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.

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 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.

Holly lands a job at a copy shop where she thinks her new co-worker, Jake, is interested in her, but when she takes Jeff's advice on how to handle the situation, she becomes the laughing stock of the store. Meanwhile, Val is nervous about landing a new account and impressing her prospective new client.

Holly has a major crush on a cute college guy named Evan and he's been coming in everyday at "Copy That" to get some coffee but Holly gets a chance to actually know him when she "accidentially" takes Evan's cell phone and gets invited to a college party to swap phones. Gary wants to come too, but Holly doesn't want him to interfere. However, despite Holly's wishes, Gary shows up at the party as a co-ed to get in with the college girls. Meanwhile, Val starts to get a little competitive at Scrabble.

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.

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.

Valerie breaks up with Jeff after he says he doesn't want to get married, and she tries to bury her pain under a veneer of optimism. Holly then tries to get her sister to drop the act and face up to her pain.

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.

When Holly meets Henry's older brother, Noah, she instantly assumes that he and Val would be a great couple. Despite Henry's asking of Holly not to fix them up, Holly fixes Val and Noah up anyway, and eventually finds out why Henry asked for them not to be fixed up.

Val and Holly meet a resident who would've got their apartment 5 years ago, but got a smaller one. So she threatens to evict them. Meanwhile, Gary thinks Holly forgot her birthday when she gives him a cheap present. So Gary gets mad at Holly for it, not knowing that that wasn't the only present.

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.

In the second season premiere, Holly tries to help Henry overcome his jealousy of Vince, an eccentric older guy who works at Harper and Diggs, but she makes matters worse when she accidentally tells Henry that she loves him. Meanwhile, back at the office, Val finds herself attracted to Peter, her handsome and charming new boss.

Holly begins to feel the pressure of school, work and friends, so it is hard for her to be there when Henry needs her the most. Meanwhile, Val gets upset with her boss' business antics and the new boys' club atmosphere that the business has taken on so Val takes matters into her own hands and quits.

In order to help Val get her first client since starting her own public relations firm, Holly becomes friends with the client's troubled teenage daughter, Tina. Meanwhile, Lauren distract Peter when they find themselves in competition with their former boss for the new account.

When Val thinks it's time to move into a new apartment with bigger office space, she and Lauren look for apartments. When Tina shows Holly a loft in her building, Holly thinks it's wonderful. Things get better for Holly when she finds out that the guy (Jay) is in prison. Holly and Val try to compromise with the guy to buy his loft. The Tyler sisters don't get Jay's loft, but Jay offers them another loft in the same building.

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 Tina's boyfriend Cal gets a condo up in the mountains, the gang makes plans to go away for the weekend on a ski trip. But when Tina and Cal have a fight, the ski trip gets canceled. Holly gets mad because she really wanted to go on the trip, but when Cal says everyone but Tina can go, Holly decides she wants to go. Tina takes her anger out on Holly because she invited Vince, when she knows Henry will be there. Meanwhile, Val and Lauren get into a fight because Lauren's new boyfriend likes Val better and invites her out for drinks. Holly decides that being with her best friend is more important than skiing with Henry, Vince, Gary, and Cal, so she cancels on the gang and spends the weekend with Tina.

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 tries every attempt to find out if Henry has a new girlfriend so she can go after Vince. It turns out that Henry has moved on. When Holly goes to Vince's, she finds something she wasn't expecting. Meanwhile, Val and Lauren run into Rick (Val's ex-boyfriend) while they are at the diner. They make lunch plans, and reminisce on old times.

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

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 returns home from Paris with Ben, a handsome British musician who has stolen Holly's heart.Vince and Henry Realizes they've losted Holly, Henry says goodbye to Holly one last time before leaving for Princeton. Meanwhile, Val, who has spent the summer with Rick, receives a surprise proposal after she reveals her own surprise.

