Holly has a crush on a college guy who drops by her work everyday and gets invited by him to a college party when she slyly swaps her cell phone with his then calls him to innocently ask where they should meet to swap them back.
While Jeff is out of town, Holly takes Val on a night out. However, the female bonding stops when Hunter, a guy Holly wants to date, makes a romantic advance on Val. The situation gets worse when Hunter's jealous girlfriend, Sasha, arrives.
Jeff's mother comes for a visit. He asks Val to take her out. And after going out with Val, Jeff's mom decides to leave her husband. And Holly and Gary go to a concert and when she sits on Gary's seat, someone comes along who says that the seat was chosen as the winner of an Ibop. When Gary learns of this, he's irate with Holly, who doesn't think it's his.
On Valentine's Day, Holly thinks that Jeff is planning to propose marriage to Val. Meanwhile, Gary gets a date with a great girl, but the pressures of the holiday overwhelm him, and he insists that Holly come along with her date.
When Holly spends all of her money on an expensive sweater, Jeff agrees to hire her as a waitress, Holly's first job. But he regrets his decision when Holly wreaks havoc in the restaurant and even causes the chef to quit.
When Val returns from a romantic skiing trip, she astounds Holly by announcing that she has ended her relationship with Jeff. Holly tries everything she can to help her sister cope with her feelings, but Val's neuroses soon become unbearable.
Holly and her friend Henry (MICHAEL McMILLIAN) skip school and "borrow" Val's car, but they panic when the car is discovered missing. Meanwhile, Gary helps Jeff gain a new restaurant management job but expects free food in return.
Holly encourages Val to loosen up and mingle with her co-workers. And she talks about something that happened to her which makes her the life of the party. When her boss Vic brings her home, she thinks he's making a move which she nixes. The following day things between them are weird at the office. Jeff is dating an older woman whom he later learns is Gary's mother.
When Holly meets Henry's brother a doctor, she decides to set him up with Val. When Henry learns of her plans, he tells her that's not a good idea and does't tell her why. But she does it anyway. When Henry learns what she did, he shows her why he didn't want her to do it but they choose not to tell Val.
When Val's vindictive neighbor, Mindy, finds out that Val never got approval for Holly to move in, Mindy persuades the tenant board to evict Holly. After checking out some of the disgusting apartments that they can
In order to help Val get her first client, Dr. Judith Haven, since starting her own public relations firm, Holly becomes friends with the clients troubled teenage daughter, Tina. Meanwhile, Lauren tries to distract Peter away from Judith for the new account and gets drunk in the process.
Val is looking for a new apartment so that she can set up her business. Holly learns from Tina of an apartment that she maintains for the owner who is in prison for a white collar crime, which is fabulous. Holly tries to get Val to get it but Val doesn't think she can afford it. Holly then goes to see the man and refuses. But when Holly learns that he hasn't spoken to his daughter since he was arrested, Holly tries to get her to see him hoping he will grateful and let them have his loft.
Holly is shocked to learn that Henry has already lost his virginity, and her decision to find out about his former girlfriend leads to some disturbing information. Meanwhile, Lauren devises a plan to get Val to relax and take a day off from work.
Val confronts Holly about neglecting Henry and spending too much time with cute messenger Vince. Holly reacts by pointing out Val's hypocrisy, and she challenges Val to examine her own feelings for Peter, her handsome former boss.
Holly's plans for a skiing weekend with Henry and their friends come to a halt when Tina and Cal end their relationship. Holly must decide if she should spend the weekend on the mountain or respect Tina's wishes and not go.
When Vince arranges for Holly and Tina to go to a band rehearsal, Holly becomes caught in a series of lies. She must make up a story after Henry finds out that she got front-row seats to a concert by his favorite band.
Holly thinks she's ready to tell Henry that she loves him, but she hesitates after she considers her lingering feelings for Vince. Meanwhile, Val's first business trip out of New York City is surprising when Peter becomes her neighbor in the hotel.
Holly searches the city for Henry after he ends their relationship when he overhears her confessing to Val that she is attracted to Vince. Holly's life becomes even more complicated when Vince find outs about Holly's secret feelings.