Marge is irritated when Homer's snoring (so loud, it can be heard through most of the city) keeps her up at night. She sees Dr. Hibbert about the problem, and asks about a surgery, but he says it is expensive and tells them to get out when Homer asks him to do it for free. Developing a sleep problem, she sleeps for a night with Patty and Selma, and hears on the news that her old boyfriend, Artie Ziff, is one of America's five richest people. She drunkenly dictates an e-mail to Artie to congratulate him on his appearance, but Patty and Selma doctor it to use sexual terms in an attempt to split up Marge and Homer, much to Marge's horror (for using the word sex on the Internet). Artie, who over the years seems to have developed a rather frightening obsession with Marge (his house is decorated with a large number of 'Marge' sculptures/paintings), flies in his helicopter to the Simpson house to see Marge.
After arriving, Artie offers Marge a $1 million proposal to spend a weekend with him, just to see what life would be like if they were married. Marge initially rejects the offer, but eventually can no longer stand Homer's snoring. She chooses to spend the weekend so she can get the money for the surgery. They have a good time until Artie tricks Marge into making out with him against her will in a reenactement of their prom during the 70's made to mirror the one they attended in "The Way We Was" (with even its original attendants who were paid by Artie to show up disguised as they were at that time). Homer, having just anxiously arrived to check up on them, sees Artie kissing an unwilling Marge and, unaware of the true premises, is devastated, and leaves with Lenny away from Springfield. Lenny seems similarly dejected about his relationship with Carl; he and Homer get a job in an oil field in West Springfield, a likely death spot for the two of them. On the way there, they discuss the loves they left behind. All cacti resemble Marge to Homer, and Lenny mournfully points out the image of Carl that he carved on a mountain one blissful summer. Meanwhile, Marge leaves Artie furiously, only to discover what Homer had done when she gets home. She finds he is not there and that he had left a tape behind.
While working on an oil rig, Lenny and Homer accidentally set fire to an ant, who in turn sets fire to all her ant companions, who jump in a puddle of oil to extinguish the flames. Their brief sighs of relief are replaced with screams as the whole rig catches fire. Marge go with Artie along with Carl to West Springfield to save Homer and Lenny. At first, they are reluctant, as Homer still thinks that Marge and Artie are having an affair, and Lenny feels that there is nothing for him in Artie's helicopter. However, Artie finally admits defeat to Homer, saying that winning Marge's love was something that he could never accomplish, even with his billions, and Homer jumps on the ladder to the helicopter. Carl reveals that he is in the helicopter, and Lenny also jumps on to be saved, just before the rig collapses. Homer and Marge's marriage is also apparently saved when Artie offers a solution to Homer's snoring problem, a device which converts snoring to music. However, Artie's voice is soon heard through the device's speaker, giving Marge anti-Homer subliminal messages and eventually saying that he is watching her through a camera.