When Homer gets his arms stuck in two vending machines and cannot attend the ballet with Marge, she invites her neighbor, divorced Ruth Powers, to take his place. The two women have a great time and agree to go out again.. The following evening, Ruth pulls up in a 1966 T-Bird convertible wearing jeans and a leather jacket.

Homer wants his own night out and hires attourney Lionel Hutz to babysit. Meanwhile, Ruth and Marge hit several trendy nightspots before driving to the Springfield sign that overlooks the town. Homer arrives just as they are leaving, and runs into Chief Wiggum, who offers to drive him home. Homer hitches a ride with Chief Wiggum. When Wiggum tries to pull over Ruth's car for a minor infraction, Ruth speeds off, admitting to Marge that she stole the car from her ex-husband.

With Homer inthe back seat, Wiggum gives chase. Soon he is joined by several other police cars. Ruth wants to give herself up, but Marge, loyal to her friend, turns the steering wheel towards the desert to help her escape. As their car approaches a chasm, Homer takes a bullhorn and apologizes to Marge for being a poor husband. Marge and Ruth stop the car just in time, but Wiggum and Homer, following closely behind, sail over the cliff, landing safely on a massive pile of garbage.