Christine Ramsay (played by Phoebe Cates) is a young girl who is going to an all-girls private school. She is in love with Jim Green (played by Matthew Modine), who also is going to a private school, an all-boys school near by. Christine has to deal with her rival, Jordan Leigh (played by Betsy Russell), who has the hots for Jim. Jim's uber-slob friend, Bubba Beauregard (played by Michael Zorek), is going out with Betsy, a good friend of Christine's. Betsy (played by Kathleen Wilhoite), thinks that Jim would cheat on Christine when he is around a lot of other girls. Bubba and his pals go over to the girl's school and dress in drag to get inside and see the Promised Land, also known as the girl's shower room. Christine and Jim decide to go out and have a weekend that will be romantic, but things don't go well as they had planned.

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