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When her father accepts a job overseas, high-spirited 16-year-old Holly has no plans to head to Japan with him. She decides she'd rather live in the Big Apple 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 Valerie'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 sticky 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. Meanwhile, Jeff and Gary have an afternoon of male competition after Gary calls Jeff old.
When Holly's unintentionally disruptive antics finally become unbearable, Val creates a G.R.C.a Good Roommate Chartfor Holly to follow. Afraid of being sent to live with her father in Japan, Holly strictly adheres to the obsessive regulations, but a mishap involving Gary and dozens of Val's stuffed animals might just mean the end of this living arrangement. Meanwhile, Val and Jeff think they've found the perfect opportunity for some much-needed romancebut Holly's violation of the G.R.C. ruins that plan.
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.
Valerie decides to stop henpecking Holly and give the teen more freedom, but her new strategy backfires when Holly tries to stay out all night without telling Val where she's going.
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 takes a job at a copy shop and thinks that her new co-worker Jake is interested in her. But when she follows Jeff's advice on how to deal with the situation, she becomes the laughingstock of the store. Meanwhile, Val is nervous about acquiring a new account and impressing her prospective new client, Paul Cody.
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 is enamored with college student Evan, who frequents Copy That, the photocopy shop where she works. After Evan accidentally takes Holly's cellular telephone instead of his, she calls him and accepts his invitation to a party at his apartment. Concerned about Holly attending a college gathering, Gary insists on accompanying her. While Holly dances with Evan, Gary finds out from a group of girls that Evan is a notorious womanizer and tries to warn Holly before it's too late. Meanwhile, Val and Jeff learn a lesson about their relationship during a board game.
Holly becomes pals with Jeff's ex-girlfriend, despite Jeff's warnings that such a relationship could be troublesome. Meanwhile, Gary saves the life of a real-estate magnate at a concert and receives an unusual reward.
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 impulse, 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 iPod 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 a friend 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 Oliviabut is shocked to find out that she is Gary's mother.
Holly fixes up Val with Henry's brother; Jeff hires both Gary and Jill.
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, Valerie lectures Holly about sex, but a chance encounter with Jeff makes her look like a hypocrite. Meanwhile, Gary keeps ditching Holly to spend time with his girlfriend.
Holly tries to help Henry overcome his jealousy of Vince an eccentric older guy who works in Val's office,but she makes matters worse wheb 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 their former boss for the new account.
Holly get a rich, incarcerated man to let her and Val move into his loft so that Val can have her own office.
When Holly learn that Henry has already lost his virginity she is shocked.Lauren tryes to get Val to relax and take a day off form work.
Val confronts Holly about neglecting Henry and spending too much time with cute messenger Vince. Holly reacts by pointing out Val's hypocrisy, and challenges Val to examine her own feelings for her handsome former boss Peter.
Holly's get plans messed up when a friend needs her after a breakup; Lauren's new boyfriend becomes very smitten with Val
Henry finds out that Holly has got front-row seats to see his favorite band;meanwhile Val bumps into Peter at a party for the city's most eligible bachelor
when on a business trip Val unexpectedly runs into Peter and finds out he has the hotel room next door; Holly realizes she has feelings for Vince
Holly feels pulled in different directions when Henry in moves with Vince for a little while; Lauren convinces Val to try speed dating.
Holly scours the city for Henry after he breaks up with her.
Holly and Garys is put to the test when she ask him to set up a meeting between her and herny.
Holly unwittingly causes Vince to get into a traffic accident.
Holly tries to determine if Henry is seeing anyone new so she can go after Vince.
Holly and Vince are at odds trying to coordinate Gary's birthday party.
A Valentine's Day excursion to see a lunar eclipse is shared by Holly, Greg, Gary, Tina, Vince and Liz.
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.
After a disastrous first meeting with the admissions director, Holly gets coaching from Val as she tries to get into Columbia University.
Val meets Rick's fiancee Julie and finds out they're not as compatible as she thought they were, and Holly gets help from Henry as she writes an important essay.
When Holly receives $2,000 from her grandmother for her 18th birthday, she decides to blow it on a lavish hotel suite.
Dateless Holly and Tina decide to throw a party on prom night. And Val doesn't know what to make of it when she receives an invitation to Rick and Julie's wedding.
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.
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.
The group celebrate Halloween, by going to a party wear Holly and Ben dress up as Sonny & Cher, Gary and Danielle as Ike & Tina Turner and Tina and Vince as Homer Simpsons 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 and Ben have a difficult time balancing their professional and personal relationships, so Holly ask's Vince for help on a scheme to set things right. Meanwhile, Val is given very short notice that Rick's parents are coming for dinner and she insists making his mother's favorite meal.
The wedding is almost here, and everyone is nervous. Ben gets a contract to go on tour, and Holly can go with him, and she decides to go. Vince is furious. Tina is going out with her married boss. She thinks it's a date, but it's not. 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. Vince and Tina, keeping quiet of what happened, try to help her. She tells Val, but makes it clear that his ex was the one who called him. The day of the wedding, Vince and Tina are nervous, they try to continue being quiet. Holly has to go see Rick's ex, so she goes, and Vince and Tina cover for her. Rick's ex, who was at her psychiatrists' at the time, tells Holly that Rick called her, not the other way around. Holly gets to the wedding just in time to walk Val down the isle, while Gavin DeGraw is singing. As they are walking down the isle, Holly tells Val that Rick called his ex, Julie. When Val hears this, she stops walking, and the episode ends.
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. 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 here business in to the ground, and realizes that it is time for a change.
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 boobs 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.