After their marriages fail, Oscar and his former college roommate, Felix, decide to live together.

Felix’s hypochondria kicks into overdrive when Oscar starts dating the most important person in Felix’s life – his doctor.

Felix convinces Oscar to appear on a sports television show against Teddy’s advice to stick with radio.

When Oscar and Felix make a trip to Ashley's to retrieve Felix's special pillow, a secret that he has kept from Oscar is revealed.

Oscar becomes weirdly obsessed with living up to Murph’s reputation when he finds out that the girl he is seeing used to date the handsome ex-baseball player.