Best movies about unrequited love for Valentine’s Day

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Dating back to ancient Greek tragedy and even earlier, unrequited love is a much exploited trope in Hollywood and has been portrayed in countless films over time, with varying degrees of longevity and success. A one-sided love story has the power to move and touch audiences, as their struggles can often interest, frustrate, and amuse the masses. This style of storytelling is no stranger to the big screen, with some of the most memorable and iconic films embracing this heartbreaking, heartbreaking concept to greater effect than others.


Updated September 23, 2022: If you’re a fan of the unrequited love trope, you’ll be happy to know that this article has been updated with additional content and movies.

Whether it’s the all-consuming love of a literary great, the misguided efforts of a hopeless romantic, or the desperate longing of an unreachable crush, stories of unrequited love have always found a forever home. in Tinsel Town. True love may not be like love in the movies, but since so many people experience the ups and downs of romance, let’s take a look at some of the best movies about unrequited love.

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12 ghost world

Terry Zwigoff’s Critically Acclaimed Dark Comedy ghost world centers on the lives of Enid and Rebecca, two teenage strangers whose once-solid friendship becomes strained when Enid becomes interested in the love life of an older man. Featuring the talented Thora Birch and Scarlett Johansson as a duo and Steve Buscemi as a solitary middle-aged record collector, ghost world is based on the Daniel Clowes comic book of the same name. Enid makes it her mission to help the reclusive Seymour find a wife, but in doing so, she develops a crush on the older man. While not exactly a Valentine’s Day staple, ghost world takes the audience on a journey of self-exploration and perfectly portrays the agonies of teenagers.

11 love in fact

One of the most iconic cinematic depictions of unrequited love, 2003 love in fact follows the lives of eight very different couples one month before Christmas as their stories inadvertently weave together. Mark (Andrew Lincoln) is hopelessly in love with his best friend’s new wife Juliet (Kiera Knightley) and in his efforts to hide his feelings he is shown to be indifferent and seemingly cold towards her. When Juliet attempts to smooth their relationship, Mark is inspired to declare his love to her via a boombox and large cue cards. love in fact has become a modern-day Christmas classic and perfectly captures the heartbreaking realities of unrequited love.

Related: The Best Christmas Movies of the 2000s

ten Welcome to the dollhouse

Todd Solondz’s 1995 cruel coming-of-age comedy Welcome to the dollhouse tells the story of bullied and unpopular 11-year-old Dawn Wiener, a shy girl who constantly feels neglected by her family and friends and tries desperately to stand out and get their attention. When her geeky older brother forms a band and handsome new student Steve Rodgers joins in, Dawn is absolutely in love with the high schooler despite everyone telling her she has no chance with the musician. The lauded indie film depicts Dawn’s growing obsession with Steve and chronicles the embarrassing ups and downs of teenage crushes and unrequited romantic feelings that plague childhood.

9 Gatsby the magnificent

Baz Luhrmann’s maximalist adaptation of F. Scott Fitzgerald’s beloved novel Gatsby the magnificent tells the story of millionaire Jay Gatsby as he meets neighbor Nick Carraway and longs for his former love Daisy Buchanan during the Roaring Twenties. Leonardo DiCaprio and Carey Mulligan portray the hapless lovers, while Tobey Maguire stars as aspiring writer Nick. The heartbreaking love story between Jay and Daisy is infamous and ultimately ends in tragedy, but watching it unfold is a deeply moving experience for audiences. Luhrmann’s typically dazzling interpretation Gatsby the magnificent is a memorable and raw depiction of the ups and downs of love.

8 Pretty in pink

The iconic 1986 teen romantic comedy Pretty in pink tells the story of a love triangle between a girl who must decide between her feelings for her childhood best friend and a wealthy but sensitive actor. 80s darlings Molly Ringwald, Jon Cryer and Andrew McCarthy portray the love trio in the quintessential movie “Brat Pack,” which was written by the beloved John Hughes and directed by A kind of wonderfulis Howard Deutch.

Relatable and down-to-earth, Andie (Ringwald) has a crush on preppy rich kid Blane, and is completely unaware that her best friend and stranger Duckie has been pining for her for years. The original ending actually had Duckie underdog to get the girl, but test audiences booed that ending and Hughes rewrote it so Andie and Blane could get together instead. Sorry, Ducky.

seven The wedding of my best friend

Arguably one of the most popular unrequited love movies of the 90s, the 1997 romantic comedy The wedding of my best friend follows a woman who realizes she’s in love with her best friend after he announces his engagement. She then embarks on a mission to seduce him and tell him how she feels, despite her fast approaching wedding. Julia Roberts plays the lead role of Jules, whose best friend Michael (Dermot Mulroney) becomes engaged to the bubbly and sweet Kimmy (Cameron Diaz). Sabotage and hijinks naturally ensue, culminating in a bittersweet finish. The wedding of my best friend is strongly regarded as one of the greatest romantic comedies of all time and is a must-watch.

