In 1993, Coles (Mark Ruffalo) meets Sam (Maya Stange) at a party after seeing her a few hours earlier on the subway. Their attraction is mutual, and when he suggests they go to her room, she wants Thea (Kathleen Robertson) to join them in a menage a trois. The two women seem relaxed with the stranger and he is enjoying the experience until Sam shatters the magic and the mood by leaving the bedroom in tears. Later she decides to begin a love relationship with Coles. But she is somewhat perplexed by his need to joke around about everything. He usually responds to questions with another question. Coles, who dreams of making movies some day, has told her that he doesn't want to grow up. He definitely is a Peter Pan male who loves his wild and irresponsible life.

One evening when Sam goes out dancing, he has sex with another woman. For him it doesn't mean anything but when Sam hears him say the words, she doesn't believe him. Coles crosses the forbidden barrier when he has sex with Thea another night. Sam walks out on him.

Ten years later, the two of them bump into each other on the street in New York. Coles has made an unsuccessful film and settled down in a prosperous career as an animator for an ad agency. He has been living with Claire (Petra Wright) for five years but hasn't married her. Sam has just returned from London, having broken off her engagement to a young man. She reports that Thea is happily married to Miles (David Thornton) and runs a restaurant with him. Of course, Coles and Sam both wonder what would have happened if they would have stayed together. In an incisive scene in the bathroom while brushing their teeth and flossing, Coles and Claire talk about Sam, a young actor she is dating, Thea, and Miles. She has correctly intuited that he still has strong feelings for his old flame. On a week-end in the Hamptons, Coles is forced by circumstances beyond his control to declare his true colors.

Writer and director Austin Chick has a fondness for French filmmakers and in one crucial scene, Claire arrives home with a gift of tapes by Claire Denis. The one scene in the drama where Coles is humbled and responds with kindness is an awkward situation when a young man recognizes him as a filmmaker and asks for his money back since he was disappointed with the movie. The fellow claims that his girlfriend didn't like it much either, in fact she was turned off by its treatment of women. Coles graciously gives him his money back.

He is not as sensitive in his treatment of Claire who has tried for years to move him toward taking responsibility for the choices he makes. XX/XY is very telling with its raw portrait of male indecisiveness and immaturity in matters of the heart.