The Sure Thing

A Romantic Comedy that's suspiciously similar to It Happened One Night. It's a Road Movie, in The Eighties, WITH TEENAGERS!

Walter "Gib" Gibson is just an 18-year-old Cool Loser trying to get laid and trolling on the Brainy Brunette (Allison) in his English class. It's not going well. Then his best friend going to college in Los Angeles sends him a picture of a hot blonde, with the assurance that she's "a sure thing." If Gib can make it out to LA for winter break before "the sure thing" goes off for a semester at sea, he can totally bag that.

Gib goes along on a rideshare, only it turns out that Allison's going to LA to visit her boyfriend too...

Tropes used in The Sure Thing include:

Attempted Rape: the cowboy hitchhiker who picks up Allison.
Beergasm
California Doubling: most of the East Coast college scenes (the ones without snow) were filmed at University of the Pacific.
Cool Teacher: Professor Taub
Dawson Casting: averted with John Cusack, who wasn't even 18 yet.
Did I Mention It's Christmas?: Everyone is still at college partying on December 22 or so? And nobody's parents are demanding to see them for the holidays?
Did They or Didn't They?: Gib and "the sure thing", revealed at the end when they're back at school.
Disney Theme Parks: At one point Allison wants to go to Disneyland, only to be brutally rebuffed with "Disneyland is for children."
Disposable Boyfriend: Jason, who's a total nerd and hates all fun.
Exact Eavesdropping: in the cab
Flyover Country: Director Rob Reiner went to UCLA; writers Steven Bloom and Jonathan Roberts went to Brown. The scenes in the unnamed New England Ivy League-type college and at UCLA are very sharply detailed. The 3000 miles between, in contrast, are in good old generic America.
Improv: John Cusack did a lot of this in the movie, according to the commentary/trivia tracks. Especially any scene involving beer.
Kavorka Man: Gil's roommate Jimbo is very skilled at getting the ladies.
Left Your Lifesaver Behind: When Gib and Allison leave the hotel room, Allison accidentally leaves her all-important planner (which contains all her money) behind.
Love Before First Sight: Gib having the hots for (if not being in love with) "the sure thing" just from her photo. Also Girl of My Dreams, though for the realistic reason of him having seen her photo first. And in the end he doesn't end up with her.
A Man Is Not a Virgin: And Gib is very offended when he's mistaken for one.
Mistaken for Cheating: Allison, who didn't, but you could reasonably guess by what she says about Gib's sleeping habits that she did.
Mistaken for Gay: Gib, since Lance told "the sure thing" he was a virgin and probably this too.
Nice Hat: Professor Taub is always wearing hers.
No Name Given: "the sure thing."
Pillow Pregnancy: Allison fakes one to get a ride.
Playboy: Jimbo writes a "I never thought this would happen to me" letter, which Gib mistakenly grabs and turns in as his English homework. Naturally, it's read in front of the class.
- It's actually Penthouse (which had the racy letters pages), but close enough).
Road Trip Romance: The plot is based off of the Trope Maker; It Happened One Night.
Sex as Rite-of-Passage: Gib isn't a virgin, but his goal in life is to get laid some more.
This Is My Side: played straight at first and then later relaxed quite a bit.
Uptight Loves Wild
Wild Teen Party