Love Letters: I Don’t Want To Be Creepy

Dear Meredith,

I'm going to be moving from my current job to a new opportunity in the next couple of weeks. I work with a small group of people, one of whom I am quite attracted to. Since we work together, I have not acted on my attraction, and I have probably been more aloof with this person than with others in my group. Now that I will be moving on, I want to show my potential interest to this person.

My question is, how can I do this without being creepy? To complicate matters, I was in a very serious relationship when I started this job, but that has quietly ended. I'm pretty sure there is no reason for this person to even know I am now single. Under normal circumstances I would think a subtle “let's meet up for drinks sometime” would suffice, but in my case “let's meet up for drinks sometime, and by the way I'm single now and I think you're pretty hot” is a bit less subtle.

And if I go through with it, what if he tells the whole office after I'm gone? I might work with some of these folks again in the future. Is it always creepy/unprofessional to ask out someone you work/have worked with?
Thanks for any advice!

– Trying not to be Creepy in Cambridge

It's not creepy to ask him out for a drink. "Let's meet up for drinks sometime" is a fine, simple request. You can get into the "I'm single and you're hot” stuff once you're actually out for the night.

If you're concerned that the drink request will confuse him -- because you've been aloof and he doesn't know that you're single -- ask the entire group to hang out after work to celebrate your departure, and then, when you're all relaxed, get to know him better. See how you guys get along outside the office. If it goes well, you'll feel less creepy about asking him out on a real date.

Readers? Should the letter writer go out in a group first? What if her co-workers talk about this after she's gone?

– Meredith