Jon Martello, portrayed by Joseph Gordon-Levitt, embodies the archetype of a modern-day Don Juan, living a life defined by a narrow set of priorities: "my body, my pad, my ride, my family, my church, my boys, my girls, my porn." His life of casual encounters and nights out with friends involves frequenting nightclubs and immersing himself in the world of online pornography—a habit that provides him escapism but ultimately leaves him unfulfilled.
One fateful evening, while out with his close pals, Jon encounters Barbara Sugarman. Despite an initial connection, he fails to charm her into a one-night stand. Undeterred, Jon takes to Facebook to learn more about her and invites her to lunch. Their chemistry is undeniable, yet Barbara insists on a more traditional courtship that unfolds over the course of a month, devoid of physical intimacy. Encouraging Jon to pursue night classes for an office job—something he has yet to consider—she introduces him to the world of romance films, which he initially scoffs at for their "unrealistic fantasy." As their relationship deepens, they both meet each other's families, and Jon's parents quickly warm up to Barbara.
Their romance reaches a physical culmination, but Jon's dissatisfaction remains. Soon after their first intimacy, he sneaks away while Barbara sleeps to indulge in his usual pornography habit. When Barbara discovers this betrayal, she is left reeling, confronting Jon about his compulsive activities, which he initially brushes off as a joke.
Despite their efforts to work through these challenges, Jon resumes watching pornography frequently, often in places where Barbara may not see him. An encounter with Esther, a middle-aged woman at his class, adds another layer to Jon's struggles. Though Esther tries to guide him away from his troubled relationship with pornography, it leads to a complicated connection between the two, culminating in an unexpected sexual encounter in her car.
As their relationship evolves, Esther shares her tragic backstory of losing her husband and son, emphasizing the importance of mutual connection in intimate relationships. This advice finally guides Jon toward experiencing sex in a way that fills him with a sense of completeness rather than prompting him toward further escapism. He transitions from a notebook filled with confessions of casual encounters to one highlighting his resolve to abstain from pornography and the newfound depth of intimacy he discovers with Esther.
When Jon eventually reveals the breakup with Barbara to his family, their devastation is palpable, yet his sister candidly points out that Barbara's feelings were superficial, merely an extension of her fantasy. In a moment of clarity, Jon reaches out to Barbara to apologize for his earlier dishonesty regarding his pornography habits, but her inability to acknowledge his perspective solidifies his realization that he is better off without her.
In a transformative moment at the gym, Jon shifts his focus from weightlifting to connecting with friends over basketball, and he embraces a relationship with Esther. Although neither exhibits a desire for marriage or declares love, they find joy in losing themselves in one another, culminating in a new beginning that reflects deeper intimacy and understanding than his former life ever provided.
