Do I Ask Out My Work Crush?

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So I’ve been really into this guy I work with (we are both employed by different companies but our paths cross as we work on the same large-scale project). I am totally professional and he has no idea that I have been crushing on him for almost three years. I have memorized all of the relevant lines from the movie “He’s Just Not That Into You” – how if a guy wanted to date you, he will make it happen.

“My guy” has never made a move. So I don’t have any grand ideas that he is crushing me back. I also know is he is single. Before COVID, I would see him about once a week, but since the pandemic began, we are 100 percent remote, so all communication is via company Skype/email or conference calls.

I have recently accepted another position in a different company/different venue where I will no longer work with him. As I prepare to leave, do I say something to him? Do I send him a Skype letting him know it has been a pleasure working with him and hope our paths cross again? Is that too polite and not direct enough? Or do I hope he says goodbye and takes the initiative to ask for my personal contact info?

– Leaving


Do not take the screenplay of “He’s Just Not That Into You” as a guide for dating or life. That movie has a lot going on, and some of the people who are into each other in the film don’t even wind up together. Also, it’s a 2009 movie based on a self-help book published in 2004.

In real life, 2022, everything is different. People have changed a lot over the past few years. You have no idea what this man thinks about, who he’s with, what he’d be open to, etc. You’ve respected all workplace boundaries, but now you’re leaving. It’s a great time for you to ask for what you want.

How about, “Hey, I just wanted to let you know I’ve taken another job. It’s been so great to work with you, and if you’re up for a drink, walk, or some kind of appetizer, I would love that, but no pressure.” Something like that.

It’s a gesture. It’s nice. It hints at interest without any declarations of love. It’s shooting a shot, and it gives him plenty of space to back away slowly, if that’s what he wants to do.

If it feels like too much, you can ask a few people for an evening out and then see how it feels to be with him in a group, outside of work.

Then maybe the movie rules can apply. If he rejects or ignores the request, send your contact info and move on.

But you’re not there yet.

– Meredith

Readers? How would you ask?

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