A past hookup with roommate is causing trouble. What do I do?


highwayrider asks:

I recently started dating a girl who works at a coffee shop down the street. Things escalated quickly one night and she ended up back at my place where things became very intimate and physical, though we didn’t have sex. A few days later, she texts me and says, ”hey, I’m picking up a vibe between you and your female roommate.” I assured her there was nothing there, my roommate and I are just friends and I was not interested in her. The thing is, I did hook up with my roommate a few months ago, but it only lasted for a few weeks and then it ended. I’m not into my roommate at all any more, nor is she into me.

I had lunch with the girl a few days later. She brought up the roommate thing again and so I was straight with her. I told her I wasn’t totally honest with her, my roommate and I had a brief fling a few months back, it’s over, but I’m not interested in her. I told her I really liked her and would like to keep seeing her. The girl didn’t seem too upset about it and said she would still like to “hang out.”

I felt like it was probably over, but she texted me the next morning and we texted all day. We made plans to hang out that night, but when I met up with her, she was really drunk and with some friends and didn’t introduce me to them. I chalked it up to her having too much to drink, but since then, she’s been really distant, and I’m worried I fucked this up pretty bad.

I really like this girl, and I’m really beating myself up pretty hard for ever getting involved with my roommate. Is this girl worth fighting for, or do I need to bow out?

Demetrius says:

Another question, another guy asking if he should choose between 2 options as if they are the only options available. When will you folks ever learn?

Let’s tackle this idea that you either have to fight, or bow out like you’re a goddamn prize-fighter on his last legs. This isn’t some moment of heroic decision between fighting for the one you love or letting her go. Is she worth fighting for? That’s a relative measurement but generally speaking, if people are trying to create distance between you and them because they’ve lost interest, they aren’t worth fighting for. You don’t fight for people who aren’t interested in you, you just let them go. You don’t “bow out” like you’re fucking Derek Jeter on his retirement tour, you just let nature take it’s course. In your case, you just need to let nature take it’s course. No grand gesture, no official ending, just work on meeting someone new because you’re about to be dropped.

More importantly though, you shouldn’t be beating yourself up about your past hookups with your roommate. They happened, it happens, and it seems like you’ve both moved on. Maybe the coffee shop girl noticed some underlying sexual tension between you two, because there’s always sexual tension when you’ve slept with someone, but it seems like that’s only one of the many reasons why this girl would have ended things. You showed up to a date with her and she was already drunk so maybe that’s your problem rather than the time you hooked up with an ex. Maybe she was always going to lose interest, or maybe she’d find out about some other girl from your past and be upset about that. Who knows? What I do know is that whether she recognized the tension or not, it’s not like you’re a bad person for hooking up with your roommate. Bad decision-making? Sure, absolutely. But it doesn’t make you a bad person, even if that hook up did contribute to things with coffee shop girl ending. It wasn’t the fact that you hooked up with the roommate though, it was your dishonesty about it.

In the future, when someone asks about your roommate, or if you’ve been with someone else, be honest about it then and there. Since you’re about to get dumped (or more likely, Ghosted) you’ll have plenty of time to figure out your talking points for how you’ll explain to the next girl the situation with your roommate. “We’ve hooked up, never dated, it was a few months ago, we haven’t hooked up since then, and I’m not interested in dating her” are all great points, especially if they’re all true. Your major misstep in this situation had to be when you were dishonest and then followed it up with honesty. Next time, just lead with the honesty.You’d think that dishonesty, followed by honesty, would win you some points, but it doesn’t. It usually comes off as a guilty act, rather than a redemptive act. I’m sure it was the dishonesty, rather than the fact that you hooked up with your roommate that contributed to coffee shop girl losing interest. .

Just remember, honesty is the best policy. Or dishonesty. Just stick with one or the other next time.

Good Luck Out There.

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