Plot
Max, an alpha-male, commitment-phobic sports broadcaster, and Jay, a neurotic novelist, have been best friends since childhood in Chicago. Jay has just broken up with his girlfriend, Natasha, and is writing his first book about their relationship in Milan, Italy. He is melancholic and has been drinking. Jay sets Max up with his editor, Samantha. After their first date, they each tell Jay in detail how terrible it was. Max claims Samantha was a loud, obnoxious drunk, while Samantha insists Max took her to a strip club. They then make out, burst out laughing, and admit they fooled him. Although they share few interests, they become engaged within two weeks, and shortly thereafter Max moves in with Samantha. While flipping through bridal magazines, Max is upset by a photo of Jay’s model ex, Natasha, and later drunk-calls her. When Max is confronted by a dream in which Sam is the last woman he will ever sleep with, he proposes a test: Jay will hit on Sam, and if she shows no interest, Max will feel confident enough in her loyalty to go through with the marriage. Jay does not want to do it. Nervous and conflicted, he initially suggests limiting his meetings with Sam, but soon finds himself seeing her several times a week. When the publisher moves up the book’s completion date to six weeks, Jay and Sam are forced to spend even more time together. Two weeks before the three plan to have a celebratory dinner for the book’s completion, Max has to travel to Detroit for work. Jay and Sam go out drinking and dancing, where Jay runs into Natasha. Sam pretends to be his new fiancée, and Natasha appears disheartened by the news. Later, Jay crashes at Sam’s apartment. After finishing the manuscript, she goes upstairs to talk to him. They share a near-kiss before her cousin, Dre, interrupts them. Jay leaves and goes to Natasha’s hotel room at her invitation. At the hotel, Natasha tears Jay’s clothes off, having rekindled her interest after seeing him with Sam. In the encounter, Jay realizes he is finally over her. He takes back the love memento he gave her and leaves. Feeling guilty about his sudden recognition of his feelings for Sam, he calls Max and discovers that Max has slept with his makeup artist, Dara. Jay rushes to Sam’s apartment but loses his nerve and goes home instead, drinking heavily. Max finds him there and confronts him about Sam. After a heated altercation, they agree to go to Sam and let her decide what she truly wants. Over a meal, Jay declares his love for Sam and kisses her. Max is shocked but then begins to laugh, assuming it is a joke, and reveals the fidelity test he had asked Jay to perform. Upset, Sam leaves, cutting ties with both men. Max and Samantha refuse to talk to each other. Jay moves to New York City. Max finally reads the book he had previously recommended and realizes he needs to reunite Jay and Sam. When Jay returns to Chicago for his book signing, Max leaves him a note asking him to meet at a restaurant and enlists Dre to bring Sam there as well. Once they are seated separately, Max has notes delivered to both of them. At their wedding, Max gives them his blessing, remarking, “Love cannot be found where it does not exist, nor can it be hidden where it truly does.” Jay and Sam dance together, while Max dances with Linda, implying the beginning of a relationship between them. ==Cast==