Gib (John Cusack) is a freshman at college and hasn't gotten any since junior year of high school (poor boy *eye roll*). Under the disguise of asking for help with English (which he is failing even though it is his mother tongue), he asks Alison (Daphne Zuniga) for help, but she becomes wise to his slimey come on and kicks him (literally) while he's down. They become sworn enemies. Gib's best mate Lance (Anthony Edwards) then sets him up with a Sure Thing (Nicollette Sheridan)... but she is on the other side of the country and he needs to haul his ass to California before Christmas. And so begins the trip from hell as he and Alison, who is visiting her boyfriend and in the carpool also, travel together.
I seriously love this film and it isn't just because of Cusack (back when he was adorable). It is sweet and sarcastic and full of the honesty of hormones. Plus it doesn't shame anyone for wanting sex. That is very refreshing. It is something that can still be watched today without it being (too) dated.
Watch this before Say Anything; this is a laugh and will make you smile. The other film will change your perspective on boys, love, and life.