Ask Anna is a sex column. Because of the nature of the topic, some columns contain language some readers may find graphic.
Dear Anna,
I have been hooking up with my roommate for the last seven months. She came out of a bad two-year relationship, where she was cheated on. At first I was just a friend who wanted to help. I tried to steer clear of dating her at all costs to avoid any torment of being with someone who was just down the hall. Now things seem to be unraveling. Communication has ceased to just minimal talk about things like laundry. She no longer pays rent. Not sure what I did wrong. We went on a few trips that I’ve paid for. We started getting into fights on these trips. I always feel like a bad guy here. We are not official. Things are still strictly “just friends who hook up once in a while.” But I feel like I’m getting all the bad things that come with a relationship and I’m not in one. Not sure what to do at this point. Ask her to pay rent? Ask her to move out? Keep trying to understand her? I’m so confused. Please help me.—Roommate Dating
Dear RD,
She sounds like a less-than-stellar hookup and a downright appalling roommate. And you’re kind of her sugar daddy, but you don’t want to date her? This kind of confusing situation is exactly why we tell people to not schtupp their roommates. Let this be a teachable moment: Screwing where you poo is not as fun as it appears to be on “New Girl.”
I don’t know if her behavior is stemming from your muddled friend-roommate-lover relationship or if she would behave this way under platonic circumstances. But regardless, make no mistake, you are in a relationship. A pretty toxic one at that. Even though you may call it a hookup, those are still relationships—short ones, usually, but relationships, nonetheless.
She’s taking advantage of your generosity (and probably your feelings for her) and it’s time to stop letting that happen. No more bankrolling trips. No more sex. Also, you should ask her to pay the rent she owes. Or get the landlord involved if you don’t want to be the enforcer. But don’t continue to pay her rent because you’re afraid to confront her.
It seems like you should ask her to move out as well. Can you do so legally? Depending on whether she’s on the lease or not, you may be able to evict her for not paying rent. Consult the Illinois Tenant Handbook to find out your rights as a renter.
But before you do that, it’s time to sack up and have an honest, awkward, face-to-face conversation about the entire situation. You can even start with, “Hey, things have felt really awkward lately. Is anything going on that you want to talk about?”
Then segue into how this living situation is not boding well for either of you, and she probably feels the strain, too. Tell her you care about her, but it also seems clear you and she are not a good match as roommates, and she should find another place. You can even offer to help her find a new place if you’re feeling generous. (You’re not obligated, however.) Try to be as amicable as possible, but don’t let your fear (or your desire) stop you from making healthy living choices.
Then, next time, don’t bang your roommate. Even if you “want to help” her rebound from a crappy relationship.
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Good luck, RD!
Anna Pulley is a RedEye contributor. Want to ask Anna an anonymous question about love, sex or dating? Send it below, or email [email protected].