September 11, 2003 • 30m
In the second season premiere, Holly tries to help Henry overcome his jealousy of Vince, an eccentric older guy who works at Harpe...Read more
September 18, 2003 • 30m
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. M...Read more
September 25, 2003 • 30m
In order to help Val get her first client since starting her own public relations firm, Holly becomes friends with the client's tr...Read more
October 2, 2003 • 30m
When Val thinks it's time to move into a new apartment with bigger office space, she and Lauren look for apartments. When Tina sho...Read more
October 9, 2003 • 30m
When Holly learns that Henry has already lost his virginity she is shocked. She and Tina go and search the city frantically for th...Read more
October 16, 2003 • 30m
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...Read more
October 23, 2003 • 30m
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 whe...Read more
October 30, 2003 • 30m
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 hoo...Read more
November 6, 2003 • 30m
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...Read more
November 13, 2003 • 30m
When Henry's parents kick him out, he moves in with Vince, making Holly feel awkward. Meanwhile, when Lauren realizes that Val has...Read more
November 20, 2003 • 30m
After Henry overhears Val and Holly talking at the diner about Holly and Henry's relationship, Henry breaks up with Holly. Holly i...Read more
January 9, 2004 • 30m
Holly and Gary's friendship is put to the test when Holly asks Gary to meet her with Henry at the movies. Meanwhile, after discove...Read more
January 16, 2004 • 30m
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 hi...Read more
January 23, 2004 • 30m
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 o...Read more
January 30, 2004 • 30m
Holly and Vince try to be friends again by throwing a surprise birthday party for Gary's 18th birthday. When Holly and Vince run i...Read more
February 6, 2004 • 30m
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, a...Read more
February 13, 2004 • 30m
Holly is puzzled by Vince's recent antagonistic behavior toward her until she learns the truth about why he was so brusque with he...Read more
February 20, 2004 • 30m
Val and Holly prepare all week for Holly's interview to get into Columbia University. The day before the interview finally comes, ...Read more
April 16, 2004 • 30m
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 thou...Read more
April 23, 2004 • 30m
When Holly receives $2,000 from her grandmother for her 18th birthday, she decides to blow it on a lavish hotel suite.
April 30, 2004 • 30m
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 dr...Read more
May 7, 2004 • 30m
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...Read more