The Sure Thing
A sure thing comes once in a lifetime... but the real thing lasts forever.
Gib, a beer-guzzling slob, and Alison, an uptight Ivy-Leaguer, are an unlikely duo stuck together on a cross-country trip during Christmas break. At first they get on each other's nerves but, as time passes, they find their divergent natures complement each other. Now they need to realize what they've already found before it's too late.
High school senior Walter Gibson (John Cusack) and his best friend Lance (Anthony Edwards) are celebrating the fact they are moving on to college, but all Walter can do is lament the fact that he has lost his touch with women. Lance heads to UCLA while Walter moves on to college in New England. The two keep in touch by writing letters, but Walter’s luck has not changed. His attempt to get close to Alison Bradbury (Daphne Zuniga) from his English class by tricking her into tutoring him only results in his angering and alienating her. Eventually he receives a phone call from Lance telling him to come to California for Christmas break because he has set him up with a beautiful girl (Nicollette Sheridan), assuring him she is a Sure Thing.
Walter finds a ride from a ride share board to make the trip. He meets Gary Cooper (Tim Robbins) and Mary Ann Webster (Lisa Jane Persky), the couple providing the ride: they are extroverted and upbeat to a fault. Things go from bad to worse when he realizes he will be sitting next to Alison as she heads to UCLA to visit her boyfriend Jason (Boyd Gaines). The tension and bickering between Walter and Alison becomes too much for Cooper, and he abandons them on the side of the road in the middle of nowhere and Alison hitches a ride which turns out to be a big mistake. The driver stops at a deserted little pocket of the road and attempts to rape her, but Walter comes to her rescue just in the nick of time. As they hitch to California, they overcome issues with transportation, weather, lack of food, lack of money (caused by Alison leaving her wallet behind) and sleeping arrangements, while at the same time developing genuine feelings for one another. Upon arriving in California, Alison discovers the real reason Walter made the trip is to meet his “Sure Thing” and angrily walks away.
That night at a college mixer Lance has arranged for Walter to meet his “Sure Thing”. Meanwhile, Alison is spending a boring night with Jason when she drags him to the same mixer for some fun. Alison and Walter see each other at the party, but jealousy leads to a confrontation between the two. Walter takes the “Sure Thing” to Lance’s room, but cannot stop thinking about Alison…