Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

Am I Looking for Dealbreakers?

So I was on a date late night, another .  Cute in a unassuming way, charming, a little geekly, a little edgy – all good things.  He’s 45 and has a grown up job that he seems to enjoy but that doesn’t define him.  We were having fun talking about silly things and the election and were able to disagree without it getting contentious – again, all good things.

And then he let it drop – the phrase that would change my whole opinion of him, “my roommate”.  Now let’s be clear, I have a pretty high tolerance for starving artists.  If things are tight because you’re chasing your dreams (still) and you don’t want to be trapped in a job that you hate, I can respect that.  I’ve dated guys with roommates before, and it was always a matter of economics. But from everything I could tell with this one, it wasn’t about money.  It seemed to be because, gasp, he liked having a roommate.  The roommate came up as he told me that the two of them were out late the night before, at a bar.
And that, I’m afraid, is a .  While it might be OK for guys in their 20s, or even early 30s to live in packs, herded together like characters in a sitcom or a Judd Apatow movie, I find it repulsive in men of a certain age.
I didn’t go cold on him for the rest of the night.  We continued to have fun (though I had this horrible echo in my head, “roommate, roommate, roommate”) and even kissed a little (and the kiss wasn’t bad, wasn’t fabulous but wasn’t bad) and I would consider going out with him again. But only so that I could find out more about WHY he has a roommate. Because if my suspicions are confirmed and it’s because he likes that eternal adolescent camaraderie from hanging with his friends 24/7 then that will be our last date.
I titled this entry, “Am I Looking for a Dealbreaker?”  Recently, a friend suggested to me that perhaps I’ve gone beyond cautious, beyond defensive in my dating stance.  That my years of dating have led me to a point where I’m just looking for the thing that’s wrong with each guy, looking for each one’s dealbreaker.  I don’t know if that’s true.  I hope not.  I’d like to think I’m not completely closed to the possibility of meeting someone wonderful and that if the right guy came along I’d recognize him and not be looking so hard for his faults that I’d reject him.   Whatever, I don’t think I’m wrong about the roommate thing.  That’s just not cool.

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1 to “Am I Looking for Dealbreakers?”


  1. Dracofly says:

    I totally agree. Its ok at a certain age but soon its better they live alone haha:D