When beloved Springfielder "Chip Davis" dies, four residents recall life events that they would like to do over. Among them: Homer bemoans selling a tech stock to purchase a bowling ball, and Marge fears that she's the reason Bart is such a rebellious child.
Others wishing for a do-over are Mr. Burns, who recalls a long-ago romance with a lovely Parisienne, and newsman Kent Brockman who regrets not leaving the local station to take a job with cable news.
At the First Church of Springfield, everyone is at the funeral of Chip Davis. Some Springfielders recalled how Chip helped them with their problems. When it was revealed that Chip had a few regrets, Patty states everyone has regrets.
When Marge states she has no regrets, Patty tells her that her marriage with Homer is poor, Maggie is addicted to pacifiers, and that Bart is out of control.
After Bart pranks everyone at church, Marge recalls her pregnancy with Bart being perfect and then realizes that Bart may have been effected by the KISS music she was listening too. Kent Brockman is also having regrets about his career as a news reporter.
Then Homer recalls the worst financial decision he's ever made. In early 2001, Homer is at Alley McBalls, looking at bowling balls. He then makes a call to Bearsterns to sell all of his apple stock to buy a blue colored bowling ball.
After the flashback ends, everyone in the church soon starts texting on their apple tablets and phones. Homer then accuses the bowling ball of costing him all of the stock, causing the ball to cry.
Mr. Burns reveals he bought the stock Homer sold and Homer replies that Mr. Burns has no regrets at all. Mr. Burns reveals that he does have one, a girl that got away and broke his first heart.
After the funeral ends, Bart and Milhouse steal Timothy Lovejoy's robes to prank everyone again. Both Bart and Milhouse soon fight each other with the collection baskets.
The flashback shows Marge wanting to listen to the KISS record and Homer throws a number of books into the fire, which basically teaches the parent how to raise kids and set up college funds. The fight between Bart and Milhouse ends when Milhouse is on top of a car that is being driven away.
At the end of the episode, before the credits, a tribute to Marcia Wallace is shown, with Mrs. Krabappel in her classroom. She then says her catchphrase "Ha!"