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College freshman Walter "Gib" Gibson (John Cusack) has a "sure thing“ date with a very hot and very sex-craved blonde across the country in LA. Crossed by fate—and the ride-share bulletin board—Gib makes the trip with a studious and abrasive coed (Daphne Zuniga). But as they overcome every obstacle, from show-tune-singing simpletons and bad weather to leering truck drivers and worse luck, their temperaments change and Gib realizes that the only sure thing is that losing the real thing would be the worst thing of all!