Wedding fever hits TGS, leaving Liz to sort out Grizz's dilemma when both Tracy and Dot Com want to be his best man. Jenna's new boyfriend, Paul, raises Liz and Pete's suspicions, while Jack is finally forced to deal with the death of his mentor, Don Geiss, when Geiss leaves him a strange but meaningful inheritance.

Liz questions fate when she meets the man of her dreams, while Jack's love triangle between high school love, Nancy Donovan, and CNBC anchor, Avery Jessup, comes to a head. Meanwhile, Jenna's boyfriend is confronted with a similar dilemma when his desire for another woman threatens to ruin their relationship, and Kenneth, with the help of Tracy, tries to avoid a promotion that would land him in LA.

Jack recommends that Liz start seeing a therapist when she worries that Carol is getting bored with their relationship. In an attempt to take Jack's advice, Liz begins talking to Kenneth about her problems. Jack also finds himself caught up in one of Tracy's schemes when Tracy tries to convince him to invest in his son's theme restaurant in Times Square. Meanwhile, Jenna and Paul celebrate their six month anniversary.

Liz and Avery try to persuade Jack to disclose two secrets he's been hiding from his mother, who visits for the holidays. Then, Liz tries to repair Jenna's relationship with Paul; and Tracy tries to block his film's release because it undermines his newly invented serious persona.

Chaos builds when bigwig Hank Hooper marks "TGS" for cancellation, yet Jack persuades him to let the staffers stage the show's 100th episode.

The "TGS" crew anticipate their summer vacation. Liz lands in the Hamptons for some rest and relaxation, but she gets the summertime blues when Tracy moves in next door. Elsewhere, a lonely Jack latches onto Kenneth for company; and Jenna's new job impacts her relationship with Paul.

Fed up with New York City after being mugged, Jack sets out to protect the safety of the city's elite by announcing his run for mayor. Meanwhile, Liz revels in sacrificing the good of the city to look out for her own interests, and Jenna and Paul are thrilled by the perversion of acting like a normal couple.

Jack's mom upstages his ribbon-cutting ceremony. Meanwhile Jenna hooks up with a "rock star" and Tracy frets about his son heading to college.

Jack sets Liz up on a blind date to show her what she's missing in her relationship with Criss. Meanwhile at KableTown, Jack has to scramble when his plan to manufacture couches hits a speed bump. With Tracy's help, Jenna orchestrates a public meltdown to get Paul's attention.

Kabletown chooses to stop funding live shows for TGS. While Liz and Jack embrace the change, Kenneth argues that live format should be kept intact, and he tries to convince the TGS staff to fight for their right to be live by taking them and our audience through a magical look back at the illustrious history of Studio 6H.

The episode was filmed twice. The East Coast version aired for the Eastern, Central and Mountain time zones. The West Coast version was aired in the western, Alaskan and Hawaiian time zones.

Jenna annoys Liz with her wedding envy, Jack devises a plan to avoid disappointing his visiting mother and Tracy attempts to cheer up Kenneth.