Unrequited love has been a timeless theme in cinema, often blending humor with heartache. This curated list of 10 comedy films explores the lighter side of love that goes unreturned, providing both entertainment and a touch of empathy. These movies not only offer a good laugh but also resonate with anyone who has experienced the bittersweet pangs of one-sided affection. Whether you're in the mood for a romantic comedy or just need a dose of humor, these films are sure to entertain and perhaps even heal a little bit of your heart.

Clueless (1995)
Description: Cher Horowitz's attempts to play matchmaker for her teachers lead to her own realization of unrequited feelings for her ex-stepbrother, Josh, providing both laughs and lessons in love.
Fact: The film is loosely based on Jane Austen's "Emma," with Cher embodying the matchmaking spirit of the novel's protagonist.


Love Actually (2003)
Description: While not solely about unrequited love, this film features multiple storylines, including the story of Mark, who harbors secret feelings for his best friend's wife, showcasing the humor and sadness of unreturned affection.
Fact: The film includes a scene where Hugh Grant dances to "Jump (For My Love)" by The Pointer Sisters, which was improvised on the day of shooting.


Along Came Polly (2004)
Description: Reuben Feffer's attempt to move on from his ex-wife leads him to Polly, but his lingering feelings for his ex-wife create humorous situations, highlighting the theme of unrequited love.
Fact: The film features a scene where Ben Stiller's character tries to eat a spicy chicken wing, which was improvised and led to genuine reactions from the cast.


Scott Pilgrim vs. the World (2010)
Description: Scott Pilgrim must defeat Ramona Flowers' seven evil exes to win her heart, but his journey is filled with comedic mishaps and the realization that love isn't always straightforward.
Fact: The film uses video game-inspired graphics and effects, reflecting the comic book origin of the story.


The Break-Up (2006)
Description: While focusing on a couple post-breakup, it includes moments where characters grapple with lingering feelings, showcasing the comedic side of trying to move on.
Fact: The film was originally conceived as a more dramatic piece but was rewritten to include more humor.


The Holiday (2006)
Description: While primarily a romantic comedy, it includes a subplot where Iris Simpkins deals with her unrequited love for Jasper Bloom, adding depth to the film's comedic elements.
Fact: The film features a memorable scene where Iris watches "It's a Wonderful Life" and cries, which was improvised by Kate Winslet.


She's Out of My League (2010)
Description: Kirk Kettner's relationship with Molly, who seems out of his league, is filled with comedic moments as he navigates his insecurities and her ex-boyfriend's interference.
Fact: The film was partly inspired by the real-life relationship of one of its producers.


He's Just Not That Into You (2009)
Description: This ensemble comedy-drama explores various relationships, including Gigi's persistent pursuit of a man who clearly isn't interested, highlighting the comedic aspects of unrequited love.
Fact: The film was inspired by a self-help book of the same name, which was based on a segment from "Sex and the City."


500 Days of Summer (2009)
Description: This film follows Tom Hansen as he navigates the ups and downs of his relationship with Summer Finn, who doesn't reciprocate his feelings in the way he hopes. It's a perfect blend of comedy and introspection on love's complexities.
Fact: The film uses a non-linear narrative to reflect the emotional rollercoaster of unrequited love. The movie was inspired by director Marc Webb's own experiences with love.


Crazy, Stupid, Love (2011)
Description: The film features multiple storylines, including one where Cal's son, Robbie, has an unrequited crush on his babysitter, Jessica, leading to humorous and touching moments.
Fact: The film's title is a play on the phrase "crazy, stupid, love," which encapsulates the various forms of love depicted in the movie.
