The episode starts out by introducing us to 4 new interns at 30 Rock, all former investment bankers hired by Jack after they lost their jobs on Wall street. They are all dressed in crisp business suits and eager to work, but as Jack himself says, they have absolutely zero real-world skills. They all tear off at full speed as he sends them on and errand to get flowers, bath soaps and Spanish magazines for Elisa's grandmother, who is arriving soon for a visit to New York. Jack has met her once before and got the impression that she did not like him, so he really wants to win her over this time. He gives her the presents and takes her and Elisa on a tour of NBC (the special tour where guests get to see Conan without his wig!), but she still hates him, and Elisa cant understand why.....until they all see the villain of her Spanish-language soap opera. He is known on the show as "El Generalissimo" and he is pure evil- and looks remarkably like Jack (plus one very cheesy moustache).
Liz comes to work with a handful of mail that was delivered to her erroneously, marked for apartment 13B, and not her apartment, 3B. She runs into Jenna in the break room and Jenna investigates (ie opens) the mail and discovers that the intended recipient is a recently divorced male doctor who likes Muppet movies, golf, and baking delicious desserts (guest star Jon Hamm). Further misdirected mail arrives and Liz discovers that her new neighbour also is heavily involved in charity work and trains seeing-eye dogs (presumably in his spare time?). Knowing all that she does about him, Liz is becoming quite intrigued about meeting this Dr. Andrew Baird . After work, she returns the mail to him at his apartment and is immediately smitten when she finds him charming, handsome, and in the middle of making his own cake frosting.
The interns meet Tracy and immediately invite him to come out after work with them. Tracy feels he needs to go to keep his reputation as a young and wild comic alive, so he just as eagerly agrees to join them. After a few nights of hard partying, however, he realizes that he simply cannot keep up with the 4 hard- partying 20-somethings. Rather than telling them that he is getting too old to stay out all night, he decides to use his financial resources to re-open the bank that had formerly employed them so that they would all be too busy again with work to ask him to go out anymore.
Jack becomes so obsessed with turning Elisa's grandma's opinion of him around that he buys the Spanish-language soap opera she watches and enlists Liz to write a script in which "El Generalissimo" is killed off. She does and Jack is sure his problems with grandma are solved. The only hitch is that the actor who plays him (Alec Baldwin moonlighting as the fictitious Hector Moreda) doesn't want to lose his cushy job and refuses to die as scripted. Jack goes to meet him and they eventually work out a deal in which "El Generalissimo" will change and become adorable to aged Puerto Rican women so that Elise's grandmother will fall for him and therefore warm to Jack.
As the real Generalissimo is cleaning up his act, Liz is tapping into her own inner-generalissimo and doing more and more morally questionable things to win the affections of Dr. Baird. She opens his mail (which she originally chastised Jenna for), wears a t-shirt from one of his charity causes (which she has never supported) as she knocks on his door to enlist his help to find her lost dog (which she doesn't have), and then invites him to a "welcome to the building party" (which she has no intention of actually holding). When an unsuspecting Drew shows up to her party, she tells him he is a day early but invites him in anyways (all part of her cunning plan). Through a series of comic misadventures, including the touching/bizarre return of her non-existent dog, he ends up lying prone on the floor, drugged and terrified that Liz has evil intentions towards him.
A few days later Dr. Baird gets some of Liz Lemon's mail and takes it to her apartment. He tells her that he opened it (turnabout being fair-play), and based on what he has learned about her, he would have been interested in meeting her without her needing to resort to all of her treachery. They decide to start over from scratch and schedule a date. Meanwhile, Jack and Moreda's scheme has worked to perfection and now Elisa's grandma loves Jack like a son. Just to make sure it stays that way, though, Jack has Matt Lauer end each NBC Nightly news cast with Tito Puente music playing over images of adorable Latino children.