Bonnie Siegler | Dear Bonnie

Lovelorn in Louisville

Dear Bonnie,

Help! I think I'm in love with my coworker! She’s a single girl, I’m a single guy, we flirt all the time. It’d be perfect if we didn’t work together. Do you think it’s a terrible idea to ask her out for a drink? Our studio is pretty small (ten people) so lots of potential for awkwardness if it didn’t work out.

What should I do? Is it possible to have a successful office romance in such a small working environment?

Lovelorn in Louisville 

Dear L.,

If you really, really think there is a possibility that this could be a genuine relationship, you should definitely ask her out. Think about Charles and Ray Eames! Saul and Elaine Bass! Massimo and Lela Vignelli! How could you pass up this wonderful opportunity?

That said, you have to proceed with caution. Hope for the best and prepare for the worst. The best is that you guys get married and you name your first child Dear, after me.

The worst is that one of you ends up heartbroken. Could you work with her after the break up? Take a minute and imagine spending every day in the same room as each of your exes. Now, I ask again, could you work with her after the break up?

Another thing to keep in mind is the pesky hierarchy that exists at most offices. Your future could hold a resentful junior colleague ignoring your critiques or a more senior person you used to date telling you what they don’t like about your work. This possibility shouldn’t necessarily stop you, but it's worth considering. Also, I don’t think the size of the office plays a role here. A really big office with an ex in it can feel very, very small.

Ultimately, life is more important than work. (There, I said it.) So I say go for it. And even if she says no, taking a risk can be its own reward.

P.S. Two designers who met in my office years ago eventually got married and are living happily ever after. (Hi Allison and Mark!)

We want to hear from you! Send your questions for Bonnie to [email protected]

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