I watched Swingers again the other day, and it reminded me of something that happened while I was in undergrad...
There was a guy in my fraternity named Brent. He was in my pledge class, and no one in the class could figure out why he recieved a bid, because he didn't fit in at all. We later learned that his parents were close friends with the parents of the Rush chair, and it was a total sympathy bid. He basically recieved a pass through the pledgeship as well and was initiated in as an active member.
Part of Brent's problem was that he was really insecure about his place in the fraternity. He was always really worried what everybody thought of him and was one of those guys who tried way too hard. Usually, each year there is one 'Brent', and those guys always carved out a niche and became well liked. But Brent was an angry, bitter drunk, and it was very hard to like him on any level.
Nevertheless, he tried very hard to fit in. Brent was not an attractive fellow, and he had a terrible personality, so he never was the recipient of any attention from girls. His encounters were few and far between. Once, when he was wasted, he was describing how he lost his virgininty as a drunken freshman, and someone asked how big the girl was. He looked around the room, pointed to me, and said "About Mike's size." (Note: I am six feet tall, weigh 220, and am built like a fullback....yeah....{shudder}...)
But around the middle of the first semester of our sophomore year, a freshman girl named Mary seemingly had a thing for Brent. This girl was the very definition of average, both in looks and personality. She hung around the frat house because her prettier and cooler roommate was dating a guy in the house. Wanting to have a boyfriend in the house too, this girl locked on to the surest thing, Brent, and they began casually seeing eachother, and Brent asked her to our annual semi-formal.
However, Brent was still insecure about himself, this time because his girlfriend wasn't as pretty as the girls other guys were dating. We were all supportive, in the sense we never ripped on her. In fact, we were thrilled because he no longer creeped out our girlfriend's friends who came over, or cockblocked anyone, or asked to be set up with a date to a date party or something. But Brent was still insecure about it.
One day, I was sitting in my room with my roommate Chad and our good friend Pat. Brent came in and said he needed to talk about something. He proceeded to tell us that he didn't want to take Mary to semi-formal and he wanted to break up with her. We all strongly encouraged him not to do it, but he couldn't be persuaded. At one point Pat, who didn't ever say too much, but when he did, it was hilarious, said "Dude, you are never going to do any better. You shouldn't be breaking up with her, you should be buying her a fucking engagement ring before she comes to her senses."
But no matter what we said, we couldn't convince him. He said he was going to do it over the phone, and was going to do it right now. Always in the mood to see a trainwreck, I suggested he do it in my room, so we could watch. He said okay, and dialed the phone. It rang a few times, her machine picked up, and he hung up. "Come on Brent, leave her a message", Chad said.
So Brent called back, waited for the machine to pick up, and said, "Mary, it's Brent, call me, I need to talk to you about something important." He hung up, and I said, jokingly, "Brent, you can't leave a message like that. You should at least tell her what you want to talk to her about." To my surprise, he hit redial, waited for the machine to pick up, and said "Mary, it's Brent again, the thing I want to talk to you about is semi-formal. Call me."
At this point, Pat, who had a night class with Brent that evening, said, jokingly, "You should call back and tell her what time to call, since you won't be around later". Brent then hit redial, waited for the machine to pick up, and said "Hey, it's Brent again....ummm, when you call to talk about semi-formal, call before 6 or after 9. Bye." At this point Chad looked at him, laughing so hard that he had tears in his eyes, and said "Dude, you have derailed. You might as well just call her and break up over the machine." Brent started to dial, and I told him to stop. I faced a dilemma...On one hand, part of me wanted to save this girl the embarassment of being dumped by Brent on the answering machine. On the other hand, I wanted to see the trainwreck. I thought for a second, and said, "Brent....be sure to tell her 'it's not you, it's me'".
He hit redial, and we sat on the edge of our seats. The machine picked up, and Brent started talking: "Mary, it's me...ummm...I don't think we should see eachother any more. And I don't think we should go to semi-formal...ummm....". At this point, I got his attention and motioned with my hand to say my line. "Oh yeah, it's not you, it's me. Ummmm...Bye." We all absolutely died.
After a few minutes of hysterical laughter, we stopped, and Brent looked at us and said, "Hey, can you guys find me a date for semi-formal?"