Valentine (2001)

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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.