Life Advice



Ask Amy: Online dater is matched with a real-life crush

Amy Dickinson, Tribune Content Agency on

Dear Amy: What is the proper way to handle being matched on a dating site with someone you’ve previously met in person?

I am 51, professionally successful, and single.

I recently matched online with a man I met through a networking opportunity a few years ago.

He helped to coordinate my interviews at the company he worked for.

Just before the pandemic, he suggested finally meeting in person, as my interviews had gone well, and even if they didn’t hire me for that position, he wanted to stay in touch.

We met for coffee and had a good conversation.


From a networking perspective, it was a success. He was also one of the nicest and most attractive men I’ve ever met – honestly, it was hard to focus.

I’ve had no contact with him since, over two years ago, and I just “matched” online with him!

If he asked, I would go out with him in a heartbeat.

But if he’s not interested, I don’t want to ruin a professional contact.


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