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Benjamin Barry (Matthew McConaughey) is an advertising executive and a ladies' man who makes a bet, in order a big campaign, with his coworkers that he can make a woman fall in love with him in 10 days. He meets Andie Anderson (Kate Hudson) who ironically is writing an article for the magazine she works for about "how to lose a guy in 10 days". At the end, both of them reveal their true motives, however, their initial desires have changed.
Will Hayes (Ryan Reynolds) is asked by his 11-year old daughter Maya (Abigail Breslin) to tell the story of how he met her mother. He decides to make it a puzzle for her and changes the names of all the girls so she must figure out which one of the 3 loves of his life is her mother. Maya begins to understand that love is not so simple and eventually solves the puzzle.
Peter (Jason Segel) decides to take a trip to Hawaii in order to overcome his recent break up with his TV star girlfriend, Sarah (Kristen Bell). Little does he know, Sarah is vacationing at the same hotel as him with her new beau. A thoughtful hotel clerk, Rachel (Mila Kunis), feels bad for him and invites him to hang out. Although he constantly runs into Sarah and her boyfriend, Peter begins to come alive again and Sarah realizes what a mistake she has made.