Romantic comedy: Will Hayes, a 30-something Manhattan dad is in the midst of a divorce when his 10 year old daughter, Maya, starts to question him about his life before marriage. Maya wants to know absolutely everything about how her parents met and fell in love. Will's story begins in 1992, as a young, starry-eyed aspiring politician who moves to New York from Wisconsin in order to work on the Clinton campaign. For Maya, Will relives his past as a idealistic young man learning the ins and outs of big city politics, and recounts the history of his romantic relationships with three very different women. On the campaign, Will's best buddy is Russell McCormack. They not only have similar political aspirations, they share the same type of girl problems, too. Will hopelessly attempts a "PG" version of his story for his daughter ad changes the names so Maya has to guess who he finally married. Is her mother Will's college sweetheart, the dependable girl next-door Emily? Is she his longtime best friend and confidante, the apolitical April? Or is she the free-spirited but ambitious journalist? As Maya puts together the pieces of her dad's romantic puzzle, she begins to understand that love is not so simple or easy. And as Will tells her his tale, Maya helps him to understand that it's definitely never too late to go back...and maybe even possible to find a happy ending.

The needy Gigi Haim is a young woman seeking her prince charming somewhere amongst her unsuccessful dates. After dating estate agent Conor Barry, Gigi anxiously expects to receive a phone call from him. However Conor never calls her. Gigi decides to go to the bar where he frequents to see him, but she meets his friend Alex who works there. They become friends and Alex helps Gigi to interpret the subtle signs given out by her dates.

Kassie (Jennifer Aniston) and Wally (Jason Bateman) are best friends. Being unlucky in love, Kassie has decided to have a child using artificial insemination. Wally doesn't like this idea, but he isn't capable of admitting to himself, let alone to Kassie, that he's in love with her. At Kassie's artificial insemination party, Wally gets very drunk and spies the sperm donor's sample in the bathroom. Wally was way too drunk to know what he did that night, and Kassie has moved away because she doesn't feel that New York City is a place to raise a child. Now 7 years later, Kassie has moved back with her son Sebastian. While she is looking to get Roland (the sperm donor) more involved in their lives, Wally can't help but notice the many striking similarities that he and Sebastian share.

The movie is based on the young adult book, The Sisterhood of the Traveling Pants, by Anne Brashares. As four best friends spend their first summer apart from one another, they share a magical pair of jeans. Despite being of various shapes and sizes, each one of them fits perfectly into the pants. To keep in touch they pass these pants to each other as well as the adventures they are going through while apart.

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