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Underrated & Thought-Provoking Romance Films

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This stack goes beyond the typical Hollywood endings and explores romance in its various forms including films that are unconventional, bittersweet, or that challenge traditional notions of love.
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Once (2006)

A modern-day musical about a busker and an immigrant and their eventful week in Dublin, as they write, rehearse and record songs that tell their love story.

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The Way We Were (1973)

During post-WWII McCarthyism, a diametrically opposed couple come together only to find out that genuine friendship and physical attraction is not enough to overcome fundamental societal beliefs.

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My Best Friend's Wedding (1997)

When a woman's long-time friend reveals he's engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding.

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Ditto (2000)

Two students, separated in time, are somehow able to talk to each other using amateur radio, one in 1979 and the other in 2000.

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Forces of Nature (1999)

A soon-to-be-married man encounters an exciting stranger after his plane suffers an accident on takeoff.

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500 Days of Summer (2009)

After being dumped by the girl he believes to be his soulmate, hopeless romantic Tom Hansen reflects on their relationship to try and figure out where things went wrong and how he can win her back.

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Shakespeare in Love (1998)

The world's greatest-ever playwright, William Shakespeare, is young, out of ideas, and short of cash, but meets his ideal woman and is inspired to write one of his most famous plays.