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The Sure Thing
High school senior Walter "Gib" Gibson and best friend Lance celebrate moving on to college, though Gib mostly laments having lost his touch with girls. Lance heads to UCLA while Gib attends an Ivy League college in New England. The two friends regularly communicate with Gib saying his luck with girls is unchanged. Gib attempts to woo the ambitious, regimented Alison Bradbury, his English classmate by tricking her into tutoring him. His clumsy seduction angers her.
Lance invites Gib to come to California for Christmas break, saying he can set him up with a beautiful girl, claiming she is a "sure thing" with no strings attached. Gib arranges a cross-country ride share with Gary and Mary Ann only to discover that Alison is also a passenger. She is headed to UCLA to visit her boyfriend, Jason. The tension and bickering between Gib and Alison become too much for Gary and Mary Ann, and they abandon the two roadside in the middle of nowhere, infuriating Alison.
Alison hitches a ride from a middle-aged man driving a pick-up truck. When he attempts to sexually assault her, Gib, who hid in the truck bed, quickly intervenes. The two decide to stick together, eventually making it to a bus station. However, Gib lacks enough money for the fare, so the two instead check into a motel. While Alison is talking to Jason on the phone, Gib leaves and ventures to a nearby bar. He spends his remaining cash on drinks and drunkenly sings Christmas carols with the locals.
The next morning, Gib has Allison stuff her shirt with scarves to appear pregnant, hoping it increases their chances of getting a ride. The two hitchhike to a restaurant, whereupon Alison realizes she left her appointment book and cash back at the motel. That night, the two are caught outside in a rainstorm, until Alison suddenly remembers she has her father's emergency credit card. The two stay at an upscale hotel, where they treat themselves to drinks and dinner. The next morning, Alison is pleased to find Gib embracing her, but he quickly pulls away upon waking up.
While hitchhiking with a truck driver through Arizona, Alison overhears Gib saying that he is on his way to meet a "sure thing". Upon arriving at the UCLA campus, Alison angrily parts ways with Gib. That night, Gib attends a Christmas mixer where Lance introduces Gib to the "sure thing" girl. Meanwhile, Alison is bored staying in Jason's dormitory and drags him to the same party. Alison and Gib see each other, but their mutual jealousy leads to a confrontation. Gib takes the "sure thing" to Lance's room but he can only think about Alison. In Jason's dormitory, Alison tells him about Gib. He asks if she loves Gib and it is implied that she does.
Back on campus after Christmas break, Gib tries making amends with Alison, but she ignores him, angry about the party and believing Gib slept with the “sure thing.” In English class, Professor Taub reads Gib's essay, which describes his night with the "sure thing". The girl in the essay asks the protagonist if he loves her, but for the first time he realizes that those are not just words, and he cannot sleep with her. Alison realizes what actually happened that night and tells Gib that she and Jason broke up. The two reconcile and kiss.