Jack goes shopping for an engagement ring, for Elisa, with Liz. Elisa tells Liz a secret, and a prank results in an injury back at TGS.

Liz and Pete try to rig the audition process; Tracy and Jenna decide they should conduct their own search for the next 'TGS' star.

Liz searches for a man she met in her dentist's waiting room. Jack fears for the future when he learns a cable company may have its sights on NBC. Jenna helps Tracy try to get a Tony award.

Liz uses her newfound confidence to solve Pete's problem with a difficult editor (Paul Giamatti); Jack tries to cheat mortality; Tracy vows to be present when his wife gives birth.

As Jack tries to cozy up to the owner of Kabletown, Liz fakes being pregnant to help Avery gain advantage over a competitive colleague. Elsewhere, Tracy and Jenna clash when trying to share a gift from their new bosses.

With their show targeted for cancellation, the "TGS" crew desperately scramble to mount a top-notch production for their 100th episode. Meanwhile, Jack reconsiders a vital decision in his life, and Jenna mulls over motherhood.

Realizing that Jenna could decide the Presidential election, Liz and Jack stage a debate to win her support and her followers. Kenneth turns to Tracy for advice on how to be an informed voter, while Pete tries to recreate the magic of the 2008 election.