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Episode 1

I Love You... Soon

Synopsis

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.

Episode 2

30 Mins

Boys' Club

Synopsis

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.

Episode 3

30 Mins

When Holly Met Tina

Synopsis

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.

Episode 4

30 Mins

The Loft

Synopsis

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.

Episode 5

30 Mins

Like a Virgin (Kinda)

Synopsis

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.

Episode 6

30 Mins

No More Mr. Nice Guy

Synopsis

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.

Episode 7

30 Mins

I'm Sorry, So Sorry

Synopsis

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.

Episode 8

30 Mins

Partially Obstructed View

Synopsis

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.

Episode 9

30 Mins

Absence Makes the Heart Grow...Never Mind

Synopsis

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.

Episode 10

30 Mins

The Odd Couple

Synopsis

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.

Episode 11

30 Mins

Regarding Henry

Synopsis

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.

Episode 12

30 Mins

The Incredible Shrinking Group

Synopsis

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.

Episode 13

30 Mins

The Hospital

Synopsis

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.

Episode 14

30 Mins

Your Cheatin' Heart

Synopsis

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.

Episode 15

30 Mins

Sky Rink Sucks

Synopsis

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!

Episode 16

30 Mins

Lunar Eclipse of the Heart

Synopsis

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.

Episode 17

30 Mins

Val and Holly's Not-Boyfriends

Synopsis

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.

Episode 18

30 Mins

The Interview

Synopsis

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'.

Episode 19

30 Mins

The Big Picture

Synopsis

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.

Episode 20

30 Mins

Rollin' in It

Synopsis

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

Episode 21

30 Mins

The Anti-Prom

Synopsis

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.

Episode 22

30 Mins

The Second Season Finale (1)

Synopsis

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.