6 (500 days of summer

2009 romantic drama (500 days of summer stars Joseph Gordon-Levitt and Zooey Deschanel and centers on hopeless romantic Tom Hansen as he reflects on his failed relationship with the girl he believes to be his soul mate. He sets out to figure out what went wrong and win her back, analyzing the various events of their 500 days of courtship. Summer doesn’t believe in true love and Tom is a die-hard romantic, so naturally tensions run high and problems plague them. The refreshing romantic comedy (made at the height of the ‘manic pixie dream girl’ fandom) is quirky, charming and unique in its storytelling as it tells the audience how it will end at the very beginning with lead man Tom wondering why. .

5 Brokeback Mountain

Neo-Western romantic drama Brokeback Mountain depicts the complex and moving emotional and sexual relationship between two American cowboys over the course of 20 years. Heath Ledger stars as Ennis Del Mar and Jake Gyllenhaal as Jack Twist, a pair of shepherds who fall in love and endure a heartbreaking, raw and tragic romance. Their love story is beautifully brutal and depicts Ennis and Jack’s efforts to suppress their all-consuming passion and feelings. Brokeback Mountain was heralded as a turning point in the progression of queer cinema into mainstream audiences and features one of cinema’s most poignant and heartbreaking endings to date.

4 Forget Sarah Marshall

On the more comedic side of unrequited love, Jason Segel wrote and starred in the 2008 comedic farce Forget Sarah Marshall, which follows devastated songwriter Peter as he escapes on vacation to Hawaii after his TV star girlfriend, Sarah, breaks up with him. Kristen Bell stars as the titular Sarah, who leaves Peter for British rock star Aldous Snow (Russell Brand) and vacations at the same resort where her ex is.

Related: Movies That Made 2008 A Great Year For Comedy

Peter must come to terms with his grief and grief, while yearning for Sarah and their broken relationship. Mila Kunis stars as resort receptionist Rachel, who helps pull Peter out of his angsty depression and shows him that love can bloom again. The film is also fun not just about unrequited love, but how people eventually get over it.

3 To all the boys I’ve loved before

Netflix’s Teen Romantic Comedy To all the boys I’ve loved before is based on Jenny Han’s 2014 novel and centers on a teenage girl whose life is turned upside down when her secret love letters are exposed. Starring Lana Candor and Noah Centineo as Lara Jean and her crush Peter, the film follows Lara Jean as she deals with the fallout from her love letters sent to all her crushes and their various reactions. To all the boys I’ve loved before is one of the must-have mainstream romance movies to feature people of color in lead roles, and is a sweet and heartwarming romantic comedy that was a runaway hit for Netflix, and its success led to two follow-up sequels. .

2 Vacations

In Nancy Meyers’ star-studded romantic comedy Vacations, two discouraged women from opposite sides of the world decide to do a house swap over the Christmas season in hopes of escaping their respective messy love lives. Kate Winslet and Cameron Diaz appear as London-based society columnist Iris and Los Angeles trailer producer Amanda, who try to do some much-needed self-reflection after ending their problematic relationships. Iris is still madly in love with her ex despite the fact that he emotionally manipulates her and cheated on her on several occasions, so she leaves for sunny California after being taken aback by her engagement announcement. The feel-good film, which has become an inspirational Christmas staple in recent years, chronicles the growth both women experience as they discover their own worth and that fulfillment lies in themselves, not in a partner.

1 He’s just not very interested

Based on the self-help book by Greg Behrendt and Liz Tuccillo, the epic 2009 romantic comedy features an all-star cast including Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Ben Affleck and a plethora of more talented actors. The film focuses on nine people and their various romantic issues as they attempt to navigate the world of dating and romance. From unrequited affection to misinterpreted romantic interests, He’s just not very interested is an entertaining and illuminating film that sharply analyzes the treacherous realities of love and relationships.

The wide cast and character cast makes the romantic comedy shine from start to finish, and its title alone simply screams “unrequited love.” He’s just not very interested is a real crowd pleaser looking to entertain its audience – sometimes a movie loves you back, even when people don’t.

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