Miss Information

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I am starting to fall for my roommate's ex. Is it ever going to be okay to date them?

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Dear Miss Information,

I recently moved to a new city. I don’t know a lot of people here other than my old friend Dan, who I grew up with.  While I was couch-surfing and apartment hunting, Dan recommended his girlfriend (let’s call her Cassie) as a roommate for me, since she was about to sign the lease on a great new apartment and the girl she was supposed to live with flaked out at the last minute. The apartment was gorgeous and Cassie seemed nice, so I went for it. Just after Cassie and I signed the lease together, she and Dan broke up.  Cassie and I have lived together for a few months now and get along well, and I still hang out with Dan pretty regularly despite living with his ex. The only problem is, I’ve been developing feelings for Dan that are more than friendly. I’d really like to pursue something with him, but don’t want to ruin a good living situation with his ex. Help!

—Messy Roommate


Dear Messy Roommate,

Oof. I don’t envy you – this is messy indeed. You’ve got the double whammy here of how to strike up a romance with a friend, and how to keep that friend’s ex feeling friendly toward you, plus the added stress of not wanting to jeopardize the elusive great apartment. So let’s start at the beginning: before you drink four glasses of wine, try to make out with your childhood friend, declare your undying love, and seriously piss off the person who knows where you sleep, slow your roll. A word of warning before you potentially complicate two important relationships: be sure you really like Dan, and not just a friendly, familiar, ruggedly handsome face in a new town.

Next, do you get the sense Dan feels the same away about you as you do him? Does he act like a platonic friend, or is he especially flirtatious with you? Do you guys end up spending tons of  borderline date-y time together, texting and calling each other even when you don’t have plans, or is it an activity-driven, let’s-catch-up kind of friendship?  Do you get that “I’m into you” vibe from him and feel that sense of “will-we-or-won’t-we?” tension?  Think on that before you make your move. And bear in mind he’s just gone through a breakup – there’s no guarantee he’s looking for anything serious right now, in which case you’ll have to move on. 

Speaking of the breakup, what were the terms of that? Who dumped who? Was anybody heartbroken here? Was there cheating or major drama? Or did the relationship just kind of run its course? This should all figure in to how lightly you tread with both Dan and Cassie.

But assuming your feelings are real, and mutually felt by Dan, you’ll have to eventually tell Cassie. You don’t have to tell her until things start moving in a serious direction. If your spark with Dan dies out instead of bursting into hot, hot flames, there’s no reason she’d really need to know. But if this relationship does get off the ground, put yourself in Cassie’s shoes: can you imagine a social situation more horrifying than getting up in the middle of the night to get a glass of water and seeing your ex getting busy with your roommate on the couch? (Okay, yes, the rabbit hole of horrifying social situations goes unbearably deeper than this, as readers of this column no doubt know, but still! No fun!)

If you get to the point where it’s time to talk to Cassie (aka: Dan is going to be your boyfriend and you’ve been keeping things under your hat and out of your apartment until they’re serious enough that Cassie really needs to know), break it gently – not when she’s just gotten home from work and she’s just trying to make some mac & cheese and forget about her day, goddamnit. Maybe plan it out, greet her with a clean apartment, a bottle of wine, and her favorite takeout. When you talk to her, you want to be clear, and direct but gentle. 

Tell her you know it’s an odd situation, but you and Dan are seeing each other. You’ll want her to know that anything between you and Dan started after they broke up. Be sensitive to her feelings and let her know that you feel just as weird (okay, almost as weird) about the situation as she does, and that you want to be as respectful as possible. 

Hopefully she’s understanding about everything, and will appreciate your honesty and forthrightness, though you can maybe expect things to be weird between you two for a little while. But if she can’t take it like an adult – and she should; there’s no code saying a roommate’s exes are off limits—there’s always the option of moving out and letting her sublet your room to someone else (for her sake, I hope it’s someone with a radically different type). After all, if you have to choose, true love is harder to find than a good apartment. Or not. Good luck!

Image via Flickr.