In searching for tuxedo shoes for her disastrous date Wesley (returning guest star Michael Sheen) in preparation for Cerie's wedding, Liz Lemon found another potential soulmate - this time, in the form of the dashing pilot Carol (played by the consummate Matt Damon).
As she confesses her faith in Carol as her one true lover to Wesley in order to end their tenuous relationship for good, Liz reveals a couple of less than satisfactory secrets about herself. In overhearing this, Carol is shocked and leaves at first, but returns to find Liz at the set of TGS (where Grizz and Feyonce's wedding is taking place) and offers to give their relationship a shot.
Meanwhile, Jack Donaghy assuages Nancy Donovan's (guest star Julianne Moore) tempers by telling her that he wants to be with her. This relationship is suddenly shattered, however, by the revelation that Jack impregnated his other paramour, Avery Jessup (guest star Elizabeth Banks). Nancy breaks up with Jack and he subsequently proposes to marry Avery, to which she accepts.
Jenna Maroney is not without some romantic adversity of her own, however: she is insulted upon discovering that her lover Paul (guest star Will Forte) is impersonating musician Cher behind her back. In an attempt to balance the love he shares for both women, Paul attends Grizz and Feyonce's wedding dressed up literally as half Jenna and half Cher. Flattered, Jenna accepts his compromise.
Away from the tangled romantic scene and distraught with the idea of having to move to California to resume his page duties, Kenneth seeks the counsel of none other than Tracy Jordan. Tracy's destructive advice - to do as bad a job as possible - winds up in Kenneth's hands at the worst possible time as Kenneth blunders his way through a tour with the high ranking Kabletown executives. Tracy's plan works, but not in the way Kenneth hopes - Pete Hornberger is forced to let Kenneth go, and Kenneth responds by unleashing a politely drunken tirade in the middle of Grizz and Feyonce's wedding devoid of expletives and filled with hateful-sounding praises, in typical Kenneth fashion.
Jenna is infuriated with the discovery that her boyfriend, Paul, is impersonating Cher behind her back, and she shouts:
"Oh, spare me your lame excuses. Maybe I'm old-fashioned, but when a girl dates a straight man who impersonates her on stage for mostly gay audiences, she has certain expectations. Fidelity, Paul! It's not just the name of a bank that sued me!"
Worried about the impending transfer to the Los Angeles division of NBC, Kenneth pleads Tracy for advice, to which the wise Tracy responds:
"Do a sloppy job and they'll leave you alone! That's how I got out of foreplay with Angie... and my taxes."
On meeting Jenna's boyfriend, Paul, at Cerie's wedding, Jack strikes up a conversation. Paul, having relationship troubles of his own, asks Jack:
"Do you think it's possible to love two women at once?"
To which Jack woefully responds:
"I know it's possible, but at some point, you have to choose, Paul. You can't delude yourself with thoughts like 'what if I could somehow combine them into one perfect woman, like a s'more you can take a shower with?'"
In a conversation with Carol, Jack Donaghy brings up the pilot behind the Hudson River miracle, "Sully" Sullenberger, and Carol dismisses him:
"You know what a great pilot would have done? Not hit the birds. That's what I do every day, not hit birds. Where's my ticket to the Grammys?"
Kenneth, out of his depth, is trying diligently to be as awful a tour guide as he possibly can, and the ploy is working pretty well:
"Good afternoon, and welcome, NOT! We begin our tour of this once great network outside studio 6H. What? Uh-oh, ring ring!"
After feigning the ringtone, Kenneth holds up his phone to his ear and begins a 'conversation':
"Wassup? Nothing, just giving a tour to a bunch of uggos. Anyway, let's meet up later and smoke some drug cigarettes!"