Asking out work colleague leaving soon

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I'm interested in a work colleague she was dating someone for 5 years and they broke up a few months ago.

I have trained her on some stuff and she is leaving soon so was wondering a good way to ask her out?

It's difficult with working from home and covid

Do you have a rapport with her? Is she someone who you would be able to start a casual conversation with?

Cause if you know she's leaving you could just tell her that you'll miss seeing her around work and ask if she wants to arrange to catch up sometime. That might get you a number to call and a vague intention to stay in touch.

If you do that she'll probably Intuit that you're interested and if she does seem keen to see you outside work then that's a tentative green light in my book.

If your only interaction with her is as a trainer then I'd say you're on shakier ground. I actually once did pretty much exactly this - asked a girl id barely spoken to but had held a candle for at work if she wanted to see me outside work when I found out she was leaving. It didn't go well and in hindsight I can see that it was creepy - I was a stranger to her. She was nice about it but I think I freaked her out a bit.

That's the danger when you have a small window of opportunity - there's no time to develop the relationship organically. But also if she says no then you don't have to see her every day - it's easier to move on.

Ask her out for lunch or something.

Or: is there a way you could, somehow, wind up in the same place for lunch? Perhaps you can say “mind if I sit with you?” Like you would for any work colleague. Maybe you’ll get lucky that way.

Or: if there’s a party for her leavetaking, you could ask if you could keep in contact. Or even if there isn’t a party, you could ask if you could keep in contact with her.

Come to think of it, the third option might be best.

I would typically have Lunch with her and the rest of the team that are in the office in the canteen or upstairs or head to the pub if it was a Friday lunchtime.

Ask her if you could keep in touch with her via Facebook if you know she’s leaving your company.

I didn't get a chance to see her before she leaves today. What would be a good way to ask her out in instagram dms?

Just ask her if she wouldn’t mind it if you kept in touch with her.