On her way into work at Rockefeller Center, Liz catches Jack kissing a woman and sending her off in a car. Jack confesses he's been out all night with Zarina, a pizza heiress. Jack calls it a walk of shame, but Liz tells him to embrace it, make it a "stride of pride." Liz is happy to report she's had something of sexual awakening. Jack goes on to explain that the heiress is just one of several women he's seeing. Like the gang from "The Great Escape," each has a separate strength. When Liz asks what would happen if they should find out about each other, Jack explains that they're all adults - and that any sort of fracas might be intensely erotic.
At the TGS offices, Liz is making small talk with the staff when Frank bursts in with the latest issue of THEM magazine. It features an article on Jenna looking great at age 56. Liz puts the staff on high alert - they've got to ensure Jenna never sees the damning pictorial. A furious Jenna arrives - but it's not the article she's upset about. It's how Tracy has insulted Liz on Twitter. The tweet reads: "Women are not funny. Never have been. Never will be." Liz screams aloud and marches into Tracy's dressing room. She tells him he's insulted both Jenna and her. Tracy insists that Liz say something funny. Put on the spot, Liz can't quite deliver and storms off.
Pete dispatches Kenneth to steal the THEM magazine out of Jenna's dressing room before she can see it. But Jenna's there already, so Kenneth must improvise. He puts a series of awkward and overt romantic moves on Jenna, who's all too pleased to get the attention. As Jenna lusts after Kenneth's hairless shins, Kenneth secrets the magazine out of the room to Pete, waiting nearby.
We see a montage of Jack's romantic moments with his various partners: kissing in front of a painting in a museum with one, playing tennis with another, smoking cigars with a third. We see him strolling at night with yet another woman, Mindy, when Jack runs into Zarina. Jack breaks the unpleasant truth to her that he's not exclusive with her. Zarina just smiles and lets Jack know she's not monogamous either. Just then one of her other paramours shows up - Olympic swimmer Ryan Lochte. "Ryan is my sex idiot," she whispers to Jack. As Zarina and Jack are having a tense discussion, Ryan Lochte and Jack's bimbo Mindy begin to kiss. Zarina breaks it up, telling Lochte to focus up.
Jenna explains to Liz that she planted the article about being age 56 in the magazine. Her plan is to skip the middle-aged actress phase and go right to aging slut. If Helen Mirren can look hot, so can she. Jenna's in the running to be the spokesperson for Geri Chair, a mobility scooter for seniors. She threatens Liz that if she keeps pushing to make her seem young to the press, she will take her down.
Liz visits Jack in his office to complain about Tracy. But all Jack wants to do is convince Liz and himself that he's all right with being one of several men for Zarina. Still, he still can't quite understand why he's not seen as the complete package. He wonders aloud if he should meet the other men in Zarina's life. Liz is emphatic: bad idea.
Tracy makes an entrance into the studio, introducing his comedic monkey, Professor Wigglebottom. The crew gathers around, laughing and listening as Tracy rants about how monkeys in clothing are always funny, as are the Three Stooges and male nipples. He goes on to denigrate women as unfunny - and finally Liz has had enough. She announces to the staff that she and Jenna will be reprising their 1996 two-woman show in the studio that afternoon; attendance will be mandatory. When the staff applauds, Liz smiles - until she realizes they're actually clapping for the monkey.
Jack's thrilled to get a text from Zarina: "Thinking of you sweetie." But after considering it, he suspects it's part of a group mailing. He has Jonathan summon Cerie to explain how multiple recipient emails work. She confirms Jack's suspicions, exposing a handful of other recipients, including Ryan Lochte. Incensed, Jack insists that Cerie teach him how to respond to everyone on the list.
Liz gingerly approaches Jenna in her dressing room. Jenna's upset; it appears that Jamie Lee Curtis may have beaten her out again on a commercial, this time for the Geri Chair. Liz asks Jenna to perform their old show together, as a favor for women everywhere. Jenna considers it for several seconds and then, to Liz's surprise, agrees to do it as long as it includes the doctor sketch.
Jack's gathered all of Zarina's lovers in his office. He wants to discover what they have to offer that he does not. Jack sizes them all up: the African-American guy to upset her parents, the sex idiot for unbridled experimentation, the mean Wall Street type, a hippie and Ken Tremendous, he of magnificent hair. Jack wonders aloud where the father figure is until he realizes... it's him.
The staff assembled in the audience seats, and Liz announces the start of the show. It's "Maroney and Lemon," a Piven-nominated comedic tour de force. Liz dons a smock and vaults into a sketch about a little girl who's visiting a doctor in an attempt to be younger. The first joke lands successfully, and soon enough, the staff (including Tracy) is laughing and laughing. A comedic song summarizes the remainder of the sketch. The two performers take a bow as the audience gives them a standing ovation. Tracy approaches Liz to apologize. He tells Liz she was really quite funny - the whole idea of a lady doctor was a crackup. Liz is appalled, but she'll take it. Jenna receives some praise herself. In the audience was Gerald Chair, inventor of the Geri Chair. After watching Jenna perform as a little girl, he's convinced she really is old enough to be his spokesperson. Jenna's thrilled.
Later, Jenna sneaks into Jack's office to indulge her passion for flashing her breasts at the Empire State Building. She's surprised to find Jack still there. He's upset, fearful he's just too old to be the complete package for Zarina. But Jenna offers an alternative take. She tells Jack he should embrace being the older man, avoiding all the tedious club-hopping and other obligations of a younger boyfriend. Jack takes it under consideration.
We see Liz in her pajamas, blissfully writing at the end of the day. She recounts some of today's nuances of her sexual awakening and it causes her to wonder: is accepting who you are the secret to getting what you want? Do men and women see the world so differently? Can we get everything we need from one person?