Miss Information: Should I hit on my roommate if I’m not sure he’s gay?

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Hi guys, quick bit of housekeeping: I heard that some of you were sending your internet dating disaster stories for last week’s win a free book contest and getting bounce-backs to your email. The problem should be fixed now, so email me your story by end of day Sunday, May 16th. Keep it under 500 words. You can remain anonymous or have your blog, band, or questionably tasteful Etsy store hyped to your heart’s content. Rock on!

Dear Miss Information,

Should I make a move on my roommate? I’m not sure of his sexuality, but I do know that he’s smoking hot. We share an apartment off-campus and we’re both in our junior year of college at NYU. He brings girls over sometimes but none of his hook-ups last very long. I’m openly gay, which he says he’s cool with, as long as I don’t bring guys over. I told him that’s fine, as long he knows that the rule goes both ways and he can’t do that with girls.

He’s been respectful of that, though I have caught him a few times breaking the rule. Once I busted him and a girl coming out of our shared shower. "I was drunk" and "It’s college!" are his usual comebacks. He’s always walking the apartment around half-naked and making jokes like, "I’m so about to hump you, man," or "Let’s kiss!" but I can’t tell if it’s Andy Samberg-on-SNL-style-homoerotic/ironic fucking around or he really means it. If I came on to him and he rejected me, or worse, got mad, I’d feel really (really!) stupid. What would you do? — Bachelor’s Degree in Hesitation

Dear Bachelor’s Degree in Hesitation,

Let this one go.

Reason #1: He’s your roommate.

Best-case scenario, he reciprocates and the two of you start dating. It’s great for a few months. Then you start arguing over who left the milk out and who paid the cable bill. Romance? Gone. Sexual tension? Gone. Courtship is the fun part. When you skip ahead, everyone loses. Worst-case scenario, he gets offended, kicks you out or moves out himself, and then you have to find a new roomie.

Reason #2: He’s fucked up.

I’m talking about his sexuality, his self-identity, and — most of all — his emotional IQ. He’s comfortable living with a gay person as long as it’s on his terms, but then he goes ahead and breaks his own rules. According to his reasoning, getting drunk and disrespecting your roommate are an acceptable and a normal part of college, but it’s somehow deviant of you to want to have a guy over and smoke bongs and watch DVDs in the living room. He may or may not be a self-hating closet case, but he’s definitely a hypocrite. Why would you want to date him? He makes Andy Dick look like a dreamboat.

Reason #3: You’re in college.

Sure, he might be a good pick. If you were in prison or a tiny town in Arkansas and there wasn’t anybody better to choose from. You are a young guy, in college, in New York City, at a very cool (albeit expensive as fuck and I have no idea how you can afford it and I’m really very jealous) school. You could be meeting artists, filmmakers, financiers, and frat boys. This is the place that has it, whatever you’re into. Be like Pokémon collector and catch ’em all, except the ones with the big red flags who just so happen to live with you.

Dear Miss Information,

Around January 2008, I started seeing a girl and we fell in love. The sex was amazing, as was the connection and companionship. Fast forward to September 2009, and we split up. I was being too possessive and jealous. I had a (since resolved) issue with smoking too much pot, and she was needing space. When we broke up, something came out of her that was blocked. She told me she had a dark secret she’d never told anyone before, though I don’t know specifically what happened.

We had a turbulent time via texts and emails until we started getting back together around November of 2009. I had fixed my issues and things seemed okay. We went on holiday, spent lots of couple time together, and did lots of family things — weddings and so on — but during this time, she alternated between loving me and being emotionally unavailable.

Then I found out she had been having an affair with a guy she had just met. She messaged him in front of me to say I knew about him and that it was over between them. I also found out that she was seeing a different guy around the time we were getting back together. She broke up with him to be with me but relapsed at least once. I know she regretted it, but we ended up breaking up the next day.

We are in some contact and she is about to start therapy. She says she hopes to be able to talk to me about her issues. She says she knows that is what is wrong with her, but she doesn’t know how to deal with it yet.

If she is getting therapy and she can get past her depression, I feel that she might want to come back. I just don’t know what to feel about this, though. I do love her more than I ever have anyone. Can she truly fix herself, now she recognizes that there is something wrong and is no longer running from it? — In Love with Trouble

Dear In Love with Trouble,

You’ve got it all twisted, my friend. You wonder if she "might want to come back" when you should be questioning whether you’d even take her ass back. You feel sorry for her when you should be feeling sorry for you.

Everyone’s messed up, it’s just a question of to what degree and how it manifests itself. If smoking too much grass and being whiny when she goes out with attractive male friends are your only crimes, then it sounds like she’s got you way beat when it comes to having issues. This is assuming, of course, you’re not minimizing a raging drug addiction into "smoking too much pot" and a restraining order into "too possessive and jealous." You’re not holding out on me, In Love with Trouble, are you?

Issues are sad. We wish no one had them, least of all the people we adore. It goes against common sense to detach from someone when they’re having issues, but sometimes it’s the only decent thing we can do.

Otherwise, you’re teaching her that dealing with her deep dark secrets by cheating on someone is acceptable and that you’re cool with being a source of feel-good comfort and judgment-free reassurance as she continues to run from whatever’s plaguing her. If there’s even something plaguing her. I’ve known a couple people who’ve invented or trumped-up stories in order to dodge responsibility for their mistakes. Not saying that’s your girlfriend. Just saying you should be wary.

Can she overcome all her bullshit and be a good girlfriend to you? Sure. But you must separate from one another for a while and let her figure out her shit and you figure out your shit and let everything rest. Don’t be friends. Be friendly strangers on sabbatical.

Go to therapy yourself if you think you need it, and try to meet some other girls. There are relationships that are easier and much more enjoyable than this one, I guarantee you. Once you’ve been outside your microcosm of drama and bullshit, I doubt you’ll want to return. If you do, then you’ll know it’s meant to be, whether you get back together as happy, healed adults or co-dependents who grow up to raise little mini-co-dependents in their own image.

Readers, have you ever bought the "I’m a fucked up person" defense when someone’s cheated on you? If so, what were the circumstances?