Jon Martello Jr. (played by Joseph Gordon-Levitt) is a young man from New Jersey who is obsessed with pornography and one-night stands. He enjoys watching porn and masturbating more than having actual intimacy with women. Despite his successful career and strong relationships with his family and friends, Jon finds himself feeling unfulfilled and empty.
One day, Jon meets Barbara Sugarman (played by Scarlett Johansson) at a club and becomes infatuated with her. Barbara is a confident and attractive woman who has high expectations for her partner. Jon starts dating Barbara, but soon realizes that she shares his obsession with romantic comedies and has her own unrealistic expectations about relationships.
As their relationship progresses, Jon struggles to balance his addiction to pornography with his desire for a real connection with Barbara. He also starts attending night classes at a community college, where he meets Esther (played by Julianne Moore), who helps him understand the difference between sex and intimacy.
Through his interactions with Esther and his growing self-awareness, Jon begins to question his beliefs about love and relationships. He learns that true happiness and intimacy come from genuine communication and emotional connection, rather than superficial fantasies.
In the end, Jon must confront his own insecurities and issues in order to find true fulfillment and happiness with a potential true love. The film explores themes of love, addiction, and self-discovery, and ultimately delivers a powerful message about the importance of genuine human connection.