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.