Artie Ziff, now a tech billionaire, returns and offers Homer a million dollars if he agrees to spend a weekend with Marge so Homer can get money for an operation to help him stop snoring.

!! Tropes:

* EntendreFailure: When Marge arrives home via taxi after her evening with Artie goes sour, she instructs the driver to send the cab fare bill to "Baron Von Kiss-a-lot". However, that driver happens to be [[RecurringExtra the Wise Guy]], who proceeds to send the bill to a literal baron with GagLips.
* HaHaHaNo: After Homer suggests Dr. Hibbert perform his snoring surgery for free, Hibbert chuckles good-heartedly -- then tells Homer to GetOut.
* HomoeroticSubtext: While there are similar HoYay moments other times as well, this episode is ''heavy'' on the "gay couple" jokes about Lenny and Carl, or at least heavily implies that Lenny is in love with Carl.
* {{Jerkass}}:
** Artie Ziff. He offers Marge and Homer a million dollars to have Marge stay with him for the weekend and says that he won't try anything funny and then tries to anyway and then it's implied that he's spying on her through a camera in the mouthpiece that helps with Homer's snoring.
** Patty and Selma, who send an email to Artie Ziff by claiming to be Marge saying she wants to have sex with him.
* PetTheDog:
** Artie helping save Homer when he's about to die on an oil rig and admitting defeat to Homer. Somewhat subverted by the anti-snoring device having a camera and having anti-Homer messages.
** Homer when he thinks Marge wants to be with Artie.
* RichSuitorPoorSuitor: Artie Ziff and Homer Simpson.
* ShoutOut:
** When Marge leaves in the helicopter she see a message made from Homer using nothing but rocks, mirroring the famous final scene in ''Series/{{Mash}}'' (only the message on ''MASH'' said, "Goodbye," not "Keep Your Clothes On").
** The entire episode (and the title) is a reference to the movie ''Film/IndecentProposal''.
* StalkerWithACrush: Artie Ziff