Lily is having trouble deciding what she wants to do with her life. In the meantime, she is working at a Hawaiian restaurant. Ted offers her a job as a secretary at his architectural firm. Lily is put off by Hammond Druthers, Ted's boss, because his designs are phallic and he is abusive to his employees, especially Ted. When Ted finds Hammond's prized baseball that was autographed by Pete Rose in Lily's desk, Lily admits to Ted that she has been taking things from his boss in order to teach Hammond a lesson. She tells Ted that it is her own form of justice, and it is based on her experiences teaching kindergarten, taking toys away from kids who misbehave. Hammond is furious that his baseball is missing and threatens to fire three people an hour the next day until it is returned. Lily thinks that his threats are empty, and tells Ted that she will return the baseball if Ted shows Hammond his re-design of the phallic skyscraper. Ted refuses, firing Lily instead. The next day, the firm's client turns down Hammond's design because it looks like a penis. In order to keep the client from walking out, Ted presents his own design of the building. Ted's design is approved, and he is credited with probably being the youngest architect to design a building taller than 70 stories. Ted offers Lily her job back, but she tells him that she has realized her true calling is as a kindergarten teacher.
Meanwhile, Marshall is upset with a particularly difficult professor at law school. She rarely gives good grades, and Marshall thinks she is taking her recent divorce out on her students; he off-handedly mentions that she "just needs to get laid". Barney, seeing this as a challenge, decides to help Marshall by seducing the professor, but is thrown for a loop when she gives his sexual performance a grade of C-. Barney sees her again, and she is still unimpressed. Barney's third attempt results in a dislocated hip, but the sex was good enough to get Marshall a B+ on his paper. Barney wants to try to get Marshall an A, but Marshall tells Barney to let her go; a cougar belongs in the wild.
Reviewer Joel Keller notes that guest stars can upset the style of a comedy and of the two guest stars in this episode he felt Bryan Cranston was wasted as Ted's boss, but was impressed how Jane Seymour's character challenged Barney.