Anyone know the movie where...

The movie is similar to American Pie so I'm asking it here, not sure where else to ask it. It was a movie where a teenage guy made it his goal to get this girl by the end of summer (it may have been the end of school, but I think it was the end of summer). She had a boyfriend where it was later revealed he stuffed socks into his underwear. It may have been a B movie, because I don't know who starred in the movie (so I can't look that up). It may be a TV movie, but I don't think so, it had quite a bit of sexual references iirc. I tried a google search, but I don't remember enough about the movie to narrow it down. The socks in the underwear bit is the most memorable part in the movie. It seemed like a B movie (although I may be mistaken), but I kind of enjoyed it and wouldn't mind watching it again. It's driving me crazy I never found out what the movie was (since I missed the beginning and the end). Any help would be vastly appreciated.