Jack and Kenneth try to erase an embarrassing drunk phone message he left on New Year's day, Jenna agrees to "date" James Franco for publicity, Liz's gay cousin comes to New York to visit, and Tracy thinks his wife's pregnant with a girl.
Liz proposes a TGS episode to be done on location in Miami in the dead of winter to boost morale, but Jack changes the locale to Boston so that he can be close to Nancy, whom he learns is about to get a divorce.
Liz Lemon takes Frank in as a roommate, and is pleasantly surprised when the two make a pact to help each other kick their bad habits. Meanwhile, Jenna Maroney turns to Jack Donaghy for help with her mother, Verna, who has come to visit.
Liz can't get anyone to give her a ride home from her oral surgery, which is scheduled for Valentine's Day. Meanwhile, Jack goes out on a date with a sexy, smart journalist, and Jenna discovers that her stalker has moved on.
Jack tries to find out why he's out the loop on a potential sale of NBC and why Don Geiss can't be found. Meanwhile, Liz looks for her "future husband," whom she met during a root canal, and Tracy launches his plan to win a Tony Award.
Jack tries to save his career by getting tight with NBC's new owners, Liz cannot escape running into her "future husband" everywhere she goes, and Tracy "comes clean" about remaining faithful to his wife all these years.
Liz becomes upset when her ex-boyfriend Floyd returns to New York to try and get married on the Today Show, Jenna and Tracy begin having erotic dreams about Kenneth, and Jack and Danny start a prank war with the writers.
While Liz goes to singles events searching for love, Jack tries to juggle his two relationships "Three's Company" style. Meanwhile, Toofer quits his job when he discovers that he's just a product of Affirmative Action.
Liz discovers that the TGS staff has been excluding her from their weekly hangouts, and strives to prove that she can be fun. Jack must choose between janitors and the shift time they both want, and Kenneth aids Tracy Jordan in being a good husband.
It's time for the Mother's Day special at TGS, and Jack's mom begins meddling in his two relationships, Liz's mom reveals her surprise true love, Tracy clashes with his pretend TV mom, and Jenna's mom is there because Jack's paying her.
Jack's relationship-juggling becomes more complicated when Nancy makes an unexpected visit, Liz reluctantly selects Wesley as her date to a wedding, and Tracy considers taking a role that could win him an Oscar.
Liz believes she's found her perfect man while between weddings with Wesley, Jack has to make a decision after Nancy meets Avery, Kenneth gets fired while trying to avoid a promotion, and Jenna's boyfriend becomes a Cher impersonator.
As season five of TGS begins, Liz and Carol are forced to confront their relationship, Jack and Avery battle over home decorating, Jenna becomes a TGS producer, and Tracy struggles with life at 30 Rock without Kenneth.
Liz finds out that a guy in editing is spreading rumors about her, Jack begins recording advice videos for his unborn son, Tracy takes steps to make sure he's there for his daughter's birth, and Kenneth tries to prove he has a purpose.
Jack's 24-hour "perfect game" of solving problems is put on the line when Liz needs relationship help and Tracy needs to learn his line for a commercial. Meanwhile, Jenna, Kenneth and Kelsey Grammer pull a con on Carvel.
Avery asks Jack to act as a mentor to someone besides Liz, but Liz has her own problems when her married 80-year-old father visits to cruise singles bars. Meanwhile, Jenna is mad because NBC has an obituary for Tracy but not for her.
Liz frequents a local boutique because she thinks she's helping the environment--and their jeans make her butt look good. Meanwhile, Jack helps an enemy's political rival, and Jenna helps Tracy aim for a Golden Globe nomination.
Liz suddenly becomes cool after she wins the crew lottery, Jack discovers that the microwave division has made the perfect microwave, and the writers play a prank on Pete after discovering that Jack's voice is used on a website.
Jack tries to help Tracy after he helps his "son" finance an ill-conceived theme restaurant, Liz turns to Kenneth as a relationship therapist, and Jenna thinks her boyfriend may pop an important question to her.
Jack tries to ambush his mother by inviting his father and Avery to Christmas dinner, Jenna misses her ex because they won't attend "New Queers Eve" together, and Tracy tries to maintain his new "serious" image.