After getting his coworkers in trouble for stealing office supplies, Homer begins wetting the bed. Thinking this is Laser-Guided Karma for what he did, he tries to atone — only to continue peeing in his sleep. With the help of Professor Frink, the Simpsons go on an Inception-style journey to Homer's dreams to find out why he's been wetting the bed.
- Always a Bigger Fish: As the Grim Reaper falls off a cliff, he realizes that, as the personification of death, he can't die, only to be proven wrong when a bigger, scarier Reaper comes in to claim him.
- Animal Testing: Inverted: Frink claims he let the Simpsons borrow his dream exploration machine so that he can find out if it's safe to use on monkeys.
- Arson, Murder, and Jaywalking: Homer's dream is falling, Marge's dream is drowning of fish, and Lisa's dream is having tomatoes thrown at them.
- Bait-and-Switch Comment: Once atonement for how Homer screwed his coworkers didn't stop him from wetting his bed, he drew a knife and said it was time for drastic measures. He cut open the plastic wrapping of the yellow pages. (Or, as it's known in-universe, the internet for old people)
- Cast as a Mask: Death/the Grim Reaper appearing in Homer's dream has a gruff masculine voice by Chris Edgerly, but later on "he" unmasks to reveal Mona Simpson, voiced by Glenn Close. Justified in that it's really a dream.
- Freudian Excuse: For Homer's bed wetting: turns out that when he went fishing with Bart, it reminded him of the time he went fishing with Abe as a child and tipped the boat over, forcing Abe to rescue him, which he thought was the final straw in having Abe and Mona get divorced a week later.
- Grim Reaper: Appears in Homer's first dream. When the family goes over the side of the mountain, the Reaper joins them and is screaming alongside them before remembering he can't die... and then turns around and sees a gigantic, beastial reaper with wings flying beside him and roaring like a dinosaur. The first reaper is understandably scared shitless.
- Latex Perfection: After Death/the Grim Reaper saves the family in one of Homer's dreams, "he" peels off his rubber skull mask, revealing itself to be Mona Simpson, who lives on in Homer's dreams.
- Lost in Translation: When translated into Brazilian Portuguese, "met" and "wet" (as in "urinated on," not the adjective meaning "covered or saturated in liquid") become respectively "conheci" and "molhei". The translators used the first and completely killed the pun.
- Magic A Is Magic A: When in a freefall, Lisa suggests going deeper into another dream for time dilation reasons.Bart: "Dreams have rules?"
Lisa: "Everything has rules!"
Bart: "You haven't seen me when I dance!"
- Meet Your Early Installment Weirdness: In one of the dreams, the Simpsons act and look as they did in the early The Tracey Ullman Show shorts.
- Pun-Based Title: The title is based on the sitcom How I Met Your Mother.
- Recursive Reality: The family enters several dreams within the initial dream.
- Shout-Out: When Homer tries to ditch his family in the dream based around his gluttony, he yells he's never going to leave and boards a rollercoaster called "Mr. Homer's Wild Ride".
- Whole Plot Reference: Despite the title being based on How I Met Your Mother, the episode plot is similar to Inception.