While Jeff is out of town, Holly takes Val out on the town, but the female bonding stops when Hunter, a guy Holly has her eye on, makes a pass at Val. Things get worse when Hunter's jealous girlfriend comes looking for Val.

Holly's still mad with Tina for having a one night stand with Vince but she becomes furious when she learns that her own sister had a liaison with the Todd the plumber, which caused Val to miss Holly's comedy act at Giggles 10 years ago.

The kids play prank after prank on one another with impunity...but when one of Holly's (a fake eviction note) backfires and almost gets Ben kicked out of the country, Holly may have to become a bride to keep her British beau from being deported to the land of tea, crumpets, and Benny Hill! Meanwhile, worried that she's too stodgy, boring, and neurotic, Val buys a Porsche...then goes nuts trying to keep her wild impulsive "investment" pristine.

Holly is elated when she is accepted for an internship in Paris but when Henry and Vince each kiss her before she leaves she knows the time has come to decide between them. In order to distract her from Rick's upcoming wedding, Val books a trip to Venice with Lauren, but when Val gets sick and has to cancel, she is pleasantly surprised when a still-single Rick shows up at her doorstep. Meanwhile, it could be a summer of love for Gary and Tina when they have their second kiss.

Holly discovers that she loves Ben and that she wants to tell him, but she doesn't want to tell him that his new song is horrible, so she takes Lauren's advice and lies to him. All seems fine until Holly finds out that Ben wants to send his song to a producer. Holly then admits that she doesn't like Ben's song and Ben becomes upset with her: not because she hated his song but because she lied to him. Meanwhile, Val and Rick argue because she is having trouble adjusting to Rick's lifestyle.

Holly and Val battle over the possession of a stuffed teddy bear they both cherished during their childhood. But when the struggle for the bear becomes too much, the girls agree to give the critter to a little girl in the building, though after they discover she is abusive and destructive to their childhood treasure, they join forces to regain the bear.

Holly becomes smitten with a young man, Kyle, who is leading a protest movement to allow the zoo's performing parrot to retire, but things fly out of control when Kyle is so inspired by Holly's passion for the cause that he kidnaps the parrot. Meanwhile, Val plays matchmaker for a customer who reveals she has a crush on someone in the restaurant, until it is revealed that the object of her affection is Jeff.

When Henry is away at Princeton, Holly realizes that she loves him, and will go at any length to tell him in person. But things go wrong when Holly takes a train to Princeton, and Henry takes the train to Holly's house. Meanwhile on a business trip, Val winds up getting the hotel room next door to Peter's, and they wind up kissing.

Holly has partnered Ben with a hot new singer, Amber. But when Holly finds out the that Amber is attracted to Vince she starts getting a little jealous. To prove to herself that she is OK with it Holly suggests they go on a double date, Holly and Ben, and Vince and Amber. Meanwhile Lauren tries to insure that the bakery will get a good review by setting Val up with the reviewer.

Holly and Val plan a day of at the spa, but Holly finds herself in a 'muddy' situation when she sneaks out of the spa without Val's knowledge in order to meet J.C. Chasez from *NSYNC. Holly must somehow get back inside after being denied re-entry by a security guard. Being Holly, you know she always finds a sneaky way to do things, so she climbs in through a window landing in a mud bath with a naked lady! Meanwhile, Jeff and Gary have an afternoon of male competition after Gary calls Jeff old.

Holly volunteers to fill in at Val's office over spring break, but the girls clash over the tactics Val should use to land a promotion over a competitive colleague; Holly believes in playing dirty and kissing up to the boss and Val thinks her hard work and dedication will get her noticed.

On the most romantic day of the year, Holly jumps to the conclusion that Jeff is planning to propose to Val and Gary lands a date with a great girl, but the Valentine's Day pressures overwhelm him and he insists Holly double date with them.

When Holly sets her sites on buying an expensive sweater, Jeff agrees to hire Holly as a waitress but ultimately regrets his decision when Holly turns the restaurant upside down and even causes the chef to walk out.

