Jake draws a demeaning picture of one of his classmates (who has developed breasts earlier than the other girls) and faces expulsion from school. Alan has to meet with the Principal to argue for a reduced punishment, and gets Charlie to act as his receptionist for the day.
Tropes
- Boob-Based Gag: Jake's drawing of Barbara Schmidt, which features cartoonishly huge breasts that are certainly exaggerated.
- Brick Joke: After seeing Jake's 'Boobra Schmidt' drawing, Charlie says that he's hanging it on the refrigerator. The next day, when Berta asks what Jake did to get in trouble at school, Alan shows her the drawing...which is hanging on Charlie's refrigerator.
- D-Cup Distress: Barbara Schmidt becomes the target of mockery and teasing due to developing breasts before the other girls. Alan discusses the effect that large breasts can have on a woman's health.
- Didn't Think This Through: Jake signs the drawing he made 'Jake H' before passing it to another student, meaning that when it ends up in the hands of a teacher it's trivial to identify him as the artist. He admits later to regretting this.
- Digging Yourself Deeper: Alan meets with the mother of Barbara right before the meeting with the Principal, and tries to have a genuine discussion with her about what his son did, but between him not being able to stop himself from staring at her massive breasts and his inappropriate attempts to empathize with the 'plight' of the large breasted woman, it just makes things worse.
- Embarrassing Nickname: Barbara Schmidt, a preteen girl who has developed breasts early, is 'Boobra Schmidt' in Jake's drawing of her.
- Fiction Business Savvy: Charlie, having drank an unhealthy amount of coffee so he can be awake at Alan's office, comes up with an idea to sell donuts out of the trunk of a car during gridlock traffic. Alan is unamused.
- Happy-Ending Massage: Implied to be what the masseuse Charlie hired to work at Alan's office is giving to the customers.
- Kids Are Cruel: While Jake probably wasn't intending to be mean towards Barbara with his drawing, this is certainly the ultimate effect. When Barbara sees the drawing she goes home in tears, and given that many of the other students saw it it can be safely assumed that she'll be mocked over it for quite some time.
- Let Us Never Speak of This Again: On finding out that Charlie turned his chiropractic office into a brothel, Alan decides that the less he knows about it the better, and just says he doesn't want to hear about it.
- My Eyes Are Up Here: Barbara's mother has to pull this with Alan twice.
- Off Screen Moment Of Awesome: Given that Jake was facing expulsion, the mother of the girl that Jake made fun of is pushing for the maximum punishment possible, and the Principal herself is a large-breasted woman, whatever Alan did to get Jake a mere three day suspension must have been pretty amazing.
- This Is Gonna Suck: Alan's unable to find common ground with Barbara's mother during their discussion outside the principal's office, so he says they'll just have to allow the Principal to decide what a fair punishment would be for Jake. The Principal comes out of her office...a large breasted woman. Alan mutters that Jake's going to get the chair.
