Elsewhere, "James" wraps up another date. Jenna starts to head upstairs, but Franco sweeps her up for a passionate kiss. Jenna swoons and leans in for more, only to be disheartened when Franco says he only did it because he thought there was a paparazzo nearby. He tells her to swing by his apartment at dawn so she can get caught leaving his house in a shirt and a look like she "just got drilled."
Back in Massachusetts, Jack finds more signs that Nancy and her husband are on the express train to Splitsville. He returns to the living room to find Kenneth disturbed that typing "Nancy's secrets" into the Internet only results in a website for a store that sells wig extensions. Jack begins to think aloud about everything he's seen there and what it means for Nancy's marriage. He points out that Nancy's high level of organization (which he first witnessed in high school German class) reveals that she and her husband are actually vacationing in two separate places. Kenneth tells Jack he has to stop with these "what ifs." He tries to click out of the calendar but only manages to take a picture of both of them. Lithe he may be. Techno-savvy, not so much.
Back on the UWS, Lemon finds Randy with tell-tale signs that he went out last night after she fell asleep, specifically the word "SLUT" written on his forehead. She tells him that he's sown his wild oats enough. It's time for him to ship back home. He says he won't go home until he gives her a makeover. She gets all excited. Then he locks her in the closet -- fitting -- and heads out for another big gay day.
In Massachusetts, Kenneth grows increasingly agitated, so Jack reveals that he saw the voicemail code on Nancy's phone hours ago. He is finally ready to listen to his message. In the message, Jack confesses that his love for Greta (Nancy) has lasted since high school German class, which he took just to be with her. He recites German poetry to her. Aside from the topless chicks in the hot tub, who interrupt the message, it's quite romantic. Upon hearing it sober, Jack has a moral crisis and doesn't want to erase the message. But Kenneth sets him straight and tells him that Nancy would have contacted him if she wanted him in her life. Jack hems and haws, so Kenneth takes the liberty of erasing the message. Jack decides Kenneth is right, and they leave -- Kenneth through the doggy door. Kenneth takes his pants off in preparation.
The next morning, Lemon walks into the writers' room to find the staff playing a shot game to the Today Show -- every time they give a dumb travel tip, drink! Jenna, in a man's shirt and no pants, interrupts the game to seek Lemon's guidance about her fauxmance with Franco. Since the kiss, everything seems hollow. Lemon tells her what she's feeling is perfectly natural, and that she wants something real. Lemon's pep talk is interrupted when she spots Randy and his sailor boyfriend on the Today Show, announcing their dishonorable discharge from the Navy, spur-of-the-moment engagement, and elopement to Massachusetts. Lauer tells them to save money by taking a sandwich. Drink!