Movies like The Sure Thing

Directed by John Hughes, Sixteen Candles is a teen comedy-drama that focuses on the angst and excitement of high school life and young love. Fans of The Sure Thing will recognize the humor and relatable teenage milestones.

Starring Tom Cruise as a high-schooler whose parents are away, Risky Business mixes humor with a coming-of-age story that includes a romantic plot. Its blend of wit, charm, and teenage rebellion make it akin to The Sure Thing.

John Cusack stars again in this poignant and witty romantic comedy about an underachieving high school graduate trying to win the love of a class valedictorian before she heads off to college. Like The Sure Thing, Say Anything... combines humor with a heartfelt love story.

This romantic comedy subverts typical gender roles, following a high school journalist who disguises herself as a boy to get a story. It shares The Sure Thing's high school setting and themes of love and identity.

A story of unrequited love and friendship, Some Kind of Wonderful showcases the complexities of teenage relationships, as a young man's best friend, a tomboy, helps him to land his dream girl. Like The Sure Thing, this movie offers a mix of humor and heartfelt emotion.

This 80s teen comedy/drama follows a nerdy high school guy who 'buys' a cheerleader's time to make him popular, but the plan complicates as real feelings emerge. Much like The Sure Thing, Can't Buy Me Love explores themes of love and social status in high school.

A classic 'opposites attract' love story set in the early 1980s, Valley Girl pairs a Valley girl with a punk from the city, navigating the social pressures of high school romance. It shares The Sure Thing's humorous take on young love and the barriers it must overcome.