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1985 American adventure comedy romance film by Rob Reiner

High school senior Walter Gibson and his best friend Lance 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 woo the ambitious, pensive Alison Bradbury 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, assuring him she is a "sure thing". Walter finds a ride from a ride share board to make the trip. He meets Gary Cooper and Mary Ann Webster, the couple providing the ride. 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. 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, infuriating Alison. Alison hitches a ride from a middle aged man who swiftly attempts to rape her, but Walter comes to her rescue just in the nick of time. The two decide to stick together, eventually making it to a train station. However, when Walter does not have enough money to cover his bus fare, the two instead check into a motel. Walter grows jealous when he overhears Alison talking to Jason on the phone, and ventures to a nearby bar where he spends his remaining money on alcohol and drunkenly sings Christmas carols with the locals. The next morning, Walter rushes Alison out of the motel, and has her stuff her shirt with scarves so she appears pregnant, hoping it will increase their chances of getting a ride. The two manage to hitchhike to a restaurant, whereupon Alison realizes she left her appointment book and cash back at the motel. That night, the two are crestfallen when they find themselves caught outside in a rainstorm, until Alison realizes that she has her father's emergency credit card. The two use the credit card to stay at an upscale hotel, where they treat themselves to drinks and dinner. The next morning, Alison is pleased to find Walter embracing her, but he quickly pulls away upon waking up. While hitchhiking with a truck driver through Arizona, Alison overhears Walter explaining that he made the trip to meet his "sure thing". Upon arriving at the UCLA campus, Alison angrily parts ways with Walter. That night, Walter attends a Christmas mixer where Lance has arranged for Walter to meet his "sure thing". Meanwhile, Alison finds herself bored at Jason's dormitory, and decides to drag him to the same party. Alison and Walter see each other, but their mutual jealousy leads to a confrontation between the two. Walter takes the "sure thing" to Lance's room, but cannot stop thinking about Alison. Back on campus after Christmas break, Alison and Walter are obviously uncomfortable around each other. In their English class, Professor Taub reads an essay composed by Walter as a writing assignment, which is a description of 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, she tells Walter that she and Jason broke up, and they kiss.

The origins of the film came from an experience writer Steven L. Bloom had while attending Brown University.

When casting for the part of Walter Gibson began, director Rob Reiner initially refused to meet with John Cusack because the actor was under aged. Casting directors Jane Jenkins and Janet Hirshenson convinced Reiner to audition Cusack, after which Reiner knew he had to have him for the part. At the time Anthony Edwards was seriously being considered for the lead, but after Cusack got the part, Edwards was offered the best friend role instead. At the time of his casting, Cusack was still 16 and had not yet graduated from high school, so producer Roger Birnbaum had to go to court to have him emancipated. During the filming of the movie (March–April 1984), Birnbaum then became Cusack's legal guardian.

The Sure Thing was given advanced sneak previews in the United States and Canada on February 23, 1985 before its wide release on March 1, 1985.

Reviews for The Sure Thing were mostly positive. Film critic Roger Ebert, who gave it three and a half stars out of four, praised the film and called it a "small miracle" for its handling of teenage material in an era when movies like Porky's were the norm. In a review for The New York Times, Janet Maslin wrote that The Sure Thing was "glowing proof of two things: Traditional romantic comedy can be adapted to suit the teen age trade, and Mr. Reiner's contribution to This Is Spinal Tap was more than a matter of humor". Variety deemed the film "a sweetly old fashioned look at the last lap of the coming of age ordeal in which the sure thing becomes less important than the real thing. Realization may not be earth shattering, but in an era of fast food and faster sex, return to the traditional is downright refreshing." Time Out magazine described the film favorably as a "confident, witty teenage variation on It Happened One Night [that] focuses on two students hitching across the States through rainstorms, starvation and show tunes. He's a libidinous layabout who inadvertently dropped in to college. She's an uptight goody goody who believes spontaneity has its time and its place. There's plenty of mileage in this pairing, even if the movie isn't going anywhere unexpected." In 2017, the British Film Institute ranked The Sure Thing among Reiner's five most essential directorial efforts, noting: "In an age when American teen comedies came to be defined by the success of Porky's (1982), The Sure Thing triumphs from its winning formula of being sassy yet never bawdy and sentimental while never mawkish." The film holds a rating of on Rotten Tomatoes based on reviews. The website's critical consensus reads: "Though its final outcome is predictable, The Sure Thing is a charming, smartly written, and mature teen comedy featuring a breakout role for John Cusack."

MGM Home Entertainment released The Sure Thing in a special edition region 1 DVD on August 5, 2003. In 2015, Shout! Factory released a 30th anniversary Blu ray edition of the film. Sandpiper Pictures reissued a Blu ray edition on December 19, 2023.