The Simpsons visit a Chinese restaurant, where Homer is hired to write Chinese fortune cookies after complaining that the current fortunes are unimaginative. One of his fortunes says "You will find true love on Flag Day". This cookie makes its way to Mr. Burns on, coincidentally, Flag Day. Eager for true love at last, Burns and a reluctant Smithers spend the evening womanising at a wealthy social gathering and a strip club. With mere minutes left in the day, Burns finds a cop ticketing his car, which he had parked in the middle of the road. After discovering the cop is a beautiful woman named Gloria, Burns asks her out on a date. Gloria warily accepts, much to Burns' delight and Smithers' chagrin.
After a pleasant first date at the carnival, Burns asks about another date but Gloria is about to turn him down when Homer runs by. Burns asks Homer to vouch for him to Gloria, so Homer regales her by listing Burns' many exploits. After Gloria agrees to a second date, Burns enlists Homer to be his "youthful advisor", accompanying the couple on their next date at the disco hall, and even carrying Burns and Gloria up the stairs when they go to have sex. In these cases, Burns overcomes his weakness and extreme age by means of a powerful aphrodisiac (made from an extract of the "pocket fox", a species which only existed for three weeks in the 16th century).
Eventually, during a date at the bowling alley, Burns decides to ask Gloria to marry him. She says yes. As Burns goes off to get some champagne to celebrate, Snake comes to rob the bowling alley, and is surprised to see Gloria, who turns out to be his ex-girlfriend. Despite Gloria's protests, Snake kidnaps her and Homer. When Burns finds Gloria's ring, dropped in the commotion, he assumes she ran off with Homer. Snake takes Gloria and Homer to his hideout. Though Gloria says she loves Burns, Snake vows he can change. The police arrive and confront Snake. Homer tries to escape but instead sets Snake's house on fire. Snake and Homer get out and Burns runs in to save Gloria, however he is soon overcome by the smoke and Gloria is then seen carrying him to safety. Although initially grateful, Gloria begins to reminisce about Snake, causing her to break up with Burns and become Snake's girl again.