Summary: Lily takes a job at Ted's architect firm, but causes more harm than help when she tries to punish his boss for being rude. Meanwhile, Barney tries to make his moves on Marshall's law professor.
However, at her first day at work, Lily is immediately put off by the obnoxious antics of Ted's boss Hammond Druthers, who is fond of designing phallic buildings and is unpleasant towards his employees (especially Ted, whom he relegates to making fake trees for the building's scale model despite being a trained architect). Annoyed at Ted's unwillingness to stand up for himself and his fellow employees, Lily decides to steal Druthers' favorite "toy", a baseball signed three times by Chicago Cubs legend Pete Rose. Ted later finds the ball at her desk drawer and calls her out of it later at the bar, but Lily justifies her action, as it is the same method she uses to discipline her students back when she was still a kindergarten teacher.
Meanwhile, Marshall confides in with Barney his problems with his recently-divorced law school professor, who is taking out the stress from her divorce on her students.
A grateful Ted tries to offer the job back to Lily, but Lily politely refuses, as she has realize what her passion in life really is: teaching in kindergarten.
Later, the gang visits Barney in the hospital, who had dislocated his hip after vigorous sex with Marshall's law professor. A determined Barney promises Marshall that he "will get him an A" after he gets discharged and finishes two weeks of rehabilitative therapy, but Marshall stops him, saying that "A Cougar belongs to the wild"
The episode provides examples of:
- Compensating for Something: Lily suggests this about Ted's boss's building design.
- Doomed Autographed Item: Lily is so appalled by Hammond's behavior to people that she decides to start taking away his things. It's her personal form of justice, supposed to make kids and people stop being mean. The first thing she takes away is Druthers' baseball signed three times by Pete Rose. He's livid, and threatens to start firing random people if his ball is not returned.
- You Are Fat: Ted is making at least twice fat shaming comment about an ex co-worker he morally destroyed earlier.
- Gag Penis: Druther's building proposal has a round-coned top, two domes at the base and covered with brown trees.
- Fleeting Passionate Hobbies: Lily has had been teaching in kindergarten, so she set up to find out her passions. In sequence, it had been a life coach, a marine biologist, a slam poet, a bee keeper, not a bee keeper, and singing in a punk band while waiting tables at a Hawaiian-themed restaurant.
- Innocently Insensitive: Ted unintentionally made an obese co-worker quit her job due to her bringing lunch worth for everyone at the office.Marshall: Dude, that is cold-blooded.Ted: It was an honest mistake. Look, when somebody opens up a container with an entire chicken in it, it's okay to assume they made lunch for everyone.Robin: Ted, that girl didn't quit. You destroyed her.Ted: It was a whole chicken. And did I mention she had 12 sides?Barney: Oh, now you're gonna bash her figure. Real classy, Ted.
- Misplaced Kindergarten Teacher: Pretty literally. Lily treats conflict resolution between Ted and his boss exactly like she does in her classroom.
- Mrs. Robinson: Marshall's professor, the cougar.
- New Jobs As The Plot Demands: Lily, first as a waitress at Big Wave Luau, then as an assistant at Ted's office.
- Sadist Teacher: Marshall's professor is bitter over her divorce and won't give out grades higher than C+. Barney sets out to tame her.
- Shout-Out: When Lily is describing Druthers' "mean" actions, the last one, when he knocks the ice cream out of a little boy's hand, Druthers starts acting like Scut Farkus from A Christmas Story. Then she admits that she "might have made that last one up."
- The Unreveal: We never get to see the penis building; its unveiling is hidden by a pillar.
- Woman Scorned: Marshall explains his professor is being harsh on the students because she's bitter over her recent divorce.
