Holly has to convince her old sister, Val, to allow her to stay with her instead of going to Japan with thier father.
Holly tries to prove to be a capable roommate and also cost Val her job when an encounter with Tony Hawk goes wrong.
Holly tries to be at two places at once after learning JC from N'SYNC is appearing at a record on the same day she and Val have a spa day.
Val and Holly begin to question their roommate situation as both have issues with each others habits.
Holly and Val battle over a teddy bear from thier childhood. They decide to give the bear to a girl in the apartment until the little girl displays an ungrateful behavior afterwards.
Holly takes advantage of Val, after she is given more freedom to doing things. Which happens to include staying out all night long.
Holly uses protesting for animal rights to get closer to a boy named Kyle.
When Holly's old friend, Samantha, comes to visit, Gary is the odd man out and Jeff doesn't like Val sleeping in
ex-boyfriend's sweat shirt.
Holly and Gary work together at a copy shop and Val is nervous as she tries to land a new client.
Holly and Val seek to start a new Thanksgiving tradition without thier relatives, however those same relatives start showing up.
Holly get invited to a college party after returning a misplace cellphone. What she didn't expect was Gary showing up pretend to be a college student.
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 and Val go out for the night while Jeff is out of town. The bonding stops when Hunter, a guy Holly has a crush on, hits on 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 Jill, but the Valentine's Day pressures overwhelm him and he insists Holly and Michael double date with them.
When Holly wants 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.
Val breaks up with Jeff after he tells her that he isn't interested in marriage.
Holly decides to skip school with Henry and go to the beach in Val's car. However during the trip the car is stolen.
Holly convinces Val to socialize with her coworkers as Jeff is attracted to Olivia, who happens to be Gary's mother.
Holly tries to play matchermaker with Herny's brother, Noah, and Val despite Henry's objections.
A resident tries to get Holly and Val to give up their apartment. Meanwhile Gary is fuming about the cheap birthday gift Holly gave him.
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 Jill.
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 get 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 clients troubled teenage daughter, Tina . Meanwhile, Lauren distract Peter when they find themselves in competition with him 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. Holly and Val try to comprimise with Jay 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 Shannon, Henry's first. Meanwhile, Lauren tries to get Val to relax and take a day off from work by faking her brithday.
Val accuses Holly of spending more time with Vince then Henry when Vince helps her set up Val's barbeque on the terrace. Holly and Vince fall asleep, and Holly wakes up in Vince's arms.Holly assures everyone that they didn't have sex, as she realizes that se 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.
Henry is away at Princeton and Holly misses him, so she tries to surprise him by going to Princeton. Meanwhile Gary gets some disturbing news from Jill, after she returns from her trip to Paris.
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 theings go wrong when he doesn't show up, and nobody can find him.
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.
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 he has to go to the hospital. Holly, Val, Lauren, and Tina go to the hospital to see him. Holly sees Vince. Meanwhile, Val and Lauren meet a handsome doctor named Dr. Turner.
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 faster than Holly expected. 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.
It's Gary's birthday and Holly discovers something about Gary's ex-girlfrind, Jill. Jill has lied about leaving the country in order to dump Gary. Now she and Vince have to deal with the fact of telling Gary.
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 rude to 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 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 recieve $10,000 in cash. Holly questions the breakup between her and Henry.
Holly gets $2,000 for her birthday and instead of saving it for college like Val wants her to, she gets lavish hotel room.
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 befor 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.
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.
When Ben has a gig the same night as Val's Bachelorette Party, Holly decides to change its date.
Meanwhile Gary falls for a dancer named Danielle.
Holly and Tina enter The Herbal Essence Contest for different reasons. Holly wants money for Val's wedding gift adn Tina does it to spite Holly, who objects to her relationship with her boss.
Holly lies to Ben about his song being good to prove that she loves him. Things go from bad to worst after he sends the song to a producer. Meanwhile Val has to deal with Rick adn his odd 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 takes exceptio to Ben's female fans googling over him. Val tries to make everything right for when Rick's mother vists.
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
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.
Vince uses Ben's busy schedule to get closer to Holly. Val discovers that Lauren has bankrupted her company and she has to start over again.
Holly adds a new female singer anmed Amber to Ben's band. She soon regrets it after Amber is interested in Vince. Lauren uses Val to get good reviews of the bakery by setting her up with a food critic.
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.
Val takes advice from Fran Reeves about dating younger men and ends up going to a prom with a high school student. Holly and Vince fight over thier friends by using gifts.
