A young man abandons his family for a solitary life of fly-fishing. His goal was to find his own way in the fishing world and thereby find himself and love.

Frustrated with their relationship, Priscilla and Jack decide to take a break. While Jack moves into a new place of his own and starts dating a student, Priscilla discovers the joys of self-pleasuring and finds an unusual bedmate.

Ben Singer (Matthew Broderick) is a failed children's folk singer, a career proofreader, a compulsive marijuana smoker, and a less-than-extraordinary weekend dad. He's also the most negative man alive. Floundering in all aspects of his life, Ben's only comfort comes from regular chess games and friendly debates on game theory with his Senegalese roommate Ibou. When Ibou is suddenly struck ill, and an insensitive municipal employee exacerbates the emergency situation, Ben's pessimistic worldview seems unequivocally confirmed. His only recourse is to pour his energies into a frivolous lawsuit against the city for depraved indifference. But Ben soon finds that cynicism may be all a matter of perspective.