Holly moves out of the loft with Ben when Val tell her that Ben can not live in the loft with them. Holly and Ben then end up at Vince and Gary's apartment, Vince agrees to let them stay there, Meanwhile, Val is concerned her fear of commitment is affecting Holly and wonders if she did the right thing by breaking off her engagement with Rick

Holly works so hard to try to help Ben's music career, that she risks their relationship when she uses her money for school books to pay for Ben to perform at a club, where pop star Jesse McCartney is performing. Meanwhile, Rick asks Lauren to help him shop for the a ring for Val , Lauren chooses the perfect ring but she chooses for herself.

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...!

When Val comes to the conclusion that she can't go through with the wedding, she takes her anger out on Holly. Meanwhile Holly was thinking she would not go on tour with Ben, because Val needs her, but because Val is mad at her she decides to go. On her way to the train, Holly realizes why Val was angry, and decides that she can't go with Ben. Also Gary finds out Vince and Tina slept together.

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.

An upset Holly comes into the bakery on Valentine's Day at 5 in the morning, worrying about the day before when she said "I love you, Vince." to Ben. Meanwhile, Lauren is cranky on V-Day because she has no boyfriend to share it with; and her crankiness is driving away customers.

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.

Val yells at a crabby old man at her bakery, then he ends up dying a minute later. Val thinks his death is her fault, and Lauren tells her to go to the man's funeral to feel better. Val finds out that Lauren only told her to go to the funeral so she (Lauren) could pick up guys. Meanwhile, Holly gets Tina a job where she works, then Tina uses her body to get a higher position. Holly disagrees with Tina's flaunting and says they're no longer friends. Val and Holly, both mad at their friends, decide to tell Lauren and Tina that they just have low self-esteem. This works out for the most part, and everyone becomes friends again.

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 calls a radio psychologist to ask about her relationship problems. The psychologist tells her to talk to her past boyfriends. Lauren breaks a pipe and calls Todd. Holly goes to see Henry at Princeton for help because she does not want to talk to Vince. Vince heard the psychologist talking to Holly and thinks she is going to come and see him.

Val, crushed over Rick's getting married to Julie again, wakes up the next morning married...to the plumber. Tina plans a vacation to Europe, but when her mom gets sick, Tina is stuck with an extra plane ticket, leaving Gary and Lauren fighting over who will go. Meanwhile, Holly takes drastic steps to reconnect with Vince.

After waking up to find a wedding ring on her finger, Val is surprised to learn that she has married her Old Boss, Vic, during a wild night in Atlantic City. Meanwhile, Holly has hidden out in the back of Vince's car as he travels to Florida to tell him she loves him, but is heartbroken when she realizes she may have lost him forever.

In Part 1 of a two-part episode, Jason Priestley plays a man who asks Val on a date, which she sees as a perfect way to distance herself from Vic; and Holly and Vince have a fight over jealousy.

When Holly feels that she is ready to take her relationship to the next level with Vince, she is determined to make Vince feel the same. Meanwhile, Charlie proposes to Val, who doesn't want to tell him that Vic is actually her husband. When Vic feels like the 'monkey in the middle,' he decides that he and Val should take a break from each other. Then Val realizes she really does need Vic.

It's Jazz Night at the bakery and Val finally asks Vic to be her date to the party. Though he initially agrees to the date, things go awry when he shows up with annulment papers, but the signing is delayed when Lauren spills champagne on the papers. Meanwhile, Holly persuades Vince to shave his beard by threatening to not shave her legs.

Val runs afoul of Vic's firefighting pals when she withdraws the bakery's offer of providing them with free food and coffee; Tina and Gary try to patch things up between Holly and Vince.

Val panics when she learns that she and Vic were not legally married. Required to wait 24 hours by City Hall before they are allowed to have a civil ceremony, they decide to take a compatibility test, resulting in a fight about how many kids each of them want to eventually have. Meanwhile, Holly is worried she broke up with Vince too quickly, but having spent time at Vic's family reunion, she realizes she did the right thing.

In the series finale, Valerie finally has her dream wedding to Vic, but there are a few problems. Val, Holly, and Lauren are stuck at a spa where an escaped convict is being searched for, making the three of them late for the wedding.