New policies eliminate hugs and napping in the workplace. John's son gets thrown out of Yale after feigning insanity, but lands on his feet by becoming John's new boss. John quits his job in protest and says that he will concentrate on his writing. Eggers dates a Christ-like figure.

A young woman informs John that he's one of three men who could be her biological father.

Carly's 21-year-old brother has eyes for Catherine, but his age -- and John -- aren't the only obstacles to winning her heart: despite his fabulous income from bike racing, he is illiterate.

Old flames resurface after John and Catherine agree to take a break to assess the direction of their relationship.

John finally proposes to Catherine, she accepts, and everyone shows up for the wedding -- except the bride and groom. John accepts Carly's eager proposition to come home with her for the evening. But he disappoints Carly by proclaiming that he still loves Catherine. Mahalia advises John to call a psychiatrist, but after John reveals his deepest feelings--and his identity--he's mortified to realize that he's talking to radio psychiatrist, Dr. Frasier Crane live on the air. Determined to win Catherine back, John asks Catherine to marry him. Meanwhile, the St. Louis, Missouri Crossroads Bus Terminal begins closing at midnight.