My last serious relationship was with a girl who had lived with her boyfriend for two years when we met. She had dropped everything–family, friends, enrollment at one of the best music schools in the South–to fly out here and start a new life with him. They met on World of Warcraft; after a while she stopped playing but he got more and more involved, to the point where he was neglecting her badly and she couldn’t do anything to take his attention away from the game. This was where I came in. I showered her with affection and visibly enjoyed every minute I spent with her. (There was one period of three days in particular where she stayed at my place every night and we spent every waking and sleeping moment together, and she told me the next week that those three days were the only time she’d ever felt like she didn’t need to wear makeup to be appreciated. To this day that’s the best compliment I’ve ever received.) I so swept her off her feet that she finally decided to dump him for me.
She finally worked up the nerve to bury the hatchet after spending a wonderful week at my place, and that Saturday she went home to break the bad news to her little soldier boy. He cried his big Army heart out and told her how much he loved her and how sorry he was for what he’d done and he promised to change; she cried, then he cried some more, and they were officially back together. I was heartbroken, but determined to keep my cool, and I swept her off her feet again the next week. Wash, rinse, repeat, every week for about a month and a half. By the end of that period I ran completely out of cool–I’m convinced that even Samuel L. Jackson could only keep that up for so long-- and I broke down in front of her, and then she took me back and dumped the other guy. When she broke the news to him again that weekend, she stood her ground and he kicked her out of their apartment. She packed up all her essentials and called me in a terrible weeping state, and I rushed to his place like lightning to pick her, her bags and her cats up. She lived with me for all of 12 hours. The next morning he called her and begged her forgiveness, and she took him back again and moved back in with him.
She went back and forth a handful more times. Finally her sense of obligation to him won. (In the interest of full disclosure, I became less cool and more abrasive and argumentative as this debacle went on.) She had moved in again at some point during this whole adventure. By the time my lease ran out, she insisted on sleeping on the couch when she wasn’t staying over at his place. Finally she dumped me off on her coworker’s empty room; that guy, now my roommate, and I believe that she pretended to patch up their bitterly destroyed friendship for as long as it took to get me a deal on the room, fully intending not to spend any more time with either of us than she had to after that. I was a clingy, sobbing mess at this point, and as she grew more distant I proceeded to cling ever harder. She stood me up 3-5 times a week.
The breaking point came when she–a veterinary assistant who talked about how much she loved animals 24/7–promised to help me babysit my parents’ cat, who had badly burned his paws, while they were out of town. After telling me for weeks that she would be there the whole time to help me give the cat his medicine and do all the required maintenance, she left me hanging. She showed up for an hour a couple of days in and left as quickly as possible. At the same time, another girl (who I had no interest in whatsoever) continually attempted to seduce me, and finally I gave in and we had awful, awful sex. I mean, she was bad. I had to fake my orgasm about once every three times with her, and I’d never failed to come during intercourse before (except once when I was high on meth). We had a lot of sex, and though I’d stressed the noncommittal nature of our friends-with-benefits status going in, she became more and more attached to me. The sex really helped me get over the girl I’d loved and lost, by reaffirming my attractiveness and sexual prowess (she had multiple screaming orgasms while I was trying to stay awake–horribly one-sided, but a great ego boost), but I found the girl irritating and overly clingy, so now I was immediately in the other girl’s shoes. It was hard as hell to shake that girl–she turned into a real creep, showing up at my home and my work and throwing very public tantrums. I had to threaten legal action before she finally got the picture.
Those were my two worst breakups.