The episode begins with Cam and Mitch sneaking in Lily’s room in the middle of the night because she has lost a tooth. They are planning to be the tooth fairy and leave something under her pillow, while she is asleep. They enter and see that she is still awake and waiting for the arrival of the tooth fairy. At the Dunphy’s, Phil is getting ready for career day, taking place at Luke’s school. At the Pritchett’s, Jay tells Manny the different jobs he had till he became successful. He says he always wanted to write a spy novel, but never got to it because he had to make money and support a family.
Gloria makes fun of Jay, saying she has been married to him for 5 years and not once did she hear him say he was interested in writing a book. At Mitch and Cam’s, Lily happily shows them what the tooth fairy left for her. Cam realizes that in the envelope that they put under her pillow, he left a $100 bill instead of a $5 bill because he had a bit too much to drink. Mitch isn’t too pleased about it and lets Cam know that in no uncertain terms. At Career Day, while Phil is giving the kids a presentation, Gil Thorpe, his rival realtor, whose kid also studies in Luke’s class, arrives.
Gil interrupts Phil’s presentation a number of times and eventually steals the show by handing out pickles to everyone. After Gil is done with his presentation, there is still a bit of time left, so the teacher asks Claire, who is there to assist Phil, to talk to the class. Claire reluctantly agrees, after the teacher assures her that being a stay-at-home mom is a very important job. While talking to the kids, Claire is constantly interrupted by one of the kids, who through her questions, makes Claire feel as if she is wasting away her life. Surprisingly, Gil springs to her defense.
At the Pritchett’s, Gloria places Jay’s old typewriter and a stack of blank papers in from of him, saying he wanted to write and now he can. Jay feels she is doing this because she is sure he won’t do it, so he decides to accept her challenge. At the school parking lot, Gil offers Claire a job at the new office he is opening. She tells him that she needs time to think about it, owing to the fact that he is Phil’s competitor. He asks her to take all the time she needs. At Mitch and Cam’s, they pretend in front of Lily that the tooth fairy has sent her a letter, asking for her $100 back because she made a mistake. Lily refuses to return the $100 and angrily walks away. At the Pritchett’s, Jay has begun writing, but after typing a few lines, his mind goes blank. He is simply not able to come up with anything and then things around him begin to distract him.
He makes himself a sandwich and gets back to writing. He drops some mayo on the keypad and while trying to clean it, ends up typing the letter “t” a number of times. At the Dunphy’s, Phil and Claire have a huge argument about the job issue. Phil feels Gil has offered this job to her only to get back at him, but Claire feels otherwise. He forbids her from working for Gil, but Claire makes it clear to him that it isn’t his decision to make. At the Pritchett’s, Manny returns home and sees Jay isn’t really doing a very good job of writing the book, so he helps Jay out by giving a few ideas. Manny even volunteers to type and asks Jay to move over. While he is typing, he orders Jay to get him some coffee. At Mitch and Cam’s, they bring in Haley, who is dressed as a tooth fairy, to convince Lily to give the money back.
Lily recognizes that the tooth fairy is actually Haley, despite the mask Haley is wearing. Haley then tries a different approach. She tells Lily that Santa will be mad if she doesn’t give back the money, which gets Lily thinking. Mitch and Cam are impressed that Haley managed to get through to Lily. While Phil is driving back home with Luke, he gets a call from Gil, who makes a bunch of inappropriate jokes, about how much fun he will have with Claire working “under” him. Phil decides to have a talk with Claire about this, before she starts working for Gil. At the Pritchett’s, Gloria returns home and Jay takes credit for what Manny wrote. Gloria begins reading what was written. When she criticizes the writing, Manny isn’t able to hold his silence and lets it slip that he wrote the whole thing, which embarrasses Jay and gives Gloria a chance to gloat.
After returning home Phil sees how excited Claire is about this new job, so he withdraws his objection. He tells Luke he is willing to handle a few lewd jokes from Gil, if this job makes Claire so happy. After thinking it over, Lily decides to return the money to the tooth fairy. Jay realizes his writing career is over, so he gets rid of the typewriter, but he is really impressed with Manny’s writing. At the Dunphy’s, a visibly enraged Claire returns home and tells Phil she quit. Claire couldn’t take the fact that Gil treated her like a servant and showed no respect. After consoling her, Phil asks her what’s for dinner, which pisses her off even more. The episode ends at this point.