Gordon-Levitt stars as New Jersey playboy Jon Martello in this romantic comedy, which he also writes and directs. His character is addicted to pornography even though he is popular among women and does not have any problems having flings on a regular basis. He dates Barbara Sugarman, played by Scarlett Johansson, and both of them struggle to stay together due to their varying ideas of love and relationships. The film also stars Tony Danza, Glenne Headly, and Julianne Moore. On his first stint as director:
I really wanted this movie to have a flair to the filmmaking. Especially comedies, it seems, often stay pretty conservative and just leave the comedy to the writing and acting and the rest of the filmmaking is very standardized. I didn’t want to do that. I wanted the filmmaking to reflect what was going on with the character and the evolution of the character.