When Boomhauer is on the receiving end of being humped and dumped, he falls into an incurable funk.
Tropes:
- Armor-Piercing Question: To lift Boomhauer's spirits, the guys decide to take him out to look for ladies. Peggy objects to Hank glorifying Boomhauer's "tomcatting," until Hank cuts her off.Peggy: If you think for one second that I am gonna stand by while you go on a floozy hunt for Boomhauer-
Hank: [sigh] Peggy, do you want another Bill on your hands?
Peggy: [look of horror, before grabbing her keys] Take my car. It's a chick magnet. - Bait the Dog: Marlene was thought by Boomhauer to be a sweet, wealthy woman to the point that he plans on proposing to her with his grandmother's wedding ring. Then as it turns out, Marlene wasn't the woman he thought he was but basically a mirror of himself, only worse.
- Brick Joke: Boomhauer's bedroom plays music by Dido whenever he is in bed with a woman which happens when Boomhauer took Marlene to bed much to Bill's dismay to the point of begging him to not play Dido. After Bill takes Boomhauer from his bed so he can help him get over his breakup, Hank and Dale leaves the bedroom before turning off the lights... which also plays Dido complete with disco ball.
- Break the Haughty: After years of loving and leaving women, Boomhauer finds it's not so fun when it happens to him.
- Halfway Plot Switch: Subverted. The episode initially begins as a Bill-centric episode before becoming a Boomhauer-centric episode, and Bill is brought back into focus by helping Boomhauer get over his breakup.
- Kick the Dog:
- As Boomhauer calls through Marlene's office phone to beg her to take him back, Bill points out that he heard laughter as she purposely aired it out to her co-workers through the speakerphone.
- The episode as a whole serves as one to Boomhauer after the breakup.
- Laser-Guided Karma: After some encouragement from Dale, Bill and Dale decide to create potholes in street so Bill can take the woman to his house and give her first aid so she’ll be attracted to him. While she does fall in one of the holes, when Bill tries to help the girls, he ends up falling in 4 holes and then Boomhauer comes around to take her for himself.
- Like Parent, Like Child: Boomhauer goes to get his grandmother's wedding ring to propose, and of course, his grandmother is every bit the garbled Motor Mouth that he is.
- Must Make Amends: Having been on the receiving end of being loved and left, like he'd always done to tons of women, Boomhauer seeks out the ice cream lady he did that to at the beginning of the episode, and apologizes profusely.
- Out-of-Character Alert: When Bill of all people is picking on Boomhauer for being heartbroken due to Marlene doing the same thing to him like he did to other women he had flings with, even Peggy is shocked."Bill is picking on Boomhauer? He hasn't done that since he had hair."
- "Ray of Hope" Ending:
- Bill gives himself one. Not only did he get screwed out of a shot with that girl thanks to Boomhauer, it's not likely he had much of a shot anyway... but the episode ends with Bill outside a ladies' prison, with a bundle of flowers, looking to try and get lucky again. Bill may be a broken sad sack of a man, but he's still putting himself out there.
- In Boomhauer's case, he looks like he has a better sense of perspective on his dating life after having his heart broken, and he starts by making peace with the girl he blew off early in the episode.
- Rousing Speech: It's Bill of all people, who has a lifetime of experience with romantic rejection, who gets Boomhauer back on his feet.Bill: I know how dark it is for you right now, curled up, lying in your own emotional vomit. You're in hell now Boomhauer, and the only way out is through a long dark tunnel. And you're afraid to go in, because there's a train coming at ya, carrying a box car full of heartbreak. Well let me tell you something, all you can do is let it hit you, and then try to find your legs. Mm-hmm. I know, I've taken that hit more times than I can remember. Look at me, Boomhauer. I'm fat and I'm old, and every day I'm just gonna wake up fatter and older! And somehow, I manage to drag this fat old bald bastard into the alley every day. I'm out there, digging holes, falling into them, climbing out, trying again. And tomorrow, I'm gonna hang outside at a ladies prison. And the first thing those lady cons are gonna see after twenty years, is me. Will I get one? Experience says no. Will I be out there next month? If I'm alive, you better believe it. (Grabs Boomhauer's shoulder, his voice getting steadily louder) You gotta get back up on that tanning bed, slip into a tight T-shirt, wash off some of that cologne, and get yourself out of that tunnel, and into some strange woman's bed!
- Special Guest: Laura Linney as Marlene.
- The Unintelligible: Boomhauer's grandmother is this even to him, at least until she puts her teeth in. At which point she's still The Unintelligible, but he can understand her.
- Vitriolic Best Buds: Bill gets upset with Boomhauer landing Marlene first instead of him which led to the conflict between them for the episode. After Boomhauer gets his heart broken by Marlene, Bill even teases him about it since he had it coming for all the women he did the same to by treating them as flings. After witnessing how broken Boomhauer was when driven back home to his bed, Bill of all people goes to aid him and help him get over his heartbreak by telling from his experience which heals their friendship and gets Boomhauer back on his feet.
