- Liz feels uncomfortable when she joins her unusually handsome boyfriend in "the bubble," Tracy decides to quit the show rather than negotiate a new contract, and Jenna tries to have her hair cut for publicity and attention.
- Open with Liz leaving the office to have lunch with boyfriend Dr. Drew Baird (Jon Hamm). On her way out Jack tells Liz that Tracy's contract is up and he is handling the negotiations personally. Jack isn't concerned given Tracy's vast personal fortune and their close relationship.
Walking down the street it becomes clear just how good-looking Dr. Drew really is: Strange women stop him to tell him how great he looks, a traffic cop tears up his ticket, and Calvin Klein asks him to be an underwear model.
Liz comes in to the office and tells Jack how strange Dr. Drew is being treated. Jack tells her that really good-looking people like him and Cerie live in a special bubble. Showing her a picture of himself when he was 25, Jack tells Liz that the window isn't always open and she should enjoy being in there with him.
Jenna tells the staff she plans to get her haircut on The Today Show that Friday and donate it to charity, primarily to help generate the kind of buzz Tracy has been getting.
Though Tracy almost instantly agrees to a new contract and small raise, Jack happens to mention that Tracy has enough money that he doesn't really have to work. Never having thought of it that way, he instantly quits.
Through a montage of scenes we see that Dr. Drew is terrible at just about everything: sports, cooking, sex, being a doctor... but is completely unaware of his shortcomings.
Jack tells Liz that the "danger of being super-handsome" is that nobody ever tells you the truth. Liz plans to tell Dr. Drew and Jack warns her to be careful: "When you wake a sleep-walker you risk getting urinated on." Kenneth spills the beans to Liz that Tracy has quit and she relishes in the glory of Jack being the one to screw-up.
Jenna emphasizes to the staff just how important to a career a haircut can be.
Jack calls Tracy and has a member of the accounting department pretend to be Bill Cosby asking him to return to the show. It does not work.
Liz begins the process, forcing her and Dr. Drew to wait in line for a table rather than let him talk to the hostess.
Tracy's sons Tracy Jr. and George Foreman tell Jack he has to get Tracy back to work. Tracy is terrible at packing lunches for the kids ( (jar of mayonnaise and cigarettes) and has built a recording studio in the rec room.
Liz tells Dr. Drew he has been living in a good-looking bubble his entire life. He responds that he would like her to be honest with him. We cut to Liz kicking Dr. Drew's butt in tennis. He eventually slams down the racket in disgust: "You're a cheating bitch!"
Kenneth tells Jack that he is still helping Tracy in his personal life: "Tonight I have to ride my bike over to his house in New Jersey to hold his hand during 'Lost.'" Jack realizes that Kenneth is the network's best bargaining chip and tells him to cut Tracy off.
Liz seems conflicted as to whether tell Dr. Drew was a mistake.
Kenneth has been using a British-accented character named Cranston to avoid Tracy's calls. Kenneth doesn't know how much longer he can keep ducking Tracy but Jack promises he'll eventually cave and come back to work.
On The Today Show Jenna tells Meredith Vieira that she was turned down by Locks of Love and is donating her hair to "Merkins of Hope." During the cut Vieira tells her Tracy has quit the show and suggests she is now the only star left. Jenna stops the haircut and runs off the stage.
Three hours before the show Tracy shows up at the studio to get a few things. Kenneth breaks down and tells Tracy what they've been doing and starts to leave with Tracy. Jack fires Kenneth, which forces Tracy to return on the condition Kenneth continues to be a page.
Dr. Drew apologizes for how he acted and tells Liz he wants to stay in the bubble and to have her with him. Liz says she doesn't think the relationship will work out.
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