“Jaw With John” – Don’t Overthink After-Work Drinks

I recently ran into an old friend (and former colleague), and we set up a date to have after-work drinks in a few weeks to catch up.

Three years ago I asked her out on a date, but she declined because she was in a relationship.

Last year we were scheduled to do drinks (as friends) and her boyfriend vetoed it at the last minute, saying he felt uncomfortable.

I had forgotten that. How should I ask if he’s now comfortable with it, if he’s even still in the picture? — Ethically Conflicted

Dear Conflicted:

You’re an adult. She’s an adult. You don’t need to ask if she is still with that boyfriend. She is capable of making her own decisions and that should tell you that it’s OK for the two of you to meet up.

The purpose of said after-work drinks is to find out what each of you has been up to since you last saw each other. Don’t overthink it. Said boyfriend might be out of the picture. You won’t know until you see and talk to her. And if he isn’t, then this rendezvous might be canceled again.

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