Liz and Jenna work on their dating game when they're beguiled by two very different MSNBC staffers: a brainy geek and a brawny hunk, but cerebral Liz finds it strange that she's more interested in the attractive one. Meanwhile, Kenneth and Jack switch roles.

As part of his community service, Tracy must coach a little league team. All goes well until Jack takes interest in the team and turmoil starts from there. Meanwhile, Liz is asked out on a date by Jamie, the new coffee boy, who thinks Liz is actually younger than she truly is.

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.

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.