Movies like Head Over Heels

This comedy starring Kate Hudson and Matthew McConaughey follows a journalist writing an article on how to drive a man away, but real feelings emerge. Its mix of romantic hijinks and a bet-gone-wrong offers similar charm to Head Over He Heels.

Reese Witherspoon stars as a New York fashion designer who must confront her past in Alabama. The film showcases a humorous clash of worlds and rediscovery of first love that fans of Head Over Heels are likely to enjoy.

Reese Witherspoon's character turns stereotypes on their head when she enrolls in Harvard Law School to win back her ex-boyfriend. Much like Head Over Heels, it combines humor with an empowered female lead navigating love and professional aspirations.

Jennifer Garner stars in this romantic comedy about a 13-year-old girl who suddenly finds herself in the body of a 30-year-old. The magical elements and the challenge of new-found adulthood align with the whimsy and romance of Head Over Heels.

Sandra Bullock stars as an undercover FBI agent entering a beauty pageant. This film pairs physical comedy with a transformative love story, capturing a vibe akin to the quirky and unexpected romance in Head Over Heels.

Starring Jennifer Lopez, Maid in Manhattan offers a modern-day Cinderella story set in New York, where a hotel maid falls for a wealthy politician. Its blend of romance and class-crossed lovers echoes the themes of unforeseen love found in Head Over Heels.

The Wedding Planner features Jennifer Lopez as a successful wedding planner who unexpectedly falls in love with a groom-to-be. Much like Head Over Heels, it combines romantic entanglements with a light-hearted approach to love and career.

In Just Like Heaven, Reese Witherspoon plays a spirit who can't remember her past, which leads to romantic and comical situations with the current tenant of her apartment. It shares the blend of supernatural happenings with heartfelt romance found in Head Over Heels.