Holly promised Val a girls day out at the spa, forgetting she had promised her friend to go see J.C. Chasez from NSYNC on the same day, so tries to sneak out of the spa to quickly meet J.C. and get back to the spa without Val's knowledge.
Holly and Valerie both claim to be the righteous owner of a teddy bear found in the closet. Because they can't settle it out, they decide to give the bear to Josie, a young next door girl, but soon regret it.
Holly is excited to form a trio with her longtime pal, Samantha, and current best friend, Gary. When Gary feels neglected because of all the girls' shared memories, Holly advises him to give Samantha a chance.
Holly gets a job at the copy place where Gary works. One of the guys hits on her but she rejects him. But he tells the others that she wanted him and when he rejected it couldn't accept it. Now Val has a meeting with a client and her boss plans to join but she wreaks of a bad odor and Val tries her best make sure she doesn't when they meet him.
Determined to start their own Thanksgiving tradition, Val and Holly cancel plans with their relatives, claiming that Holly is sick. However, the girls' happy day goes awry when the family arrives at their apartment to surprise them.
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