Movies like How to Lose a Guy in 10 Days

In 27 Dresses, Katherine Heigl plays a woman who's always the bridesmaid and never the bride until her sister captures the heart of her secret crush. Similar to How to Lose a Guy in 10 Days, the film combines the elements of unrequited love, family dynamics, and the central theme of self-discovery in a romantic context, all with a light-hearted tone.

The Proposal, featuring Sandra Bullock and Ryan Reynolds, is a romantic comedy about a pushy boss who forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation. Fans of How to Lose a Guy in 10 Days will appreciate the clever humor and the chemistry between the leads, as well as the unexpected emotional depth as the pretend relationship becomes real.

Bride Wars is a comedy starring Kate Hudson and Anne Hathaway as two best friends who turn into rivals when their weddings are mistakenly scheduled on the same day. It captures the spirit of competition and the themes of friendship and love, similar to the rivalry and romantic tension in How to Lose a Guy in 10 Days.

Sweet Home Alabama follows Reese Witherspoon's character, who must confront her past and choose between a glamorous New York lifestyle or returning to her roots in Alabama. This romantic comedy shares with How to Lose a Guy in 10 Days a strong-willed protagonist and a story that revolves around love, choice, and the journey back to oneself.

The Ugly Truth features Katherine Heigl as a morning show producer who is reluctantly embroiled in a series of tests by her chauvinistic correspondent to prove his theories on relationships. Like How to Lose a Guy in 10 Days, it's a battle-of-the-sexes comedy that explores modern love and gender stereotypes with a humorous angle.

Maid in Manhattan stars Jennifer Lopez as a hotel maid who falls for a wealthy politician while masquerading as a socialite. Those who like How to Lose a Guy in 10 Days will enjoy the themes of mistaken identity and class-crossing romance, complemented by strong performances and a charming narrative.

Failure to Launch stars Matthew McConaughey, who also starred in How to Lose a Guy in 10 Days, as a 35-year-old still living with his parents. The film's combination of romantic entanglements and family dynamics, along with a similar comedic tone, makes it a fitting recommendation for audiences who enjoyed the playful nature of the McConaughey and Hudson pairing.