At a public relations firm, Val works closely with offbeat Lauren, but even in her position of respect, Val can't escape the occasional run-in with her acerbic--but very attractive--new boss, Peter.
Holly begins to feel stressed from juggling her schoolwork, job and friends--and Henry feels the pain because Holly doesn't support him when he has his wisdom teeth pulled.
In order to help Val get her first client, Dr. Judith Haven, since starting her own public relations firm, Holly becomes friends with the clients troubled teenage daughter, Tina. Meanwhile, Lauren tries to distract Peter away from Judith for the new account and gets drunk in the process.
Val is looking for a new apartment so that she can set up her business. Holly learns from Tina of an apartment that she maintains for the owner who is in prison for a white collar crime, which is fabulous. Holly tries to get Val to get it but Val doesn't think she can afford it. Holly then goes to see the man and refuses. But when Holly learns that he hasn't spoken to his daughter since he was arrested, Holly tries to get her to see him hoping he will grateful and let them have his loft.
Holly is shocked to learn that Henry has already lost his virginity, and her decision to find out about his former girlfriend leads to some disturbing information. Meanwhile, Lauren devises a plan to get Val to relax and take a day off from 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 she challenges Val to examine her own feelings for Peter, her handsome former boss.
Holly's plans for a skiing weekend with Henry and their friends come to a halt when Tina and Cal end their relationship. Holly must decide if she should spend the weekend on the mountain or respect Tina's wishes and not go.
When Vince arranges for Holly and Tina to go to a band rehearsal, Holly becomes caught in a series of lies. She must make up a story after Henry finds out that she got front-row seats to a concert by his favorite band.
Holly thinks she's ready to tell Henry that she loves him, but she hesitates after she considers her lingering feelings for Vince. Meanwhile, Val's first business trip out of New York City is surprising when Peter becomes her neighbor in the hotel.
Holly feels conflicted when Henry temporarily moves into Vince's apartment. When it appears that Tina is flirting with Vince, Holly must face her jealousy and figure out what--and who--she wants.
Holly searches the city for Henry after he ends their relationship when he overhears her confessing to Val that she is attracted to Vince. Holly's life becomes even more complicated when Vince find outs about Holly's secret feelings.
Holly comes close to destroying her friendship with Gary when she manipulates him into arranging a meeting with Henry, who is still upset with her because of her attraction to Vince.
After Vince is hit by a car, Holly visits him in the hospital, and they share their first kiss. However, they both realize that they can't date without hurting Henry's feelings.
Holly rushes to tell Vince that she saw Henry with another girl--meaning that Holly and Vince can date without feeling guilty--but her excitement turns to anger when she catches Vince in a compromising position.
Holly and Vince each have different ideas for celebrating Gary's birthday. However, their plans come to an abrupt halt when they discover that Gary's ex-girlfriend Jill is in town and has been lying to him for months.
Holly decides that dating a cute guy--who also happens to be Gary's boss--will be a great opportunity to make Vince jealous. But Gary worries that Holly's scheme may cost him his job.
When Vince's grandfather dies, Holly travels upstate to comfort him--then misinterprets his reaction to her thoughtfulness. Meanwhile, after Val's former boyfriend, Rick, has a near-death experience that gives him a deeper appreciation of life.
After skipping her admissions interview at Columbia University in order to spend time with Vince, Holly is shocked to learn that the next available interview is not for another year.
After Henry puts aside his own responsibilities to help Holly with her application for an internship in Paris, she begins to wonder if she made the right decision to end their relationship.
When Holly receives $2,000 from her grandmother for her 18th birthday, she decides to spend it all on a lavish hotel suite. Once again, Val becomes upset with Holly's lack of priorities and vows to teach her a lesson in responsibility.
Exasperated with all of the pre-prom fuss, her conflicting feelings towards Vince and Henry and her impending internship in Paris, Holly decides to host a stress-free "anti-prom" at the loft.
Holly is elated to be 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.
