The Simpsons (1989): Season 25, Episode 3

25 - 3: Four Regrettings and a Funeral

Four Springfielders are prompted to try to right past regrets following the funeral of a beloved neighbor. Homer regrets selling his Apple stock to buy a bowling ball, Marge worries she caused Bart's rebellious streak, Mr. Burns reminisces about a romance he gave up with a beautiful Parisian woman and Kent Brockman admits he was too afraid to leave local news and follow his former partner Rachel Maddow to cable news. Blackboard: 'We'll really miss you mrs. K.'