Up All Night
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.
Black Tie
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.
The Head and the Hair
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, but cerebral Liz finds it strange that she's more interested in the attractive one. Meanwhile, Kenneth and Jack switch roles.
The Rural Juror
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.
The Baby Show
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."
The Break-Up
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.
Tracy Does Conan
Jack bumps Jenna's scheduled appearance on 'Late Night with Conan O'Brien' by booking new star Tracy. Jenna, still irate over watching the 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.
Jack Meets Dennis
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 Liz Taylor.
Jack-Tor
After being pressured by Jack to plug GE products into her show, Liz integrates Jack 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.
Jack the Writer
Liz struggles to keep Jack out of the writers' room and Kenneth soon learns that working for Tracy may be more than he expected.