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Boston.Com Love Letters - I May Be Dating Somebody My Buddy Used To Bang



From Boston.com Love Letters


The Question

A few months ago, I began casually hanging out with a former co-worker. Things progressed and we began hooking up once in a while. At first I thought we were “just having fun,” but things have progressed. The problem is, years back, I was informed by another co-worker that the girl I’m now seeing used to hook up with another former co-worker, who happens to be a close friend of mine. Should I confront the woman that I’m now seeing and ask if she did sleep with a friend of mine? Or should I just chalk it up to everyone has a past and this happened before we began dating? I can’t lie – this has been in the back of my mind and I am not sure if I need to say something or if I’m better not knowing.

– Confused At Work

Hoss Goldstein’s Answer

You’re better off not knowing – or caring. It’s none of your business, and you wouldn’t gain anything by asking for details. You don’t seem to be worried about how your close friend will handle your new relationship. It sounds like you’re just curious, which isn’t a good reason to start prying into this woman’s past.
Also know that if she had been an important part of your friend’s life, you would have heard about it. Your close friend hasn’t brought it up, which means the hookup wasn’t a big deal – or it didn’t happen.

Readers? Didn’t this sort of happen in “Office Space”? Should he ask about the rumor?

– Meredith


El Pres Answer

Per usual Hoss Goldstein is living in a little bubble called fantasy land. Because here is fact. You can’t date a chick that your buddy used to fuck. It’s even worse if they weren’t really dating or serious. He just called her up late night when he was bored and did all things you can do to a girl you don’t date. I’m talking vile shit. Now you’re holding hands having missionary sex like she’s some choir girl. But I the back of your mind you know when she gets bored she’ll run back to your buddy so she can let her hair down and get fucked like a dirty whore. Nope can’t have it. Listen I’m not saying it’s right. I’m not saying it’s fair. But knowing your buddy fucked your girlfriends brains out will mess with your brain. It’s not worth the headache. Just find somebody new and call it a day. That’s the best advice I’ll give all year.