Comedy writer Liz Lemon lives every comedy writer's dream as the head writer on a demanding, live TV variety program in New York City, which stars one of her closest friends, the sweet, but self-absorbed Jenna Maroney.
Now that major changes have occured on the The Girlie Show, Liz struggles to bring everyone and everything together. However, despite his erratic behavior, Tracy manages to bring everything to order.
Confident he can fix both Liz Lemon's sketch show and sex life, overbearing boss Jack sets Liz up on a blind date with his friend Thomas. With Liz readying herself for her blind date, Jack infiltrates the writers' weekly poker game.
As Kenneth the Page quickly learns working for Tracy Jordan may be more than he bargained for, Liz struggles to keep ego-maniacal Jack out of the writer's room and the scantily clad Cerie in her clothes.
When Jack pressures the writers to plug GE products, Liz decides to integrate Jack himself into a sketch. Jack brushes up on his acting skill, while Frank and Toofer are busy tricking Jenna into thinking she is on the verge of being fired. While Jenna fears for her job, Liz wonders if Tracy is faking illiteracy to skip out on rehearsals.
Liz confesses she got back with her ex, because he asked. Jack Donaghy fears that Liz is leading a life of mediocrity and takes it upon himself to be her mentor. Meanwhile, back at the show, Liz needs to deal with a physically-altered cast, including a face tattoo on Tracy; botox and collagen injections on Jenna and Josh sporting two black eyes from a run-in with an angry Regis Philbin.
Jack Donaghy bumps Jenna Maroney's scheduled appearance on 'Late Night with Conan O'Brien' by booking new star Tracy Jordan. Jenna, still irate over watching the show change to "TGS with Tracy Jordan," lashes out at Liz.
Liz finally breaks up with Dennis and hits the singles scene under Jenna's guidance. Jack hits a rough patch in his relationship. Toofer and Tracy are sent to sensitivity training classes.
When the clueless teenage receptionist Cerie announces her sudden engagement to a wealthy Greek heir, Liz contemplates her own marital - and maternal - future, while the seemingly unbreakable Jack crumbles underneath the weight of his own issues.
While Jenna anxiously awaits the limited release of her indie film, "The Rural Juror," Liz and the writers are loathe to confess they can't even grasp the tongue-twister of a title. Meanwhile, Tracy, desperate for some financial help-heeds Jack's advice and creates his own celebrity product to endorse.
Intrigued by two MSNBC guys - the cerebral nerd "The Head" and the gorgeous hunk "The Hair" - they keep running into inside 30 Rock, Liz and Jenna decide to get serious about their dating lives, but find themselves unexpectedly switching their typical roles when Liz admits she's clicking with - and falling for - The Hair.
Liz wonders if she's actually on a date with Jack as she accompanies him to a birthday celebration for a foreign prince. While at the ball, Liz sees a different side to Jack as he unexpectedly runs in to his ex-wife. Back at 30 Rock, Tracy tempts Pete with a booze- and babe-filled party in the office, while Kenneth the Page tries to keep Pete on the straight and narrow.
The crew must pull an all nighter on Valentine's Day. Pete forgets the holiday. Kenneth wonders if Cerie is interested in him. Liz receives flowers from a secret admirer. Jack wants to celebrate his divorce with Tracy, who wants a night alone with his wife.
After being a bit harsh on Lutz in the writer's room, Liz overhears him criticizing her iron-fisted management with the use of the "C-Word". Realizing she has to be more lenient with her staff, Liz adopts a more lax leadership style.
When Josh's contract is up, Jack sees an opportunity ripe for cost-cutting. While Liz tries to keep Josh in the 'TGS' cast and from jumping to a rival show, Tracy awards Kenneth the Page a coveted spot in his entourage. Meanwhile, Jenna gets into some hot water over a misquote in a popular magazine.
Jack, who needs to unload his family's staid and sub-par line of wines, persuades Ghostface Killah and hip-hop producer Ridikolus to endorse "Donaghy Estates" and introduce the next Cristal. Meanwhile, Kenneth the Page catches the eye of Ridikolus's girlfriend while attending The Source Awards with a reluctant Tracy. Liz attempts unsuccessfully to break up with Tracy's business manager.
Jack helps his brother Eddie with a job at 'TGS', but can the staff handle him? Meanwhile, Liz, forced to make staff cutbacks, wonders if axing NBC lawyer Floyd's girlfriend, Over Liz would look desperate. Tracy seeks spiritual fulfillment at his lawyer's request with the aid of Kenneth the Page.
A seedy network executive from the west coast arrives to make a play for Jack's job. Jack tries to use Kenneth to seduce him and find out his secrets. Tracy is served with paternity papers. He turns out not to be that father of the child, but discovers that he is a direct descendant of Thomas Jefferson. Liz pretends to be an alcoholic to get to know Floyd better.
The tables have turned inside 30 Rock, Liz is actually happy in her new relationship with Floyd while Jack finds his job may be in jeopardy after his televised fireworks fiasco prompts top GE man Don Geiss to warn he's got his eye on Jack's performance and strips him of his microwave division responsibilities.
Sick of New York and frustrated with his career, Floyd contemplates a move to the Midwest and asks Liz if she would consider leaving TGS behind. Jack rushes to Paris - and soon to the altar - with Christies' auctioneer Phoebe. Meanwhile, Tracy works furiously on financing his latest career move, dubbed the "Tracy Jordan Comeback."
As TGS' summer hiatus approaches, Liz deals with the difficulties of her long-distance relationship with Floyd while she enlists Kenneth's help in locating on-the-lam Tracy. Meanwhile, Jack's impending marriage to Phoebe brings his mother, Colleen Donaghy, to town. This lead to a heart attack and a realization that he doesn't love Phoebe but he does love his work, and renewing his dedication to it.