- Ted gets Lily a job at his firm, but she only makes trouble for Ted when he refuses to stand up to his boss. And Barney sleeps with Marshall's law school professor to help his grades, but she's less than impressed with his prowess.
- Lily is still trying to find her passion in life after returning from San Francisco. In order to do that, she will have to work somewhere - anywhere - to finance it. After a failed waitressing job, Ted offers her a job as an office assistant with his company. When she arrives at the office, she meets the head architect, Hammond Druthers, who she considers an inconsiderate blowhard who treats Ted like a child, and who is not a very good architect to boot. Lily uses a technique from her kindergarten class to try and make Druthers a nicer person to work with. Meanwhile, Marshall is having a difficult time with one of his professors. She, he's guessing in her forties or fifties, just got divorced over the summer and is taking it out on the students. After learning that she is attractive, Barney makes it his mission to trap a cougar so that the cougar won't attack her students anymore.—Huggo
- Lily is having trouble deciding what she wants to do with her life. She tries different careers such as life coach, marine biologist, slam poet, beekeeper, singing in a punk rock band. In the meantime, she is working at a Hawaiian restaurant where she has to wear a coconut bra as her work outfit. Her name is Anuhea (meaning cool and fragrant). She has to bring out a big Hawaiian drum every-time it is a customer's birthday. Ted offers her a job as a secretary at his architectural firm. Lily is put off by Hammond Druthers (Bryan Cranston), Ted's boss, because his designs are phallic.
Druthers is full of himself and extremely condescending to Ted and the other employees. Druthers berates Ted's work and compares him to his 6 yr old nephew who plays with Lego. He is assigned to design Styrofoam trees for the building model. Druthers says if Ted doesn't get the trees right, he will be fired. Druthers berates the trees that Ted designs. Lily learns from Robin that Ted has been working on his own design for the building. To punish Druthers, Lily "takes away one of his toys"-she steals his prized baseball "signed three times by Pete Rose". Ted finds the baseball in Lily's cabinet. Lily explains to Ted that her own form of justice works well on her kindergarten students (when they are mean to other students, she takes away their favorite toy till they learn their lesson) and that she even used it on a salesperson who was mean to Robin at Gap: she stole a pair of khakis that Robin gave to Ted. Lily calls them Justice Khakis.
Ted is horrified, even after Lily reminds Ted of how mean Druthers is (he didn't get his own mother a birthday present, threw a sandwich at the caterer for not having horseradish on roast beef, destroyed the ice cream cone of a young boy just to see him cry). And the next day, after finding the threatening note "from" his baseball that Lily left behind (in which Lily has anonymously offered to return the ball if Druthers started to be nice to others), Hammond angrily threatens to start firing people until the thief comes forward. Ted urges Lily to return the ball 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 (a major bank in financial services in Spokane, who wanted a modern skyscraper) 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 Lewis (Jane Seymour) at law school. She rarely gives good grades, and Marshall thinks she is taking her recent divorce out on her students; he mentions off-hand that she "just needs to get laid". Lewis is in her 40's. Barney calls her a cougar. A cougar keeps up with current hairstyles as a form of camouflage. It displays maximum cleavage possible to captivate the prey. The claws are long and sharp to ward off rival females.
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- (He didn't budget his time well, glossed over important points and overall presentation was sloppy & inconclusive). Barney sees her again, and she is still unimpressed (she revised her syllabus for the spring semester). Barney's third attempt resulted 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 (after 8 weeks of physiotherapy), but Marshall tells Barney to let her go; a cougar belongs in the wild.
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