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.

Holy moves up Vals Bachelorette party, because Ben has a gig the same night, Val gets upset and bumps Holly from the position of Maid of Honor, leaving Lauren to be the Maid of Honor.

When Holly enters a contest to become the new "Herbal Essences Girl" to earn money for Val's wedding gift, Tina, who is mad at Holly, enters against her. Val finds a love letter Rick has kept from his ex-fiancé, and gets worried.

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.

The group celebrate Halloween, by going to a party at the diner where Holly and Ben dress up as Sonny & Cher, Gary and Danielle as Ike & Tina Turner and Tina and Vince as Homer Simpson and Jessica Simpson. Everyone is shocked when they find out Holly dropped out of college. Meanwhile, in order to get Val to relax, Lauren takes her to a 'dude ranch' that turns out to be a nude ranch.

Holly starts feeling jealous of some of Ben's fans, so she tries to make Ben jealous in return. But when Holly's plan does not work Vince steps in with an idea of his own. Also Rick's mother is coming to visit, and Val wants her soon-to-be mother in law to like her, so she goes crazy trying to get everything just right.

Val is acting very anxious because her wedding is coming up soon. She becomes even more anxious when she finds out that her dressmaker, Gittle has died and that her wedding dress has been given to a thrift store. Holly, Vince, Gary, and Ben go to the store to get the dress back but to their disappointment, the cashier just sold it. Meanwhile, Holly, Ben, and Gary see Rick having pizza with his ex-fiancee, Julie at the pizzeria next door to the thrift shop, when he told Val that he was in New Jersey on business.

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 is really excited about her new job, until she gets there and thinks her boss hates her. Val is having trouble moving on, after braking up with Rick, so Holly takes her to a club. At the club Val meets a woman who is going through the same thing. Meanwhile when Holly runs in to her boss, who we find out is a lesbian, while she is dancing with Tina so her boss assumes Holly is also a lesbian, and now that her boss likes her Holly can't find away to tell her she's not.

When Holly gets annoyed at Ben for spending so much time on his career, and not enough time with her, Vince takes advantage of the situation by spending more time with Holly. Also Val finds out Lauren has run her business in to the ground, and realizes that it is time for a change.

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 wants Ben to yell at her for breaking his heart and when he doesn't, she gets upset with him. Finally, he writes a nasty song about her and wants to sing it during his performance at the club. Elsewhere, Val allows Lauren and Gary to watch the Sugar Baby Bakery while she goes out to lunch with Holly and they get robbed...By a 10 year old.

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.

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 piss 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.

Holly tries to set Ben up with a girl he likes because she thinks she made Ben lose his bravery when she broke up with him. She fails and needs Vince's help, but the problem is that Vince doesn't want to be her friend anymore. They end up confronting each other and become friends again. Meanwhile, Val hires a hobo to work at the bakery, and both her and Lauren end up liking him. After they try to go on a date with him, the hobo tells them that he's married.

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 plans a romantic surprise party for Vince's birthday but when he arrives with a date havoc erupts when Vince tries to get Holly to admit that she can't make a commitment. In the meantime, Val meets a handsome single dad and has high hopes of becoming an instant family until she realizes the chemistry in the relationship is between herself and the man's 8-year-old son.

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.

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.

When Holly learns that Henry has already lost his virginity she is shocked. She and Tina go and search the city frantically for the girl that 'soiled' Henry. Meanwhile, Lauren tries to get Val to relax and take a day off from work by faking her birthday.

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.

Holly and Tina plan a girls' night out while Henry and Gary plan a boys' night out. Vince sees Holly and Tina at the diner and hooks them up with free front row tickets to The Strokes' concert. Henry tells Holly that he has tickets to The Strokes, but they have a partially obstructed view. Holly wants to tell Henry how she got her tickets, but he says he stood in line for 12 hours waiting for his tickets. Meanwhile, when Val finds out that Peter is number 2 on the "New York's 10 Most Eligible Bachelors" list. Lauren sets Val and Peter up by forging a letter requesting tickets to the party.

