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

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.

My choices are: I can do nothing.

I can block him so he can’t see my profile.

Or I could send him a “smile” or message through the app or email, acknowledging the match and indicating interest in a date, while magically and simultaneously protecting future professional contact and not embarrassing myself.

I think I’d rather take a chance on love than a new job, but I feel so awkward and so far out of my comfort zone.

Maybe he has the exact same dilemma as I have regarding professional vs. personal contact.

What do you think?

– Woman On the Fence

Dear On the Fence: This is a great question, and as this plays out we either have the first scene for a galloping workplace rom-com, a fantastic story to tell at your wedding, or a neutral but nice near-miss. I don’t really see a huge downside for you.

In my opinion, the fact that – pre-pandemic – this man chose to meet you in-person after coordinating interviews (which did not lead to employment), indicates some interest on his part.

Now that Cupid’s algorithm has matched you, you could respond with a short note: “Hi. I remember meeting you for coffee back in the ‘before times,’ and thank you again for meeting me that day. I eventually got a job at Cybertech and have been mainly working remotely lately. Your interviewing coaching did help! Are you still at TechBubble? I suppose it was bound to happen to someone at some point but honestly, I have never been matched online with someone I’d met IRL. Awkward, for sure – but funny, too.”

That’s it. Leave a response to him.

Dear Amy: I am an old grandma with 10 step-grandchildren, the youngest of which is 18 and in her first year of college.

That child receives a substantial scholarship from me for her college.

Of the 10 grandkids, she is the only one who does not follow me on my cat’s Instagram account, which has over 5,000 followers.

She does follow her other grandma on Instagram, which is perplexing to me.

Not that I am begging for followers, but I think it's a charitable and loving thing to do, especially when I have been generous and loving toward her.

I have not discussed this with her mother.

Am I wrong to think that would be a loving thing for her to do?

It's just a cat account for Pete's sake!

– Upset Grandmother

Dear Grandmother: Yes, it’s just a cat account, for Pete’s sake.

And yet, for you it doesn’t seem to be just a cat account.

You have been careful to mention your financial support to this granddaughter. Are you implying that you are buying followers? I hope not.

Ask your granddaughter: “Did you know that ‘Muffin’ has become an Instagram influencer? I’d love it if you would follow the account. I’m having a lot of fun with it.”

It is not fair for you to imply that this is a primary way for your granddaughter to love you.

It is one way for her to love you, but it is not the only way.

Dear Amy: I liked your response to “Estranged,” but it didn’t go far enough. Estranged and her brother were dealing with a mother who had taken extraordinary steps to contact them.

I was surprised that you didn’t mention the possibility of them getting a restraining order. Their mother is stalking them.

– Been There

Dear Been There: Several readers mentioned this. Thank you all.

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(You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)