, energy, and focus are precious resources, so spend them well, or risk burnout.

Instead, focus on meeting shiny new people who are open to you now. Date the ones who are available for a relationship, and are excited to see you, and can be on your front doorstep in less than an hour.

Where do you meet these new, shiny, available people? Online. Sorry, but that’s what we do now. It’s where the guys are (unless you count the guy who drops off your Amazon packages). I mean, what are your other options? Chatting up the guy who trims your neighbor’s grass? Taking a seat next to the retiree reading the paper in Peet’s? I’m not trying to be a downer here, but for some of us, our everyday world can get very small.

One more hot tip for avoiding desperation delusions: When you’re in the “there’s no one here” zone, you may also start to have fantasies about your exes. Maybe you’re still getting over the last one, but the one before that? I wonder what he’s doing…It’s another natural thought pattern. Your creative mind may paint him as way more amazing than he really was. But you don’t need magical thinking right now, you need practical magic—with a focus on the practical.

Keep moving forward, sweet girl. The new one for you is from your future, not from your past.