Liz Lemon is the head writer on The Girlie Show, a demanding, live TV program in New York City. However, things begin to get complicated when her new boss insists that a wild and unpredictable movie star joins the cast.

Now that major changes have occurred on The Girlie Show, Liz struggles to bring everyone and everything together. However, despite his erratic behavior, Tracy manages to bring everything to order.

Jack sets Liz up on a blind date with his friend, Thomas. While Liz is busy preparing for the date, Jack infiltrates the writers' weekly poker game.

Liz struggles to keep Jack out of the writers' room, and Kenneth learns that working for Tracy may be more than he expected.

After being pressured by Jack to plug GE products into her show, Liz integrates Jack himself into a sketch. While Jack hones his questionable acting chops, Frank and Toofer trick Jenna into fearing for her job, and Liz wonders if Tracy is faking illiteracy to skip out on rehearsals.

After Liz takes her ex-boyfriend, Dennis, back simply because he asks, Jack takes it upon himself to mentor her as he thinks that she is leading a life of mediocrity. Meanwhile, Tracy gets a tattoo in the face, Jenna gets botox and collagen injections, and Josh is given two black eyes by an angry Elizabeth Taylor.

Jack bumps Jenna's scheduled appearance on Late Night with Conan O'Brien by booking new star Tracy. Jenna, still irate over watching The Girlie Show change to TGS with Tracy Jordan, lashes out at Liz. To make matters worse, Tracy's gone off his medication, and he's about to go on national television.

When Liz finally dumps her boyfriend Dennis, she prowls the singles scene under Jenna's tutelage. Love also stinks for Jack, as he discovers dating a Bush administration official has its downside. And Tracy and Toofer clash, which lands both in sensitivity training.

When ditzy receptionist Cerie spreads news of her engagement to a filthy rich Greek heir, Liz confronts her own marital and maternal status. Meanwhile, emotionally hardened Jack softens due to mommy issues.

Jenna anticipates the opening of her independent movie, The Rural Juror, but the title proves to be a mighty tongue twister for the gang. Meanwhile, cash-challenged Tracy endorses his own celebrity product in an effort to get out of debt.

Liz and Jenna work on their dating game when they're beguiled by two very different MSNBC staffers—a brainy geek and a brawny hunk. Cerebral Liz finds it strange that she's more interested in the attractive one. Meanwhile, Kenneth and Jack switch roles.

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 tries to keep Pete on the straight and narrow.

It's Valentine's Day, and the TGS crew is celebrating by pulling an all nighter to put together a new episode. While Pete completely forgets the holiday, Kenneth and Cerie may be starting an office romance. Meanwhile, Liz wonders if Dennis is back in her life after she receives flowers from a secret admirer, and newly divorced Jack wants to party with Tracy, who for once wants to spend a night alone with his wife instead.

As shocked as she is to be called the c-word by Lutz, Liz is more horrified to realize he may be right. Meanwhile, Jack brings Tracy to a charity golf event to get closer to the chairman, however his plan backfires when Tracy acts too much like his uncensored self.

Jack sees an opportunity for budget cuts when Josh's contract is up, forcing Liz to go out of her way to motivate Josh into staying with TGS and not moving on to a rival show. Meanwhile, Kenneth earns a coveted spot in Tracy's entourage and Jenna gets in trouble over a misquote in Maxim.

Jack forces Tracy to host the Source Awards. Meanwhile, Liz goes to great lengths to prove to her African-American date that she's not racist.

Jack helps his brother Eddie land a job at TGS, Liz is forced to make desperate staff cutbacks, and Tracy seeks spiritual fulfillment with help from Kenneth.

Jack and Kenneth work together when Jack discovers that another NBC executive is after his job. Meanwhile, Pete and Liz adjust to life as roommates, and Tracy learns he's a descendant of Thomas Jefferson.

While Liz is finally in a happy relationship with Floyd, Jack is desperately trying to hold on to his job after his fireworks fiasco aired on television.

Tired of New York City life, Floyd plans a move to the Midwest and asks Liz to consider going with him. Meanwhile, Jack takes a trip to Paris out of which he returns engaged, and Tracy works on financing his latest career move.

Liz struggles to maintain her long-distance relationship with Floyd and must also use Kenneth's help in finding a missing Tracy. Meanwhile, Jack's marriage situation with Phoebe causes his mother to stop by.