My all time worst isn't really a good story, just the overall feeling of the date. Freshman year at the Y and my buddy reeeeaaallly wanted to go out with a certain girl. He begged me to be his wingman and take her roommate out. They decided to hike the Y. The roommate felt like she was cheating on some guy back home just by being on the date and so really didn't talk the entire time. Of course my buddy and the other girl hit it off and basically disappeared leaving me with 2 hours of pure hell trying to keep myself entertained. Lame story, I know, but it sucked.
Best story and probably 2nd worst date ( 2nd worst only because it technically didn't happen with MY date) actually occurred on a tennis court. Again, I was a wingman and was entertaining a roommate while a friend wooed someone he really liked. The date was doubles tennis which was to be followed by dinner somewhere. I'm not a good tennis player, but the rest of them were. The girl my buddy was with stayed planted at the net and was destroying us all night. So at one point I get a pretty easy shot hit at me and I get one of the beautiful strokes on it where you just know it's got great speed coming off of your racket. It caught net girl by surprise because I hadn't hit one that hard all night, and it caught her flush on the nose. Mind you, I don't have the control to hit someone even if I had wanted to, that's just where it went. You may remember that scene in meet the parents where Greg finally gets a spike in that water volleyball game and smashes the bride to be's nose? Well, I did it 10 years before Ben Stiller ever thought of it. Blood everywhere, immediate swelling, girl hitting the ground crying. Awful, awful moment. Needless to say, the evening was over. No second date for my buddy either.
Best story and probably 2nd worst date ( 2nd worst only because it technically didn't happen with MY date) actually occurred on a tennis court. Again, I was a wingman and was entertaining a roommate while a friend wooed someone he really liked. The date was doubles tennis which was to be followed by dinner somewhere. I'm not a good tennis player, but the rest of them were. The girl my buddy was with stayed planted at the net and was destroying us all night. So at one point I get a pretty easy shot hit at me and I get one of the beautiful strokes on it where you just know it's got great speed coming off of your racket. It caught net girl by surprise because I hadn't hit one that hard all night, and it caught her flush on the nose. Mind you, I don't have the control to hit someone even if I had wanted to, that's just where it went. You may remember that scene in meet the parents where Greg finally gets a spike in that water volleyball game and smashes the bride to be's nose? Well, I did it 10 years before Ben Stiller ever thought of it. Blood everywhere, immediate swelling, girl hitting the ground crying. Awful, awful moment. Needless to say, the evening was over. No second date for my buddy either.
). I can't remember why but I stayed in her car (an old full size van that looked like a pedo van with the plush carpeting) while she jumped out to buy tickets. She comes back to the van and tells me she got tickets for the 10:30 showing. I about died.
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