Joe recounts the tale of the first date he's gone on in 20 years. The misadventures include a black eye, a potentially embarrassing encounter with one of his employees, an unfortunate piece of advice from Terry, an anxious Little Leaguer and a poorly placed lamp.

Joe's bookie finds out Joe used to be a professional golfer and decides to use him to hustle a couple of guys. Owen's family becomes concerned over his increasing weight. And Terry gets a new apartment, but the apartment manager job that comes with it is a bit much to handle.