Jack chats up the new couple. "Where did you two meet, Amber alert?" he needles Lemon after Tender Meat 'N' Coffee goes to the bar in hopes of being served. Jack congratulates her on achieving the status that dating a younger person brings. He wants her to have fun. "I have fun. I went up on my roof the other day," Lemon retorts. Jack sets the ground rules of a May-December: buy them a few gifts, never give out a home phone number, and set a curfew.
The next day Cerie bumps into Lemon in the hall, questioning whether or not she had actually seen her at Marquis last night. The answer: yes. Cerie wonders if Lemon slipped out of bed and wandered mistakenly into what twentysomethings do -- the answer: no. Next, Jenna struts in on the arm of a kid who looks like Superbad. "Guess you aren't the only Cougar in town, huh Liz?" then she and her pre-teen bicker about whether or not he can have a soda. Later, when Tender Meat comes by with coffee, Lemon plays by Jack's rules by declining his invitation for an impromptu lunch and then giving him a video game. In walks Frank with a painting called "One-Armed Mermaid."
Lemon picks up Tender Meat at his place and is going to spring for a cab to his delight. As they stand in front the mirror, he observes, "We look awesome together...alright mom, I'm taking off." Liz Lemon's brain alarm sounds off in much the same way it did when she was dating her cousin. Then mom walks in. She's got auburn hair and black-rimmed glasses. Sound familiar? Her son puts her arm around her. Lemon: "Yep. That's what we look like. Shut it down."
The other plot thread begins with Tracy, who barges into Jack's office with his minority little league baseball team from Knuckle Beach, the toughest neighborhood in New York. Jack recollects fondly his own High School baseball team winning the Boston City championship against all odds because they were all-white and they had to play an all...anyway, they won, and Jack was then taught how to dream. He asks the kids their dreams and we get a neat Annie Hall homage where they speak to camera: "I'm going to do vending machine maintenance"; "I'm going to get shot by a cop and sue the city"; "I'm going to be a talkative doorman with a drinking problem." Tracy encourages it wholeheartedly, a la mentoring transvestite prostitutes, but Jack wants more. The winless kids require his inspiration.