I missed an opportunity

Send your own question about friendships, dates, no dates, love, divorce, breakups, and families through the anonymous form – or email [email protected].

Q.

I’m dealing with a situation that feels like a missed opportunity, and I can’t stop thinking about it. On a recent work outing, I ran into a familiar face, but I couldn’t place her at first. She stood out to me, like someone I’d known in the past, but I just couldn’t figure it out — until I noticed her name tag.

That’s when it hit me: high school.

I should have just talked to her, but I hesitated because I couldn’t remember how much, if at all, we actually interacted back then. It wasn’t until after I left the event that I realized I’d made a mistake. I should have said something.

Now what?

– Missing Out

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A.

This is what Google is for.

From there you move on to Instagram, Facebook, or even LinkedIn.

Sometimes social media is just 1,000 AI-manipulated photos, weird selfies, or shots of decorative pumpkins.

Other times these platforms can help you find a person you’ve been looking for – maybe someone who wants to be found.

Locate her online and see if you can figure out if she’s coupled. If she seems available, tell her you regret not saying hello. Explain that it took you a beat to figure out how you knew her.

Then say a few nice things and ask one or two questions. This isn’t complicated, and it doesn’t have to be weird.

If she ignores your note or responds without enthusiasm, take the hint.

But try. It’s not too late.

– Meredith

Readers? Would it be weird to reach out now? What would you say?

Send your own question about friendships, dates, no dates, love, divorce, breakups, and families through the anonymous form – or email [email protected].

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