Set in 1985, Adam Sandler plays a nice guy with a broken heart who's stuck in one of the most romantic jobs in the world, a wedding singer. He loses all hope when he is abandoned at the altar by his fiancé. He meets a young woman named Julia (Drew Barrymore), who enlists his help to plan her wedding. He falls in love with her and must win her over before she gets married.

Baby (Jennifer Grey) is one listless summer away from the Peace Corps. Hoping to enjoy her youth while it lasts, she's disappointed when her summer plans deposit her at a sleepy resort in the Catskills with her parents. Her luck turns around, however, when the resort's dance instructor, Johnny (Patrick Swayze), enlists Baby as his new partner, and the two fall in love. Baby's father forbids her from seeing Johnny, but she's determined to help him perform the last big dance of the summer.

When Terry Griffith (Joyce Hyser) loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy (Billy Jacoby), helps her pass as a guy so well that she is soon making friends with the boys at school, including the attractive Rick (Clayton Rohner), who becomes her new best friend. But her gender-swapping makes things difficult when she falls in love with him.