The episode begins as Hank and his friends drink beer in the alley, Bill begins to sob. He tells the others that although he loves Christmas, the holiday marks the anniversary of his breakup with Lenore seven years ago. Hank follows Bill home, where he finds presents wrapped with fading paper. Bill admits that he has been saving the gifts for Lenore’s return. That night, Bill joins the Hill family for dinner. He raises the subject of breakups, causing Luanne, Bobby, and even Peggy to experience unpleasant memories. The next morning Bobby and Peggy ask Hank why Bill is allowed to ruin their dinners. Hank explains that some twenty years ago, Bill’s blocking allowed him to set Arlen High’s single season rushing record and for that, Hank will be forever grateful. The next day, Bill arrives at the Hill home in the company of his new pet iguana, which, not surprisingly in his depression, he has named Lenore. Bill disgusts the Hill family by putting a half-dead roach on the dinner table and watching as Lenore devours it. That night, Peggy tells Hank that Bill is no longer welcome at their dinner table. A few days before Christmas, Hank tells his friend that from now on, he and his family are dining by themselves. Miserable, Bill borrows (actually steals) Hank’s ladder, climbs onto his own rooftop with the intent to kill himself, and then jumps. The drop, however, is only about eight feet, and he survives.
Hank is concerned that Bill may find a more effective way of committing suicide. Peggy insists that Bill should be taken to a psychiatrist but Hank objects saying that Bill will be under constant watch until he snaps out of it. He, Dale and Boomhauer take turns monitoring Bill’s every move in case of trouble. Bill attempts halfheartedly to do himself in on several more occasions, but he fails. The schedule interferes with Hank’s much-needed rest. To help, Hank asks Peggy if she can find a date for Bill. Peggy invites Sheila Tobias to join Bill and the family for dinner. But Sheila quickly concludes that Bill has gone over the edge. Hank eventually loses his patience. He enters Bill’s home and begins destroying the old gifts meant for Lenore. Bill is numbed by the experience, though he assures Hank he is perfectly fine. Hank returns home, where he finds Lenore the iguana perched atop the refrigerator. Hank carries the creature into Bill’s backyard, where he encounters what appears to be a woman hanging clothes on a line. When the woman turns around, Hank realizes, to his horror, that it is actually Bill in a dress.
It is clear that Bill has finally snapped. Now speaking in a falsetto voice, Bill claims to Hank that he is actually Lenore. Hank turns and walks away, warning Bill not to show up for the party. But on Christmas Eve, Bill arrives at the affair wearing a dress, hat and necklace. Hank gasps at the sight and the guests are mortified. He then instructs Bill to leave the house at once. But Bill remains, insisting that Lenore loves a party. Just then the real Lenore telephones the Hill residence. But before Peggy has a chance to hand Bill the phone, Lenore hangs up. Bill breaks down, sobbing. The party-goers turn vicious and begin insulting Bill. Suddenly, Hank emerges from the bedroom wearing a dress, attempting to cover for Bill by announcing to everyone that 'it's that kind of party!', a confused Dale mentions this not being on his invitation. Bill runs outside, and Hank follows. Pretending to be Lenore, Hank tells Bill "she" no longer loves him. Bill gets angry and tells "Lenore" to get out of his life. With that, Hank removes the dress. A few moments pass, and Bill removes his dress as well. He returns to his senses, telling Hank he hit "rock bottom" for a while and that "it's all up hill from now on". With that, Hank wishes Bill a "Merry Christmas." From behind, Dale walks by wearing a dress but runs off when seeing Hank and Bill already removing their dresses.
- Hank Hill
- Peggy Hill
- Bobby Hill
- Luanne Platter
- Dale Gribble
- Nancy Gribble
- Joseph Gribble
- Jeff Boomhauer
- Bill Dauterive
- Buck Strickland
- Joe Jack
- Principal Carl Moss
- Jason Adderly
- Mrs. Tobbis (cameo)
Non Speaking Character
"Why do you keep calling me 'Bill'?" -Bill as Lenore
- Fans consider this to be the darkest episode in the series, especially since it took place on a Christmas Special.
- After Hank returns Bill's iguana Lenore to him, it is never seen again.
- When Bill is reminding Bobby of his ex-girlfriend, from the front all Bobby has on his plate is a small amount of unidentifiable red-coloured food, but from the back it is brown and in abundance.
- Bill has the couch from the alley from "And They Call It Bobby Love" in his house, as shown in the ending phone call sequence of "And They Call It Bobby Love".
- When Bobby is putting food on the plates at breakfast, he is shown to have three eggs and three slices of bacon. He then places one egg on Hank's plate and two on Peggy's plate. But, after Hank says "Shame on you, shame on you both.", Bobby is shown to still have one egg left.
- Luanne mentions Buckley's angel telling her about closure as she, Hank, and Peggy are discussing Bill's mental breakdown; however, Buckley's angel doesn't make an appearance until the episode "Wings of the Dope", episode 58 (season 3, episode 23) of the series.
- In the episode The Son That Got Away (Season 2, episode 8) Bill mentions being made to wear dresses as a punishment from his father. Immediately afterward, he wistfully sighs "Pretty, pretty dresses," dropping the episode title.
- Peggy mispronounces the word "iguana" by saying "i-JOO-won-uh" instead of "ig-won-uh."
- Bill breaks his arm when he falls off his roof. However, Hank is able to jump off his own roof without an issue, even with both roofs being the same height.
- Bill is showing trying to kill himself throughout part of the episode. However he obeys Dale when he threatens to shoot him with a shotgun.
- This is the first episode to mention the name of Bill's ex-wife, Lenore, and that she left him 7 years prior.
- This is one of only two episode to ever show Hank's set of ladders mounted in the garage, the second being Naked Ambition, in which Bobby uses Hank's "ten footer" that same used in this episode. Also, when Bill is seen walking away from the garage with Hank's ladder, it's briefly shown as still being mounted on the wall among the other ladders, however when Hank enters the garage, it's clearly missing. Furthermore, when Hank rushes over to Bill's house when he suffers the fall off his roof, a brief shot of the garage shows the garage absent of all the ladders.
- When Boomhauer grows tiresome of watching Bill. he complains of having no time between work and keeping an eye on Bill. This is the only mention of Boomhauer working or having a job until it's revealed that he's a Texas Ranger in the season 13 finale To Sirloin With Love.
- At Hank's Christmas party, Ray is seen among the guests along with Enrique and Joe Jack.
- When Bill is seen inside 'Uglys: A Cowboy's Salon', the instrumental sounds very similar to the song "You're The One" by Dwight Yoakam. The first few lyrics of the song is very similar in Bill's situation and Yoakam was also a voice actor on the show as recently as two episodes ago in 'Nine Pretty Darn Angry Men', voicing Lane Pratley.