After Liz decides to put out more positive energy to help her dating life, she receives a message from her ex, Floyd--he is back in town. She returns his call and he tells her he's in New York and wants to meet up with her the next night.
Danny falls victim to one of Frank, Toofer, and Lutz's pranks and Jack wants to team up to get revenge. Jack points out that the writers are jealous of Danny having it all, but now it's time to exact his revenge and Jack will help him with his plan.
Liz discovers that Floyd is in New York with his fiancée Caitlin, and they are competing for a dream wedding on "The Today Show." Liz is heartbroken, especially when she can hear the actual show with Floyd being taped outside her office.
Danny's plan is set in motion when the writers believe a toxic gas is filling the building and the men are ordered to undress in order to save their lives. As soon Toofer, Frank, and Lutz get down to their underwear, Jack brings in the TGS dancers to take photos.
Liz meets Floyd for dinner and tells him she knows about his engagement and "The Today Show" dream wedding. He apologizes that Liz had to find out about his engagement on TV and asks her if she's seeing anybody. She immediately changes the subject.
Ever since Jenna and Tracy were forced to listen to 12 hours of Kenneth sharing his childhood stories, they've been having graphic sex dreams about him. Now Jenna and Tracy are too scared to fall asleep because they have no idea what kind of sick dream of Kenneth they will have next. It's time to "Elm Street" the problem and kill Kenneth in their dreams.
Floyd begins to act loopy at the restaurant and Liz suspects the recovering alcoholic is drinking again. She discovers he's been drinking the glaze on his salmon entrée, which is made of Jack Daniels whiskey. Liz tries to get Floyd back to the hotel to sober up. But, an angry Floyd accuses Liz of trying to ruin his wedding and she leaves, hurt.
The writers discover that Jack belongs to the secret college society "Twig and Plums," and find out about the rule that every time somebody says the name in Jack's presence, he has to leave the room. After being embarrassed one too many times by the writers saying "Twig and Plumbs" in a crowded room of Jack's colleagues, he exacts another form of revenge: threatening to sleep with Frank's mom. The writers back down.
The next morning, Jack shows Liz a taping of "The Today Show" with a very drunk Floyd pestering the hosts. As an apology, Liz gives Caitlin free "TGS" mouse pads and a "Dateline" wallet. Caitlin accepts Liz's apology. Liz tells both Caitlin and Floyd to be happy. Liz goes so far as to agree to give a reading at Floyd and Caitlin's upcoming nuptials.