Kristin copes with audition rejections and finds herself desperate to make ends meet, so she takes a job as the personal assistant to Tommy Ballantine, a high-powered real-estate developer. Talk about a mismatch. He's a slick womanizer known as "the master harasser disaster"; she's a virtuous naif. As it turns out, however, the playboy has met his match.

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

Tommy fights the planning commission for the right to put a 6-foot-tall neon "B" on the top of Ballantine Enterprises. When he finally gets permission, he learns from Aldo that the only reason the supervisor changed his mind was because Kristin sent the guy a cassette tape of his favorite singer, and asked that he repay her act of kindness by letting Tommy have his "B." Tommy goes to Kristin, wondering what she wants in return (because of course no one does favors for others without expecting something in return), but all Kristin wants is for him and Aldo to have dinner at her place, as thanks for giving her a job, so the guys join her for some down-home cookin' at her run-down, one-room apartment. After seeing the bad neighborhood she lives in, Tommy decides to repay her help by setting her up in one of his luxury model apartments -- worth $1.5 million -- free of charge. But she rejects his offer, as she needs more time to sleep on it.

Kristin mistakenly sends away Tommy's important client, after Tommy appoints her as his office gatekeeper.

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.

When Tommy convinces a famous architect to design his new building, he alienates Aldo by treating him like just an employee. Kristin tries her best to reunite them but they are both too stubborn to relent. Tommy gets invited to a party at the architect's house, while Aldo goes off to get the geologists report on the building site. Tommy finds himself in a delicate situation when he discovers the architect is gay and is attracted to him. Aldo arrives covered in mud to tell Tommy that the site is over an underground river. After an argument that is mis-interpreted as a lovers fight by the gay party guests, they reconcile and leave arm-in-arm.

Tommy gets hit on by supermodel Marinka at a fashion show. Kristin thinks the brochure for the apartments in Tommy's new building is "kinda blah," so she redesigns the cover. Tommy likes Kristin's design better than Santa's, and he asks her to redesign the rest of the brochure. Santa tells Kristin that she knows she's not as sweet and innocent as she pretends to be, accuses her of being after her job or something better, and tells her she doesn't know who she's dealing with. Tommy brings Marinka to the office, and she tells him she wants to have sex on his desk. Kristin gets stuck on a detail and needs Tommy's opinion. He tells her to call Santa. But when she does, Santa hangs up on her, and Kristin is forced to interrupt Tommy and Marinka, who then walks out on him. The next day, Tommy reprimands Santa, who cries and says she was looking after her sick mother. Tommy tells Kristin he thinks she should just stick to her job, as she obviously cannot handle added responsibilities.

Tommy sets Kristin up on a date with a salesman from the cell phone store who is also short. When she doesn't like the guy, he won't take the hint to leave her alone.

Tommy finds out that Kristin once spent the night in jail, he contacts someone from her past to get the dirt on her. When he uses the info to play a prank on her, she decides to get him back.