Homer's new job as the author of fortune cookies assures Mr. Burns that love is on the horizon. Mr. Burns finds it in a woman named Gloria, whom he loves so much that he wants to marry. But as he proposes to Gloria, her ex shows up - which happens to be Snake, and he's just broken out of prison.
The Simpsons take in the sights and sounds of Chinatown and dine at a Chinese restaurant. As they finish the meal, Homer opens a fortune cookie and reads his fortune aloud. When Homer voices displeasure with his fortune, and informs the restaurant manager it doesn’t make any sense, he makes up some of his own. Impressed, the manager hires Homer to write fortunes. At home, Homer thinks up of a whole bunch of fortunes while Lisa is trying to type them up on a Chinese typewriter (which is mainly her poking the button 市). One evening, Mr. Burns orders a Chinese takeout. His fortune reads, “You will find the love of your life on flag day.” Inspired, Mr. Burns has Smithers accompany him for a night on the town. But their attempts at finding Burns a mate prove fruitless.
As the two men make their way back to Mr. Burns' car, he sees a police officer ticketing it. The officer is a woman named Gloria, and, finding her attractive and vivacious, Burns asks her out to dinner. Despite their age difference, Gloria accepts Burns’ offer to go out. But as the date progresses, Gloria has second thoughts about dating the old man. Thinking quickly, Burns tells Gloria that he and Homer are old friends who have enjoyed many youthful exploits together. Homer lists Burns’ various “accomplishments,” impressing Gloria and rekindling her interest. Later, Homer accompanies Burns and Gloria on their next date, which includes a stop at a disco bar. Burns and Gloria retire to the mansion, where Burns injects himself with a powerful aphrodisiac. Before Homer leaves the mansion, he injects himself with the stimulant, then returns home and makes love to Marge.
On their next date, Burns and Gloria go bowling. Homer again accompanies them. When Gloria sticks her fingers into a ball, she notices something unusual and pulls them out. On one of her fingers is a large diamond ring. Mr. Burns proposes…and Gloria accepts. A few moments later, Snake enters the bowling alley, gun in hand, intending to rob the cash register. Instead, he notices Gloria (she is Snake's old flame,) and insists they run off together. When Gloria refuses, Snake kidnaps her. Homer comes to Gloria’s rescue, but he is taken hostage as well, and the threesome drive off in Mr. Burns’ car. Snake takes Homer and Gloria to his hideout and gloria and homer are tied to their chairs and taunted, but police pinpoint their location thanks to a security device hidden in Burns’ vehicle.
As Wiggum waits out the crisis, he places some wintergreen Lifesavers in his mouth and then passes the mint around to his men. Sparks fly out of everyone’s mouth and Snake’s hideout soon catches fire. Burns decides to save Gloria himself. He injects the rejuvenating potion into his arm and races inside the burning building. He appears to have rescued Gloria, but then it is revealed that Gloria saved Burns. As Snake is rearrested, Gloria admits her desire for him and allows herself to be arrested too. Burns is disappointed as to how she couldn't love him, saying that he is "evil" as he walks down the road with the Simpsons.