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The Sweetest Thing

For a fun, playful film, watch Cameron Diaz, Christina Applegate, and Selma Blair in 2002's The Sweetest Thing. In it, Cameron's character finds love, loses it, and sets out to find it — as in, him — again.

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Gwyneth Paltrow stars in 1996's Emma, based on the classic Jane Austen novel — which is also the inspiration behind Clueless. Ever the matchmaker, Emma tends to meddle in everyone else's love lives without considering her own. When she does, she realizes that her one true love has been right there all along.

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In 2009's TiMER, people have biotechnological implants that count down to the moment they'll meet their soul mate. The comedy follows the story of Oona, a 30-something woman who's worried because her timer isn't ticking.

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Sleepless in Seattle

Before Internet dating and You've Got Mail, there were radio shows! Sleepless in Seattle (1993) is an Oscar-nominated classic that follows a young boy who sets his dad up with a woman after hearing her speak on the radio.

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The Spanish film Sidewalls takes a look at love in the era of the Internet. Mariana and Martin are the perfect couple, and they live right next to each other, but they've never met.

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His Girl Friday

You may reconsider an office romance when you watch His Girl Friday, which is about a newspaper editor who's trying to prevent his ex-wife — and also his star reporter — from remarrying.

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Silver Linings Playbook

Jennifer Lawrence and Bradley Cooper star in Silver Linings Playbook, a 2012 romantic comedy about two pretty . . . troubled characters who end up falling for each other.

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Thanks For Sharing

In the indie romantic comedy Thanks For Sharing (2012), Mark Ruffalo stars as a recovering nymphomaniac who ends up getting involved with Gwyneth Paltrow's character.

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Drinking Buddies

Work and love collide in the indie rom-com Drinking Buddies, which stars Olivia Wilde, Jake Johnson, Anna Kendrick, and Ron Livingston.

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A loose adaptation of Jane Austen's novel Emma, Clueless has become a 1995 cult-classic romantic comedy about the struggles of high school and unlikely love.

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Don Jon

Joseph Gordon-Levitt and Scarlett Johansson star in Don Jon, a film about a porn-addicted New Jersey guy trying to find love despite everything that's holding him back (like his bashful and opinionated family).

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Breakfast at Tiffany's

Breakfast at Tiffany's, one of Audrey Hepburn's most iconic films, is about her character Holly Golightly — a spritely and vivacious woman looking for love and luxury in the big city.

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Eagle vs. Shark

Eagle vs. Shark is the quirky tale of two awkward New Zealanders who fall in love.

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Ira & Abby

Ira & Abby (2006), starring Chris Messina of The Mindy Project, is an unconventional comedy about the complications of love.

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She's All That

It's the classic tale of boy meets girl, boy bets his friend he can turn girl into prom queen, girl gets a makeover by taking off her glasses in 1999's She's All That.

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The Princess Diaries 2: Royal Engagement

In The Princess Diaries 2: Royal Engagement, Mia Thermopolis, princess of Genovia (played by Anne Hathaway), is told she must be married before being able to take on the role of queen. As she struggles to find true love as swiftly as she can, a jealous Chris Pine gets in the way.

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Next Slideshow Smart Dating Advice From Our Single-Lady Hero Mindy Kaling BY Tara Block
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