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Fun fact: was directed by Forest Whitaker, who also directed Whitney in the “Exhale (Shoop Shoop)” music video.What happens when you pair a recently retired hockey player with a figure skating star who’s spoiled AF?Julia Roberts and Dermot Mulroney play best friends who made a pact to marry each other if they didn't find the love by 28 (lol, yes, 28).With her birthday fast approaching, he announces an unexpected engagement — and she realizes she's in love with him and must sabotage the wedding.At first Alison (Katherine Heigl) and Ben (Seth Rogen) don’t seem to work, but by the end of the movie, you’ll be sold.In this underrated gem, Oliver (Ashton Kutcher) and Emily (Amanda Peet) go from friends with occasional benefits to just friends to lovers over the course of several years.These kinds of relationships rarely work out in real life, which is one reason they’re so fun to watch on screen.Most people don’t carry flames for their high-school classmates for ten years, but most people don’t look like Ryan Reynolds and Amy Smart.

After meeting on a train in Europe, Jesse and Celine spend all night walking and talking in Vienna.In this one, she plays a copy-editor who goes back to high-school undercover for a big-break story — and falls in love with a teacher in the process.The movie makes the list for many reasons: the wardrobe, the Shakespeare references, the existence of Molly Shonnon.It's brought to you by the Farrelly Brothers, the guys who did directed by her).The story follows a widower named Sam (Tom Hanks) who calls into a radio show to discuss his heartbreak and attracts the attention of countless female listeners.

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