In the first season finale, Val gets home from work only to find Holly and Henry in Holly's room---with the door closed! Val worries that Holly and Henry have slept together. She lectures Holly about sex. But when Holly comes home from the movies, she walks in to find only Val and Jeff in the shower together, making Val look like a hypocrite. Gary keeps ditching Holly to spend time with his girlfriend.

Val accuses Holly of spending more time with Vince than Henry when Vince helps her set up Val's barbecue on the terrace. Holly and Vince fall asleep, and Holly wakes up in Vince's arms. Although it seems (to Val and everyone else) that they had sex, Holly assures them that they didn't, and she realizes that she has feelings for Vince.

When Henry's parents kick him out, he moves in with Vince, making Holly feel awkward. Meanwhile, when Lauren realizes that Val hasn't had a boyfriend in a while, she sets her up by speed dating. Val meets a guy she really likes, and they plan to go out on a date. But things go wrong when he doesn't show up, and nobody can find him.

In this episode, Holly sends a fake package to someone to see Vince. They say hi and then Vince leaves quickly. When he is on his bike, a car runs into him and Vince ends up in the hospital. Holly, Val, Lauren, and Tina go to the hospital to see him. Holly sees Vince and Val and Lauren meet a handsome doctor.

Holly is puzzled by Vince's recent antagonistic behavior toward her until she learns the truth about why he was so brusque with her. And Val tries to sort out her feelings toward Rick.

When Holly receives $2,000 from her grandmother for her 18th birthday, she decides to blow it on a lavish hotel suite.

The wedding is almost here, and everyone is nervous. Ben gets a contract to go on tour, and Holly has the opportunity to go with him. Vince is furious. Tina is going out with her married boss (or so she thinks). She goes to Vince's afterward and they end up sleeping together. Holly doesn't know whether to tell Val of Rick's meeting with his ex. She tells Val, but makes it clear that his ex (Julie) was the one who called him. Julie tells Holly that Rick called her. Holly gets to the wedding just in time to walk Val down the aisle. As they are walking down the aisle, Holly tells Val that Rick called Julie. See you after winter sweeps for the conclusion of this episode...!

Fran Drescher drops by to give Val and Lauren some advice about dating younger men because Val goes out with a cute, intelligent, funny, and sweet guy. He seems totally perfect until Val finds out that he's still in high school.. Holly and Vince have a custody battle over Ben, Tina, and Gary. Holly may have forgiven Tina but she hasn't forgiven Vince. To top Vince, Holly takes Ben, Gary, and Tina to Cancun in Mexico, where she unexpectedly runs into Vince. Vince tries to p* off Holly by flirting with a ditsy girl and Holly reacts by saying that she and Vince can never be friends again. When Holly gets food poisoning, Vince takes care of her while the others go off to have fun. In the end, Holly wants to be friends with Vince again but Vince declines her wish by saying that he wants to be her boyfriend, not just her friend.

Val tries to ease up on being an authority figure to Holly, but her patience is pushed to the limit when Holly and Gary take off for a wild party on Long Island without letting anyone know.

Holly becomes pals with Jeff's ex-girlfriend, Dana when they both go to a U2 concert with Jeff, even though Val warned Jeff and Holly not to go with Dana, and Jeff never even wanted Holly and Dana to be friends. Meanwhile, Gary saves the life of a real-estate magnate at the concert.

Holly ditches school with Henry and borrows Val's car, but is shocked when she returns from the beach, to find the car gone! She tries to cover it up and act like it is gone, but Val soon finds out. They have a talk, and Holly admits to it, while Holly tells Val she has learned that Val takes $20 out of her allowance each week. Holly is mad, but then she finds out that, along with $30 of her own that Val puts in, that $20 is in a secret account for Holly's college. Jeff is trying to find a new job, when his dad decides to close their resteraunt.

Upon learning that Val has a reputation for being antisocial at work, Holly encourages her sister to mingle with her colleagues. However, an evening out becomes fodder for office gossip when Val finds herself in a compromising position with her boss Vic. Meanwhile, Jeff meets the attractive Olivia-but is shocked to find out that she is Gary's mother.