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Hooksexup Endings: Male, 25, Portland

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First in a new series of breakup stories. "I showed her the couch and hinted she should sleep on it…"

Male • 25 • Portland, ME

Hooksexup Endings is a new biweekly series of reader-submitted breakup stories.

I was dating a girl named Emily, and she was a bit of a crier. As in, when another driver flipped her off when she was changing lanes, it was like, waterworks. Our relationship wasn't going very well, and she was taking a month-long writing fellowship in the U.K. I was staying in Portland, and I told her we should use the time to think about stuff. By this, I meant we should consider ourselves broken up while she was away. In retrospect, maybe I could've been clearer about that. Anyway, a few days before she got back, I hooked up with my friend Amanda, and we started seeing each other.

So when Emily came home, at her welcome-home party, I told her that she should probably stay with another friend until we had a chance to talk. She said yes… but then she came home with me anyway. So (here's another thing I could've been clearer about in retrospect) I kind of showed her the couch and hinted she should sleep on it. Needless to say, after she brushed her teeth and I got in bed, she came into my room and took her clothes off and got in bed with me.

Somehow, I resisted temptation and told her we couldn't hook up. She spent the next seven hours crying in my bed, and then explained to me that she was counting on staying with me for a few weeks when she got back from her trip, until she found a place, and she had nowhere else to stay.

What could I say but yes? So she moved in with me. But I didn't tell her I was dating Amanda. So when I'd leave to hook up with Amanda, I'd literally sneak out of my own house — I'd tell Emily I was going to bed, close the door to my bedroom, wait for her to go to bed, and then tiptoe out the front door. But I felt terrible, because I'd always catch Emily crying in my apartment. So after a couple of weeks, I told her that I was dating Amanda, and she lost it again.

Now the waterworks were running every day, and now she knew where I was running out to when I left at random times. But she still apparently couldn't find a place to stay, and the weeks were turning into months. We were still trying to be friends, and we were still hanging out once or twice a week — and since she was so sensitive, I was routinely cancelling plans with Amanda because I didn't want to hurt Emily's feelings. And while Emily was a big crier, Amanda was a big yeller, and would get furious and hurt every time I cancelled on her (understandably). It enraged her that we could never go to my house because I was terrified of seeing Emily there.

Emily ended up staying with me for three months. It was probably the most sadomasochistic relationship of my life, and we weren't even having sex. She'd do things to torture me, like leave the door open while changing, and she'd occasionally sleep in my bed, but we never hooked up.

Then, while she was still living with me, she started sleeping with the worst person ever — like, my least favorite person in the world. I was so mad about it, even though I obviously had no right to be. Finally, one night I was at a bar with some friends, Emily, and the guy she was dating. When it came time to leave, I watched her silently agonize over who she was going with. The tension was unbearable. I remember her walking away with the other guy and seeing her fighting back tears. As for my relationship with Amanda, it was obviously doomed from the start.

We're looking for stories about memorable breakups. Email  with 300-700 words. (Don't worry, we won't print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.

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