Theodore is a lonely man in the final stages of his divorce. When he's not working as a letter writer, his down time is spent playing video games and occasionally hanging out with friends. He decides to purchase the new OS1, which is advertised as the world's first artificially intelligent operating system, "It's not just an operating system, it's a consciousness," the ad states. Theodore quickly finds himself drawn in with Samantha, the voice behind his OS1. As they start spending time together they grow closer and closer and eventually find themselves in love. Having fallen in love with his OS, Theodore finds himself dealing with feelings of both great joy and doubt. As an OS, Samantha has powerful intelligence that she uses to help Theodore in ways others hadn't, but how does she help him deal with his inner conflict of being in love with an OS?

Erin has just six more weeks as an intern at the New York Sentinel before she returns to San Francisco. That's fine with Garrett since he just got out of a relationship. But their relationship blossoms and it quickly becomes something that they can't just drop in six weeks. They admit to wanting to be boyfriend/girlfriend just on opposite coasts. The distance wears on them, as with their nay-saying friends and sister, and soon they are forced to either break up or come up with a solution that has them living in the same city.

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.

Danny (Adam Sandler) must engage Katherine (Jennifer Aniston), his faithful assistant, to pretend to be his soon to be ex-wife. Danny must pretend that he is married, because he lied to his dream girl, Palmer (Brooklyn Decker) the most gorgeous woman in the world. To keep the woman he loves, covering up one lie soon turns into many lies.

Pivoting around the eternal game of love, the suave matchmaker and New York City's finest date-doctor, Alex "Hitch" Hitchens, can guarantee that any man can get the girl of his dreams if he overcomes his fears and follows his infallible advice. However, when the timid accountant, Albert Brennaman, enlists his help to catch the attention of the rich and beautiful heiress, Allegra Cole, Hitch will unexpectedly discover his perfect match: the inquisitive gossip columnist, Sara Melas. Now, the self-assured charmer finds himself in need of his services to save his relationship. But, can the silver-tongued expert of romance survive the delicate complications of love?

Rachel is a lawyer. When she was in law school she fell for another student, Dex, who comes from an affluent family, but she was too shy to say anything. When Dex meets her best friend Darcy, who sometimes treats her like dirt, Darcy makes a move on Dex and gets him. Eventually, they get engaged and Darcy asks Rachel to be her Maid of Honor. However, Rachel still has feelings for Dex and still can't say anything. Darcy throws her a birthday party and Dex is there. When she and Dex are alone she blurts out that she had a thing for him in college which surprised him, and after drinking a little they spend the night together. They try to forget the whole thing and agree that it means nothing. Ethan, Rachel's close friend, tells her that she'll spend her entire life regretting that if she does nothing.

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