The best movies about unrequited love for Valentine’s Day

Unrequited love (dating all the way back to ancient greek tragedy) is a highly exploited trope in Hollywood and has been portrayed in numerous films over time, with varying degrees of longevity and success. A one-sided love story have the power to move and touch audiences, as their plight can often enchant, frustrate and entertain the masses. This style of storytelling is no stranger to the silver screen, with some of the most memorable and iconic films this adopts heartbreaking concept to greater effect as others.

Whether it be the all-consuming love of a literary great, the deceived attempts of a hopeless romantic, or the desperate longing for an unattainable crush, stories of unrequited love have always found a permanent home in Tinsel Town. True love may not be like movie love, but with Valentine’s Day right around the corner and many people experiencing the highs and lows of romance, let’s watch some of the best movies about unrequited love.

10 Beautiful in pink

10 beautiful in pink facts you never knew
Paramount Pictures

The iconic 1986 teen rom-com Beautiful in pink tells the story of a love triangle between a girl who has to decide between her feelings for her childhood best friend and a rich yet sensitive player. 80’s sweethearts Molly Ringwald, Jon Cryer, and Andrew McCarthy play the love trio in the acclaimed “Brat Pack” movie, written by the beloved John Hughes and directed by Someone Wonderfulsee Howard Deutsch. Related and down-to-earth Andie (Ringwald) loves the preppy rich child Blane, and is completely unaware that her best friend and fellow outsider Duckie has been looking after her for years. The original ending actually let underdog Duckie get the girl, but test audiences cheered that end and Hughes rewrote it so that Andie and Blane could get together sooner. Sorry, Duckie.

9 Ghost World

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United Artists

Terry Zwigoff’s critically acclaimed black comedy Ghost World centers on the lives of Enid and Rebecca, two teenage outsiders whose once solid friendship becomes strained when Enid becomes interested in an older man’s love life. With the talented Thora Birch and Scarlett Johansson as the duo and Steve Buscemi as a lone middle-aged record collector, Ghost World is based on the Daniel Clowes cartoon of the same name. Enid makes it her mission to help the withdrawn Seymour find a wife, but in the process develops a love affair with the older man. While not exactly a typical Valentine’s Day staple, Ghost World take audiences on a journey of self-exploration and portray adolescent pains flawlessly.

8 Love Actually

Love Actually
Universal pictures

One of the most iconic film depictions of unrequited love, 2003s Love Actually follows the lives of eight heavenly different couples a month before Christmas while their stories are accidentally woven together. Mark (Andrew Lincoln) is hopelessly in love with his best friend’s new bride Juliet (Kiera Knightley) and in his attempts to hide his feelings he comes across her carelessly and seemingly cold. When Juliet tries to smooth their relationship, Mark is inspired to declare his love for her through a tree box and big cue cards. Love Actually has become a contemporary Christmas classic and captures the heartbreaking realities of unrequited love perfectly.

Related: Best Christmas Movies of the 2000s

7 The Great Gatsby

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Warner Bros. Pictures

Baz Luhrmann’s astonishing processing of the beloved F. Scott Fitzgerald novel The Great Gatsby tells the story of millionaire Jay Gatsby as he meets his neighbor Nick Carraway and searches the Roaring Twenties for his ex-girlfriend Daisy Buchanan. Leonardo DiCaprio and Carey Mulligan portray the fatal lovers, while Tobey Maguire plays the aspiring writer Nick. The heartbreaking love affair between Jay and Daisy is notorious and ends up in tragedy, but to see it unfold is a deeply moving experience for audiences. Luhrmann’s typically brilliant approach The Great Gatsby is an unforgettable and raw depiction of the highs and lows of love.

