Jason, our hero, is his own worst enemy when it comes to women and dating. Awkward and neurotic, he's been on 22 internet dates and counting when he meets Chloe, a girl with relationship issues of her own, who, much to his surprise, decides to take him home with her. Then in the morning, she hands him a cup of coffee in a travel mug and tells him to come back that night at 11pm. Rather than be overjoyed with his newfound good fortune, Jason over thinks everything. Their dueling self-esteem issues make communication difficult, and the more Chloe just wants to have sex, the more Jason manipulatively tries to create the trappings of a relationship, until in the end, he learns to be careful what he wishes for.