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.

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.

After Henry overhears Val and Holly talking at the diner about Holly and Henry's relationship, Henry breaks up with Holly. Holly is so upset, she doesn't know what to do. So, she scours the city looking for answers while Val refuses to help her.

Holly and Gary's friendship is put to the test when Holly asks Gary to meet her with Henry at the movies. Meanwhile, after discovering that she ate seven Mounds bars and woke up with chocolate cake in her cleavage, Val decides it's time to go on a no-sugar diet, with Lauren as her partner.

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.

Holly and Vince try to be friends again by throwing a surprise birthday party for Gary's 18th birthday. When Holly and Vince run into Jill (Gary's ex-girlfriend) at the diner, who is supposed to be in Paris. They find out that for six months, Jill was really in New York! Holly and Vince argue whether or not to tell Gary about Jill - especially on his birthday. Meanwhile, Rick and Val keep visiting each other, and Lauren keeps bragging about her new boyfriend-who is a doctor!

When Holly and Tina are shopping at F&A (Gary's new workplace), Holly meets Greg, Gary's manager. Greg asks Holly out on a date, and she accepts, just to make Vince jealous. Everyone decides that they're going to Holly's house to see a lunar eclipse, and that's when everyone's true feelings come out.

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.

Val and Holly prepare all week for Holly's interview to get into Columbia University. The day before the interview finally comes, when Vince announces that he can invite as many friends as he wants to go to Coney Island with him to test out the new rides there. Holly skips the interview and tries to reschedule when she learns that the earliest opening is Tuesday, March 15th, 2005. Meanwhile, Lauren considers ending her relationship with Brad 'the doctor'.

Val meets Rick's fiancee when he and Julie come to dinner. Julie and finds out that she and Rick are not as compatible as she thought they were. Meanwhile, while writing her college report, Holly forgets to save it, and it gets deleted! She asks Henry for help, and he does, which causes him to not meet his idol Bill Joy and receive $10,000 in cash. Holly questions the breakup between her and Henry.

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

When Holly and Tina don't have dates to the prom, they are upset, so they decide to throw an Anti-Prom, with no decorations, no dresses, and no prom king or prom queen. Everyone who doesn't have a date shows up, but when Henry comes with Kate, Holly is heartbroken. Meanwhile, Val doesn't know what to do when she gets an invitation to Rick and Julie's wedding. She tries to look at the post mark to see if it was sent before Julie's "no contact" rule, but the postmark is smudged.

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.

When her father accepts a promotion overseas in Japan , high-spirited 16-year-old Holly has no plans to head to Japan with him. She decides she'd rather live in the New York City with her "straight-laced" sister, Valerie. In the opener, Holly's attempts to prove herself a perfect roommate backfire when she misinterprets a remark about Feng Shui and rearranges the apartment. To make matters worse, Holly jeopardizes Val's job with a marketing firm when she disrupts a promotional event featuring skateboarder Tony Hawk.

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.

Val has trouble adjusting to Holly's care-free attitude, so she makes her follow a strict set of rules. Holly does her best to follow them, and realizes that she just can't do it. This leads Holly and Val ti the conclusion that Holly is nothing like Val, which is why it is hard for Holly to adjust to the rules that Val has carefully thought of and made up. So Val and Holly question why they ever became roommates.

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.

Gary feels left out when an old female friend comes to visit Holly, but Holly gets a surprise when she catches the pair making out. Meanwhile, Jeff is bummed when he discovers that Valerie still sleeps in an ex-boyfriend's sweat shirt.

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.

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. Meanwhile, Jeff and Gary go on a mission to find the perfect turkey for Val.

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.

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.

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.

Jeff suggests that Val should be more spontaneous and impulsive, but his advice backfires when Val who is dressed like a sexy cheerleader, is caught by Jeff's mom who has unexpectedly come to town. Meanwhile, Holly and Gary are at odds over a free "iBop" that Gary insists belongs to him.

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.

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.

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.

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.