Jenna tries to help a lovelorn Liz rebound from a broken relationship. Elsewhere, sleep deprivation impacts new father Jack, who begins to lose his business savvy and negotiating prowess; and Pete and Frank form a rock band.

Liz tries to turn her personal life from drab to fab by revamping her dream apartment. Meanwhile, Avery is held hostage, and Tracy discovers that Kenneth, Dot Com and Grizz have forged a solid bond while he was away.

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.

Jack learns to appreciate Leap Day while Tracy takes the writers to a restaurant to spend an almost-expired gift card. Liz helps Jenna seduce an internet billionaire.