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 Lauren could pick up guys. Meanwhile, Holly gets Tina a job where she works, then Tina uses her body to get a higher position.
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! Meantime, worried that she's too stodgy, boring, and neurotic, Val buys a Porche...then goes nuts trying to keep her wild impulve "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.
After waking up to find a wedding ring on her finger, Val is surprised to learn that she has married her Plumber, Toad, 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.
Holly and Vince now an official couple, Holly is determined to maker her relationship work even though they must spend a few months apart while Vince is in Florida. Meanwhile, Val and Lauren devise a plan to force Val's new husband Vic out of her apartment so they can end their "quickie" marriage.
Holly and Vince have their first fight when Vince takes Gary to a basketball game instead of her. Holly feels that she and Vince should attend sporting events, plays and other events together, though she quickly realizes this idea may not be for the best. Vic still refuses to sign the annulment papers, but it seems that his persistence may be winning Val over.
Tina admits to Holly that she may have feelings for Gary. gary tells Vince the same thing. Things go bad when Holly and Vince reveal it to each other by accident.
Val tries to convince Vic that their marriage is meaningless by going out on a date with Charlie, a customer in the bakery. Though Charlie quickly becomes obsessed with Val, the date causes Val's feelings for Vic to deepen. Meanwhile, Holly demands that Vince clear out the phone numbers of all females in his cell phone, resulting in an argument that involves Gary and Tina.
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.
Jack Tyler drops in from Japan with some news about his new business and business partner.
It's Jazz Night at the bakery and Val finally asks Vic to be her date to the party. He agrees to the date and things go awry when the lawyer shows up with annulment papers, Lauren spills champagne on the papers to allow Val and Vic to talk.
On Thanksgiving, Holly and Vince discover Lauren kissing Rick, Val's ex-fiancé, and do their best to hide the truth from Val. Meanwhile, the situation leads Val straight into Vic's arms and the two decide not to sign their annulment papers.
Vince feels like less of a man when he learns that Holly makes more money than he does. In order to help Vince, Holly decides to polish up and submit Vince's resume to companies without his knowledge. Meanwhile, Val is excited about her first official date with Vic (guest star Dan Cortese), but a fight with Lauren distracts her from showing up on time. Val's guilt for missing the date turns to shock when she learns that a dangerous fire has injured numerous firefighters.
Now that Vic has returned home from the hospital following his accident, Val has to wait on him hand and foot and even give him sponge baths. When they both learn they are not allowed to take their relationship to the next level for six weeks, the situation grows tense.
Meanwhile, Holly's jealousy over Vince spending time with his new co-worker ends up costing him the job.
Lauren lies about a surprise party for Valerie so she can see Rick, but the truth comes out when the affair lands Rick in the hospital, and Val cannot forgive her friend for the deceit. Meanwhile, Vic has a special gift for Val, but has trouble finding the perfect time to give it to her.
When Val meets Vic's mom, Eileen, for the first time, she does her best to impress her. In doing so, Val unknowingly causes her mother-in-law to fall off the wagon. Meanwhile, Holly's jealousy over Vince's new partnership with his co-worker causes them to re-evaluate their relationship.
Holly and Vince fail to see eye-to-eye regarding his new working relationship with his female co-worker and decide to spend some time apart. Meanwhile, Vic receives a clean bill of health from the doctor and he and Val are finally able to take their relationship to the next level. However, when Val decides to abruptly end her newly created special offer - free coffee and food - for Vic's firehouse, it causes a rift in their relationship.
Val and Vic learn that they are not legally married. SO they are forced to wait 24 hours before getting married in a civil ceremony. Elsewhere Holly is having regrets of breaking up with Vince until she meets his family.
Val and Vic plan to finally consummate their relationship, but a romantic evening is ruined when Holly, upset by Vince, turns to Val for comfort. In order to get away, Val leaves Lauren in charge of Holly, but the two of them end up behind bars. Meanwhile, Vince accepts a new job in Chicago.
The day before the wedding, Lauren treats Val, Holly and Tina to a spa day to celebrate the big event. Upset over Vince’s decision to move to Chicago, Holly has yet to learn that Vince finally realizes that his co-worker has feelings for him.
The girls are trapped in a spa, but Holly and Val commandeer a horse in an attempt to make it to the wedding on time. Meanwhile, Gary and Vince say good-bye to each other, as Vince heads to Chicago for a new job. Vic and Val finally tie the knot, Holly has a surprise visitor, while Lauren, Gary and Tina all find love.