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, an 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, 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 to pretend to be an interested homebuyer at an open house.
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 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 goes to see his retired father, who gives new meaning to the word grumpy. Owen's wife and mother get upset when a commercial for the auto dealership implies that Owen's co-worker, Marcus, is actually Owen Sr.'s son. And Terry becomes obsessed over finding out why he has been rejected for a youth mentoring program.
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.
Joe is desperate to buy a house after his son's anxiety issues worsen. Terry must face the dire condition of his acting career when he meets a successful buddy from his past. At the dealership, Owen and the sales team confront a particularly tough customer.
Feeling guilty about his rapid downward spiral, which includes out of control gambling and having to cut back on staff at his store, Joe decides to stop gambling. Owen finds a new sense of purpose when he goes to work for a rival auto dealership following his father's decision to turn management over to Marcus. And Terry's life spins out of control when his gig on a movie results in disasters at the apartment complex he manages.