Desperately searching for movie title!!

[diceroller1978]

I'm looking for a movie that came out around the late 90's, early 2000's. It was a comedy about a guy who ran into a bunch of former high school classmates like 10 years after he graduated. Kind of a nerdy white guy with shaggy brown hair and glasses. One of the people he runs into is a girl he had a crush on who ends up becoming an exotic dancer. He goes to watch her perform at the strip club and she dances to Blondie, "Heart of Glass." It was on HBO pretty much everyday for about a year. Can't remember the title and it's driving me crazy!! Lol.

 

[mal3volent]

http://www.imdb.com/name/nm1341522/

 

[Matrioshka Brain]

I did some searching without any useful results; this one has me stumped.