Joe, Owen and Terry have been friends for years. Joe, a party-store owner who once had dreams of being a professional golfer, struggles with his recent separation from his wife. Owen, a put-upon auto salesman, tries to make ends meet while working for his demanding father. And Terry, a handsome part-time actor, hopes to recapture the glory of his past. Between daily lunches at a local diner and hikes in the hills overlooking Los Angeles, the three do their best to support each other through the challenges mid-life throws at them.

Joe has been living in a hotel since separating from his wife, Sonia (guest star Penelope Ann Miller), but he's starting to think about finding an apartment. Owen, who is one of the auto dealership's weakest salesmen, winds up with an embarrassing dealer car, one his wife simply will not accept. And Terry goes overboard trying to track down a man who nearly ran him over.

Joe tries to connect better with his son, Albert, by teaching him golf. But when the school golf team is ready to compete in a tournament, Albert is reluctant to get on the bus. Owen is determined to get his sales figures up while at the same time not feeling bad about himself for ripping customers off. And Terry gets into his character a little too much when a coworker asks him and an actress (guest star Cynthia Watros) to pretend to be an interested homebuyer at an open house.

Owen and Melissa join Joe's ex-wife, Sonia, and her new boyfriend, Harold, for a charity function at their children's school. Terry does his annual duty as auctioneer for the event and meets an old flame, while Joe winds up hanging out with his bookie, Manfro.

The construction at Owen's house is shut down by the city when it is discovered that the contractor, who has now disappeared, never filed the proper permits. To make matters worse, the electricity is out, forcing Owen and his family to temporarily stay with his parents. Meanwhile, Joe worries that his daughter's ex-boyfriend might be stalking her.

Joe recounts the tale of the first date he's gone on in 20 years. The wild 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.