Lemon has the winter blues and decides TGS needs to go on a road trip. She suggests Miami, but Jack opts for Boston, since he's jonesing to visit Nancy Donovan. Things take a miserable turn for the cast and crew, who have to contend with bullying Bruin Beat writers. Meanwhile, Tracy sets about offending everyone possible, in this instance historical re-enactors-slash-tour guides. The relocation even makes Kenneth surly. The staffers revolt, so Lemon tries to turn their rage into a "Screw you, our show is awesome!" edition of TGS to stick it to Dale Snitterman, some cost-cutting middle executive that Lemon in fact made up. Except it all goes pear-shaped when Lemon realizes she didn't make up the name but in fact saw it in the building. The gang descends upon the Bostonian and expose him to a terrorizing rendition of the Truffle Shuffle, courtesy of Lutz.
Meanwhile, Nancy tells Jack that her husband has left to rebuild Brad Pitt's shoddy houses in New Orleans. She interprets this as a thinly veiled attempt on his part to force her to ask for a divorce. She tells Jack she'd go through with it if only she could sell her house and gets some money. Jack orchestrates his own thinly veiled conspiracy and sends Kenneth (with bangs on a different side!) and Cerie to make an offer with his money. The reality of potential independence scares Nancy to "La la la!"-ing with her hands over her ears. Jack finally coaxes the taciturn Bostonian to admit they have feelings for each other and get going on her divorce. Could there be a Valentine's wedding for Jack and Nancy?
Lemon enters 30 Rock in a huff: "Ugh, I hate January! It's dark and freezing and everyone's wearing bulky coats. You can do some serious subway flirting before you realize the guy is homeless." She's had only online Boggle to keep herself entertained. Likewise, the whole staff is cranky because of their SAD-ness. Jack gets a text from Nancy Donovan, who proves that even the Female Larry Byrd gets more play than Lemon. Lemon asks how things are going with Nancy. Jack says they're just friends, even though he has elaborate fantasies of her husband Mark dying in a boat explosion. He says they haven't discussed a possible divorce yet, since it's not really a text-message type of conversation. Lemon gets off on the show's floor and passes Kenneth who is, perhaps, 1% less chipper than usual. He stops just past her and apologizes for his gruff manor, says he's got "winter madness." Meanwhile in the writers' room, Lemon finds the staff in chaos after Lutz chose Subway for the staff lunch. Guess they're not fans of honey oat. Credits.
Jack's office. He gets an incoming call on his phone from Nancy. The sound appears to cut in and out, prompting Jack to slam Jonathan for not being a stereotypical tech-savvy Indian. Nancy says she's just screwing with Jack, so he pays her back by saying, "Oh, very funny Donova--" and freezing in place. She thinks the computer froze. Everyone has a good laugh. Except Jonathan, the berated minority, who is summarily dismissed. Nancy tells Jack she's coming down to New York in five months, but maybe he could come to Boston in the meanwhile. His only compelling reason is a Harvard B-School reunion that's the same weekend she's coming down to New York. Disheartened, Nancy says she has to go.
Downstairs, Pete tells Lemon he's got an idea to boost staff morale: Miami road trip! Lemon doesn't know if it's fiscally feasible, but is too tempted by the idea of getting her old lady on to pass it up. They take the proposal ("MIAMI = SYNERGY") up to Jack's office and strings together some corporate mumbo jumbo. He greenlights it immediately, not because he actually wants them to take the show on the road, but because he wants an excuse to visit Boston. He tells them to re-route the trip... to somewhere even more wintry than New York.
Downstairs, Lemon tries to get the group excited about their impending road trip, but once they learn it's not Miami, they're over it immediately. Frank objects to the bars closing at 2:00 a.m. Jenna doesn't like that it's even colder than New York. Toofer, on the other hand, relishes the chance to mention that he went to college near Boston (at Harvard). Pete bursts their bubble even further by telling them they'll have to cut costs by doubling up on rooms in the hotel and taking the bus there. He also warns the gentleman that there will be no on-demand films or internet in the hotel, so they should plan ahead porn-wise. Big groan from the nearly all-male staff.