Jon is a young man who objectifies everything in his life from cars to women. After he realizes that watching adult entertainment gave him unreal expectations about life and relationships, he decided to go out and tries to find a more meaningful companionship.
What he gets is lessons in life and relationships from two very different women.
I think Joseph Gordon-Levitt did a pretty decent job at playing the writer/director/actor role. You think the movie is going in one direction, and then it makes a sharp turn, but ultimately leads to the reward. The movie has got it's flaws -- it sometimes seems like a vanity piece for him -- but overall, I thought it was a pretty solid film..