Maya and Finch attend designer Oscar Milos's fashion show using Nina's tickets. At the party, a drunken Maya makes some caustic remarks to a newspaper reporter, resulting in Milos pulling $3 million worth of advertising from the magazine. Maya decides to try and get the advertising back herself, without help. Meanwhile, Jack helps Elliott with his new girlfriend. Jack sends Elliott's date poems, flowers and much more in Elliott's name. She ends up dumping Elliott because ""he"" was smothering her.

Finch sneaks a look at the office Christmas presents and is disappointed by his when he discovers that it's not what he wanted. So, he sabotages the office Christmas. Meanwhile, Nina learns the true meaning of casual wear, Elliott protests the commercialization of the holiday and Maya rags Jack about his selfishness.

Maya and Jack accidentally kill Finch's cat but feel pretty guilty when he has it stuffed and sits it on his desk. Nina's advice to some Nature Scouts causes Elliott's mother to leave her husband.

Jack worries over what to get Donald Trump for his birthday; the two share the same one and Trump always gets him a better gift. Finch breaks the ""assistant's code"" when Jack presses him for information on the gift. Meanwhile, Maya and Elliott search for a couple who shares their interests. The couple they meet, however, misinterprets their offer to go swing dancing.