When Tommy needs 2 million dollars, he calls on an old friend who is always ready to invest in Tommy's enterprises. Tommy asks Kristin to arrange accommodation and an escort for his friend's visit, a task she finds she can't bring herself to do. Tyrique is forced to switch from his bike to rollerblades when his courier job is threatened by the rollerblading Smoove. When Kristin refuses to arrange for the escort, Tommy makes the arrangements. When the escort ends up at the wrong hotel, as per Kristin's plan, Tommy gets Tyrique to take Kristin on his bike to send the escort to the right hotel, but Kristin sends her home and takes her place. Kristin takes Tommy's friend on a fun-filled night all over the city, much to his delight, and drops him off at his hotel before going home. The next day, Tommy gets his money and learns that Kristin took the escort's place. He's shocked, but Kristin isn't going to tell him what really happened.

Kristin is crushed when she overhears Santa and her two catty friends, Roz and Janis, mocking her behind her back. After she tells Tommy that desperately she wants their approval, he asks Santa to take Kristin out for a night on the town. On him. Santa grudgingly drags Miss Perfect along to a bar and grill, but the terrible trio make no attempt to hide the fact that they think Kristin is a bumpkin goody-two-shoes who will never fit in with their trash-talking ways. Kristin manages to win over Roz and Janis when she tells them a dirty sex joke, but Santa is not so easily sold. She decides to include Kristin for the girls' weekly visit at the massage parlor anyway and then clues Roz and Janis in on the real reason she brought her -- she's arranged to have their Swedish masseur, Thorr, give Kristin the "happy ending," just to see how far she's really willing to go to join the in-crowd. When Kristin freaks out during the massage, Thorr lets her know that Santa paid him to do it.

The tempestuous relationship between Aldo and his longtime girlfriend distresses Kristin, now that she's the object of his affection.

Kristin is ecstatic over landing the starring role in a play -- even if the play is off-off-off-off-off-off Broadway in some basement in Brooklyn. But, hey, a Manhattan debut is a Manhattan debut. Terry Bradshaw moves into one of Tommy's apartment buildings, and when his generous donation to Kristin's production becomes a one-upping contest between him and Tommy, Tommy puts away his wallet, and makes Terry write Kristin a check for the remainder of the $7000 she'll need to fund the show. Tommy and Aldo go down to the theater to see Kristin do her thing, but Tommy's apathetic compliment -- "Good job" -- makes Kristin think that he didn't like her work. So she confronts him, and he admits that he just wasn't buying her climactic kiss with the lead actor, what, since the play is called "A Kiss Before Midnight" and everything. When she asks why not, he says that the best acting comes from experience, and she clearly hasn't had much experience -- which reduces her to tears.

Kristin's down-home mother makes her first visit to the Big Apple to see her daughter. Despite Kristin's pleas to her co-workers to mind their language around her mom, since the woman's an even bigger goody-two-shoes than she is, Mrs. Yancey is greeted by a barrage of dirty talk from Tommy, Santa, Aldo and Tyrique. Kristin takes mommy to see her dumpy apartment, but the elder Yancey ruins the night by telling her that she and her father want her to come home, as she's been in New York for 2 1/2 years and still hasn't made it. Kristin goes crying to Tommy and Aldo, because she doesn't want to go home to Oklahoma and can't face the family and friends who thought she'd become a Broadway star. Tommy helps her out by setting it up so she can sing at The Cabaret Room, which ends up setting him back $53,000 and change. He takes out a full-page ad for her, and the event practically sells out, but Kristin's joy is short-lived when she overhears a waiter talking about how Tommy bought out the cl

Kristin and Aldo try to convince hard-hearted Tommy to fund the city zoo's Monkey Island, a haven for all the underprivileged simians in the neighborhood, but when he doesn't take to the idea, Kristin sends in the chimps to do the talking. Tommy's former business associate, Peter Medavoy, pays a visit to Ballantine Enterprises to see his old partner -- and takes Kristin by surprise with his confession that he just got out of prison for cheating the I.R.S. When Peter hears about her cause -- and that Tommy won't help out -- he turns over a new leaf, and tells Kristin that he knows some money men who can assist her in putting together a fundraiser. Tommy soon realizes that Peter's generosity is really just a ploy to get Kristin into bed, as he's known the guy a lot longer than she has. But since he has no credibility with Kristin, Tommy turns to Reverend Thornhill, and asks him to break them up. The Reverend quickly sizes up that the only reason Tommy's come to him is because he himself