Lemon worries that her relationship with Carol -- whose last name, we learn, is Burnet -- is reaching a holding pattern, so Jack advises her to see a therapist. Instead, she unloads all of her man neuroses on Kenneth. There are lots of flashbacks ranging from her disappointment with Santa Claus to how her uncle instilled in her a deep-seated gag reflex for eggs. The one-sided exchange quickly becomes emotionally unwieldy for Kenneth and his many emerging personalities. Jack takes on the burden of Kenneth's pig-related childhood traumas, himself dissolving into tears about latent daddy issues.
Along the way, Tracy asks Jack to invest in Staples, a theme restaurant fronted by his son Donald (who's two years older). Naturally the restaurant is a poorly conceived mess at which the main highlight is a fight show between unlicensed Japanese monsters with names like Godzila and Mecha-Godzila. (Yep, the one "l" is intentional, for legal reasons.) After visiting Staples, Jack advises Tracy to cut off 43-year-old Donald. Then he gets a good ol' fashioned head-screwin' from Kenneth and blesses Tracy to continue throwing good money after bad, re: Donald's utterly unrealistic, highly unprofitable dreams.
It's Jenna and 'Gina's six-month anniversary, so naturally Jenna expects a proposal... to make a sex tape. Instead, 'Gina takes her to the vacant lot where they first "face-kissed" and asks her to come to Ohio to meet his parents. Jenna flips out, and Lemon warns her that self-sabotage is imminent. Jenna does not heed her advice and suggests the sex tape. 'Gina tells her (s)he can't live up to her adventurous expectations and breaks things off, leaving Jenna to evenly divide their panties and cry herself to sleep.
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30 Rock. Tracy barges into Jack's office screaming, "Hey! What's that sound? It was opportunity knocking!" Jack points out that Tracy didn't, in fact, knock. At which point, Tracy's two-years-older "son" (a.k.a. con man leech) Donald knocks on the door and walks in wearing a T-shirt that says "OPPORTUNITY." In hindsight, Tracy admits that Donald's initial plan to enter first may have more sensible after all. They want to try it again, but Jack tells them to get to the point. Tracy reintroduces Donald and lets his "son" make the pitch. Donald tells Jack he has the chance to get in on the ground floor of an exciting new business venture -- a theme restaurant Donald is opening in Times Square. Donald tells him they already have a sizable investment from Brown & Folderson. Jack tells the dim-witted duo that he never invests in anything without doing his research. He tells them he'll visit the restaurant tonight. Donald warns him that it'll be his loss if some other investor comes along first. Then, despite his phone not ringing, he takes a "call" from a "Mexican billionaire" named Señor Mexico and stars speaking in broken Spanish as he leaves the room. Of course Tracy runs screaming after him, claiming that Donald always leaves him out of the loop. Credits.
Downstairs, Lemon walks into Jenna's dressing room and starts talking to the back of Jenna's head. When "Jenna" turns out around, Lemon is startled to find that it's actually 'Gina (a.k.a. Paul, Jenna's drag queen impersonator-slash-boyfriend). Jenna explains that they're mirroring until they achieve touchless orgasm. Luckily for Lemon (or unluckily, depending on how you look at it), Paul declares himself "finished" just a second later. Then he takes off for work, and Jenna spills that they're celebrating their six-month anniversary that night. She thinks Paul is going to pop the question. Lemon says maybe it's a bit soon, but Jenna clarifies that she will say yes... to a sex tape. She says marriage is like death and that you lose all the spark. Lemon thinks the comfort and routine is the whole point of being with someone for a long time. Whereas Jenna thinks relationships are like sharks, Lemon says she and Carol (who haven't spoken in five days) are "legless turtles rotting on the beach." Jenna grimaces and Lemon realizes what an unflattering comparison she just made.
Newly insecure, Lemon heads up to Jack's office to ask him what makes guys bored in a relationship. "That's an excellent question," he replies. "The answer is, questions like that." She mentions that she's gone several days without speaking to Carol and has other issues that are building up inside of her. Jack advises her to find a therapist so she can unload her problems and move on with her "life" (air quotes his). She says she's tried but can't find anyone she likes. She asks if he's ever seen a shrink. Of course he hasn't, but he thinks it will be useful to her -- and even more useful to him, since he usually doesn't speak to a woman about these kinds of issues unless she's having sex with him.