Bobby takes his break-up with Connie hard after Bill tells Bobby that he ruined his one chance at love, and, after a deep depression, Bobby gets advice from Boomhauer on how to win over girls.
Tropes:
- Amicable Exes: Bobby, having just broken up with Connie at this point makes it clear to Bill initially that the two are still good friends. Naturally, he's not hearing any of it and ends up convincing Bobby that she's just lying to him.
- Anti-Role Model: Peggy describes Bill as such to Bobby and she has a point given he drove Bobby into a depressive mess after staying with him. She is further displeased when she finds out Hank let Boomhauer take Bobby out cruising for girls.
- "Could Have Avoided This!" Plot:
- Had Bobby never let Bill in while Hank and Peggy stepped out, he would never have resorted to dressing like a cupid and crashing Joseph's party in a desperate attempt to win Connie back or attempted to learn how to pick up chicks with sexually-charged innuendos from Boomhauer.
- Peggy is also guilty of this for even asking Bill to check up on Bobby every now and then even though she trusted him to handle himself without a babysitter for the first time, knowing how easily he goes overboard when given even the slightest amount of responsibility and later stating that anyone who spends too much time with Bill turns into another Bill.
- Idiot Houdini: Bill doesn't even get so much as a calling out by Hank or Peggy after ruining Bobby's life. Not that Bill would have listened, mind you.
- Irony: Joseph wonders if he behaves so pathetically around girls when Bobby is a love wreck.
- Moment Killer: Hank disrupts Boomhauer's moment in being led by a woman who did show interest into the fitting room thinking he's going into the women's one by mistake.
- Sanity Slippage: Bobby descends into love insanity the longer the episode goes.
- Shoe Size Angst: When Hank and Peggy find Bobby having a good time with his new friend Debby, Peggy tries to avoid answering Bobby why they're at the shoe shop by asking out loud if they have shoes at size 16.5. Debby laughs, thinking Peggy was joking. Peggy is not amused.
- Stalking is Love: Bill leads Bobby into doing this, ending up with the boy crashing Joseph's party while dressed as cupid trying to get Connie back.
- Squick: In-universe. Everyone at Joseph's party has this reaction when they see Bobby dressed as cupid.
- Terrible Pick-Up Lines: One of the things Boomhauer teaches Bobby in an attempt to get chicks is to use pickup lines. Every single one Boomhauer says gets instantly shot down and by Bobby's count, he got turned down 27 times before he finally managed to get a single woman's phone number.
