Lemon constantly has her hands full, juggling corporate interference from Donaghy and off-the-handle star antics from Jordan, all while attempting to salvage her own personal life.
Liz tries to stop the TGS staff from ruining her chances at adoption when an adoption agency evaluator comes to 30 Rock to see if she would make a good mother. Jack returns from Washington D.C. and starts his job again at GE, only to discover he has been demoted. Jack tries to get his old job and office back from Devon Banks and Kathy Geiss. A feud between Tracy and Jenna wreaks havoc among the TGS staff. Megan Mullally and Will Arnett guest star.
To get out of jury duty, Liz flies to Chicago only to be sat next to Oprah Winfrey on her return flight to New York. An argument between Tracy and Jenna leads to a "social experiment" to prove who is right. Kenneth challenges Jack's morality after an "Olympics snafu".
Liz's former roommate from Chicago, Claire Harper, comes to visit her and Jenna. She develops a stalker-like obsession with Jack. Kenneth is unhappy with the new page uniforms so Tracy decides to cheer him up with the help of Night Court cast members Harry Anderson, Markie Post and Charlie Robinson. Jennifer Aniston also guest stars.
Jack and Liz get stuck in a snowstorm while going to Liz's 20 year high school reunion at White Haven High in Philadelphia. Liz tells Jack she was a big nerd in high school, but flashback scenes reveal that she was actually always hurting people's feelings. Leighton Meester and Blake Lively were originally going to guest star in this episode until their scenes were cut before the episodes broadcast. Steve Martin and SVU's Diane Neal will guest star in this episode.
Liz fights the idea of going to her high school reunion while Jack deals with bad news.
Jack keeps the entire Girlie Show staff at work to have a live Christmas Eve Special, just to avoid being home with mother.
Jack grows close to his mother's nurse.
While the flu spreads quickly amongst the TGS cast and crew, Jack is selective about who receives vaccinations from Dr. Spaceman.
Jack ropes Liz into accompanying him on a business retreat.
Liz tries to begin a relationship with a new tenant after accidentally receiving his mail. Meanwhile, Jack's appearance causes Elisa's grandmother to disapprove of the relationship, and Tracy has trouble maintaining the lifestyles of Wall Street frat boys.
Not realizing it's going to be the ultimate lovers holiday, Liz insists her and Drew have their first official date on Valentine's Day; while Jack prepares himself for an unconventional Valentine's Day spent at church with girlfriend Elisa.
New York spirals into chaos after Tracy appears on Larry King Live, while Jack considers taking his relationship to Elisa to the next level.
Liz befriends a pregnant teenage donut shop employee, in an attempt to adopt her baby. Back on set, Jenna vies for more attention from the TGS staff as her birthday approaches.
What was going to start out as Liz's new beginning has now turned into her worst day ever. She gets hit by a bike messenger, called for jury duty, and now has to defend Tracy and Jenna's inappropriate behavior from the televised St. Patrick's Day parade.
Liz comes back from her lunch break with Drew. Jack notices her takeout bag from one of New York's hottest restaurants, Plunder. Liz says it's amazing on how many advantages Drew gets for being good looking. From being stopped on the street by Calvin Klein and offered a modeling gig to getting out of parking tickets. Jack tells her Drew is living life in a bubble only reserved for good-looking people.
Liz and Jack are busy dealing with Tracy's latest stunt: wanting to be sent into space.
TGS just got done filming their 50th show and Liz and the writers are ready to celebrate.
Liz is having a hard time with her short-term suspension, since being accused of sexual harassment at the workplace.
Before Jack can propose to Elisa, he turns to Tracy for insight on the stresses of married life.
Jack's mother, Colleen, is in town and Liz is surprised to not find Jack in a rancid mood because of it.
Liz tries to encourage Jack to find his real father, but Jack wants nothing to do with it.
Jack begins to bond with his real father. Meanwhile, people start seeking Liz out as a relationship expert, and Kenneth helps Tracy deal with past embarrassments.