Valentine's Day 1988: At the school dance, geeky Jeremy Melton bravely faces one rejection after the other when asking four popular girls to dance with him. A fifth girl, plump and insecure, agrees, but they end up making out under the bleachers. When a group of school bullies catches them, the girl claims that Jeremy attacked her. This causes them to strip off his clothes and beat him up in front of the entire school. Flash forward to 2001. We meet the five girls who were in that school gym: Kate, Paige, Shelly, Lily and the formerly plump Dorothy. They are all in their 20's now and trying to sort out their love lives, which is appropriate, since Valentine's Day is coming up. After a disastrous date with a loser, one of the girls, a pre-med student, is murdered by a Cherub-mask wearing killer who sent her a death threat in the form of a Valentine card prior to the attack...

Van Wilder is a guy who has been at his college for seven years. He spends most of his time throwing parties and "fund raisers". When his father decides that it's time for tough love, he doesn't pay his tuition. So Van becomes a professional party thrower. At the same time, Gwen who writes for the college paper, is tasked with doing a story on him, but Van is too busy partying to do that. So she writes it using info from people who talk about him and writes an unflattering piece, which doesn't make him happy. He then dares her to see if she can get the true story but is more interested in trying to score with her, which is not easy because she has a boyfriend, who is a snob, and who is not too happy with the amount time she is spending with him. So he tries to get rid of him.