Meet Reuben Feffer (Ben Stiller). He is a bit uptight and all buttoned up guy who likes having his life all listed and organized. After he had married the most beautiful girl in the world and was happy, two of them went off on a honey moon. There, he caught her cheating on him with a scuba diving guy. So, there is only thing he could do- pack his things and go back home. As he files for divorce and starts getting his life back in the normal, his best friend Sandy Lyle (Philip Seymour Hoffman) talks him into going out. And that is the night when an old spark got lit up again when he saw his old high school friend Polly Prince (Jennifer Aniston). From that point on, he starts trying to contact her, charm her, get her to like him. And while doing that, he encounters more problems than he thought he would. From getting into most embarrassing situations ever, like getting the toilet plunged in her house, to dancing salsa all sweaty with other people, which he hates the most, Reuben finds himself doing everything he never thought he would, just because he is in love with her. And one of his sentences, that shows how much he cares, is precious: "Since we have been together I have felt more uncomfortable, out of place, embarrassed, and just physically sick then I have in my entire life. But I could not have gone through that, I could not have thrown up 19 times in 48 days if I was not in love with you."