Why Does The Guy I'm Dating Get Along Better With My Roommate Than Me? Ask A Pro

By The Head Pro

Dear Head Pro,

Met a nice guy online, very sweet, very nice, very cute.  We went out for dinner twice, third and fourth dates he cooked at his house and sex was involved. Fifth date was just a sleepover. Never heard from him again (it's been more than a week). I'm ok with it and I was ready for these steps but I just wish I had had more time to get to know him better. I liked a lot of what I saw and just enjoyed his company. IF he does approach me again, I just wish I could know the things to do to get to know him better and not have things fizzle out. 

I cannot reach out to him because I already initiated the last time. I don't want to force something that isn’t working. I just want to make sure that I learn from this and that if he does come around, I am able to keep an even keel while we get to know each other better. Who only wants to go on 5 dates and start over time after time? Not me.

Dear Nameless,

Well, this is a very weird email. Like, how was sex “involved” in the cooking at his house? Did you two have sex? Did he make a sexy dish, like steak au poivre or Chick Fil A takeout? Did he make an otherwise benign meal in a very sexy way, gyrating his hips to the music while chopping onions, totally nude save for an apron, chef’s hat and Crocs? Dammit, now I really want to know.

Anyhow, I’m not exactly sure of what you’re asking. You seem like you have a very automated, punch-card approach to relationships (Dear Head Pro, please delineate all possible permutations when combining variables X, B and R), which is its own problem. But in this situation, I don’t understand the question. You’re saying you hung out with the guy multiple times and that things fizzled abruptly. You say you’re ok with that, but also want to know how to do things differently should he text you back before the heat death of the Earth. Why? It’s pretty clear he won’t. If he did, why would you want him back?

I think you’re saying you must have screwed up somewhere along the way, which is false. When it comes to getting to know someone, you did about all there is to do - you hung out together. Sure, people generally wait several dates before allowing a guy to cook them clams casino in the nude for purposes of getting to know him more fully first, but that’s a minor issue. In the future, opt for dates that are more about sharing experiences than they are meals. That’s how you get to know someone’s insides before allowing them inside. Otherwise, welcome to the dating game, where more often than not, things just don’t work out.

The point of online dating is having multiple chances to start anew,

Head Pro

Dear Head Pro,

I started dating this guy I met online and I invited him to my apartment to hang out one night when my roommate was around. I'm not super into the guy (we don't have a lot in common) but I wanted to see if he could get along with my friends. So he comes over to make me dinner and next thing I know he is talking sports, music, tv shows and everything else he happens to have in common with my roommate! I was the one who felt like the third wheel. My roommate even made a movie reference that I didn't get, but this guy picked up on immediately. Later in the evening I made a joke about how he should date my roommate and he immediately went into this spiel about how he isn't interested in her at all, she is a cool girl but they only get along because she is "just one of the guys."

It has been about a month and every time he is over when my roommate is around I end up feeling out of place. He assures me that he only has eyes for me and he likes that we have other things to talk about besides sports, since he can do that with his guy friends. The issue: we really don't have much more to talk about. Now I am considering breaking it off but my roommate keeps asking about him and will ask me when he is coming over next. I feel like a jackass for not being interested in him and, double whammy, for taking away this new flourishing friendship from my roommate. I honestly think that my roommate should date this guy to the point where I don't even think it would be weird. How do I break up with a guy and make the subtle (or not so subtle) suggestion that my roommate is a much better match? (Is that super fu**ed up?)


3rd wheeling my own relationship

Dear 3rd Wheel,

This one actually made me laugh. Like, how have you managed to continue dating someone for whom you have essentially zero interest for over a month now? That’s absurd to me. I have, on occasion, cut things off mid-date if I didn’t think it was going anywhere. Hopefully, you’re not holding on to the relationship for your roommate’s sake, as you are not the steward of her social wellbeing. In fact, your problem becomes easier the better you’re able to separate your dealings with from whatever might exist between the two of them.

If you have little in common with the guy and on top of that you feel like a stranger in your own home when he’s with your roommate, then fucking break up with him. It’s that simple. It’s not like you’ll miss him, after all. Again, don’t mince over how it might affect your roommate - she’s not the one dating him, and you not dating him ostensibly doesn’t prevent her from being friends (or whatever else) with him. If you really want to cover your ass, be honest and clear to both of them when they ask if it had anything to do with their dynamic (you know they’ll ask). Just keep it about you - you had nothing in common with him.

If the two of them really do get on so well together, I promise you they’ll find a way to bridge the gap between them that you once occupied. They are adults; they don’t need you to hold their hands. Just make sure you aren’t actively standing in their way (and maybe help them exchange numbers, if you really insist on playing matchmaker), and let them figure it out.

Roommate Kisses,

Head Pro

Got a burning question? Email The Head Pro at [email protected] and follow him on Twitter here.




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