6 My best friend’s wedding

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Sony Pictures Released

Probably one of the most popular unanswered 90s love movies, 1997 se rom-com My best friend’s wedding follows a woman who realizes she is in love with her best friend after announcing his engagement. She then embarks on a mission to win him over and tell him how she feels, despite his fast-approaching marriage. Julia Roberts plays the lead role as Jules, whose best friend Michael (Dermot Mulroney) becomes engaged to the bubbly and sweet Kimmy (Cameron Diaz). Sabotage and hijackings occur naturally, resulting in a bittersweet finale. My best friend’s wedding is highly regarded as one of the greatest romantic comedies of all time and is a staple for Valentine’s Day.

5 (500 days of summer

Joseph Gordon-Levitt agrees: Tom was the real villain in (500) days of summer
Fox Searchlight Pictures

2009’s romantic drama (500 days of summer starring Joseph Gordon-Levitt and Zooey Deschanel and focuses on the hopeless romantic Tom Hansen as he reflects on his failed relationship with the girl he believes is his soulmate. He begins to find out what went wrong and to win her back, analyzing the various events of their 500-day courtship. Summer does not believe in true love and Tom is an ordinary romantic, so the tension naturally runs high and problems hit them. The refreshing rom-com (made at the height of ‘manic pixie dream girl’ fandom) is unbeatable, charming and unique in its storytelling, as it tells audiences how it will end at the very beginning with starring Tom wondering why.

4 Brokeback Berg

Jake Gyllenhaal is held by Heath Ledger in Brokeback Mountain.
Focus features

Neo-Western romantic drama Brokeback Berg depicts the complex and moving emotional and sexual relationship between two American cowboys over the course of 20 years. Heath Ledger plays Ennis Del Mar and Jake Gyllenhaal as Jack Twist, a couple of shepherds who fall in love and endure a heartbreaking mourning and tragic romance. Their love story is beautifully brutal and depicts the efforts Ennis and Jack make to suppress their passion and all-consuming feelings. Brokeback Berg was announced as a turning point for the progression of queer film to the mainstream, and contains one of the most moving and heartbreaking endings in film to date.

3 Forget Sarah Marshall

Universal pictures

Jason Segel wrote and starred in the 2008 comedy joke Forget Sarah Marshall, what follows destroyed composer Peter as he escapes on a Hawaiian vacation after his TV star girlfriend Sarah breaks up with him. Kristen Bell plays the titular Sarah, who leaves Peter for British rock star Aldous Snow (Russell Brand) and happens to be on holiday at the same resort that is her ex. Peter must make peace with his grief and sorrow, while still longing for Sarah and their broken relationship. Mila Kunis plays as the receptionist Rachel, who helps to get Peter out of his anxiety-stricken collapse and shows him that love can flourish again. The film looks just as funny at unrequited love, but at how people finally get over it.

Related: Why Charlie Hunnam said no to forgetting Sarah Marshall’s role for him

2 To all the boys I used to love

To all the boys: PS I still love your photo # 1

Netflix teen rom-com To all the boys I used to love is based on the 2014 Jenny Han novel and is about a teenage girl whose life is turned upside down when her secret love letters are revealed. With Lana Candor and Noah Centineo as Lara Jean and her beloved Peter, the film follows Lara Jean as she deals with the outbursts of her love letters sent to all her loved ones and their diverse reactions. To all the boys I used to love is one of the much needed mainstream romance movies to show people of color in leading roles, and is a sweet and moving rom-com that was a runaway hit for Netflix, and its success led to two follow-up stories.

1 He’s just not like that in you

He's just not like that in you
Warner Bros. Pictures

Based on the Greg Behrendt and Liz Tuccillo self-help book, 2009’s epic rom-com features an all-star ensemble 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 problems as they try to navigate the world of dating and romance. From unrequited love to misreading romantic interests, He’s just not like that in you is an entertaining and enlightening film that sharply analyzes the insidious realities of love and relationships. The wide range of cast and characters make the rom-com shine from start to finish, and the film is a true crowd-pleaser that seeks to entertain its audience; sometimes a movie loves you, even when people do not.

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