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1-86 of 86
- 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 and Vince have their first fight when Vince takes Gary to a basketball game instead of her. Holly feels that she and Vince should attend sporting events, plays and other events together.
- 2002–200622mTV-PG7.8 (53)TV EpisodeHolly 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.
- 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 determined to heal Ben's broken heart by fixing him up with a sexy singer. When she asks Vince for help, their friendship is renewed. Meanwhile, Val gives a job to a homeless man who becomes the object of Val and Lauren's dueling affections.
- 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.
- When Vic returns from the hospital following his accident, Val waits on him hand and foot and even gives him sponge baths. Meanwhile, Holly gets jealous when Vince spends time with his new co-worker.
- 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.
- Holly's still mad with Tina for having a one-night stand with Vince but she becomes furious when she learns that her own sister had a liaison with Todd the plumber, which caused Val to miss Holly's comedy act at Giggles 10 years ago.
- Ben being more and more busy with work, Holly starts spending more time with Vince. Meanwhile, Lauren tries to find an easy way to tell Valerie that their company went under while she was busy with her wedding plans and subsequent breakup.
- Holly and her friend Henry (MICHAEL McMILLIAN) skip school and "borrow" Val's car, but they panic when the car is discovered missing. Meanwhile, Gary helps Jeff gain a new restaurant management job but expects free food in return.
- In the season finale, Holly is excited to tell Vince she is ready to move forward in their relationship. But Vince, after seeing Holly in the arms of her ex-boyfriend, has had enough and travels to Florida for the summer.
- 2002–200622mTV-PG7.5 (61)TV EpisodeHolly had been torn between Vince, and her former boyfriend, Henry. Luckily, her summer internship in Paris came through, allowing Holly to leave both guys--and all her confusion--behind, at least for the summer.
- Now that Val is truly attracted to her firefighter husband, she eagerly awaits a date they planned. But when she has a big argument with Lauren over Lauren's relationship choices, Val misses the date.
- Holly helps the group get ready to celebrate while holding onto her secret about dropping out of college. Lauren takes Val to a "dude" ranch, but they wind up in a "nude" ranch.
- While Holly and Vince continue to fight for their friends' loyalty, Holly purposely leaves Vince behind when she invites Tina, Gary and Ben on a vacation. However, Vince unexpectedly shows up and comes to Holly's aid when she suffers has food poisoning.
- While Jeff is out of town, Holly takes Val on a night out. However, the female bonding stops when Hunter, a guy Holly wants to date, makes a romantic advance on Val. The situation gets worse when Hunter's jealous girlfriend, Sasha, arrives.
- Holly reschedules Val's bachelorette party to a different night after Ben gets a gig on the same night as the party. Angered by Holly's actions, Val fires her sister as maid of honor, replacing her with Lauren, who is more than willing to step in.
- On Thanksgiving, Holly and Vince discover Lauren kissing Rick, Val's ex-fianceÌ, and they try to hide the truth from Val. However, the situation leads Val to seek comfort from Vic, and the two decide not to sign their annulment papers.
- Holly and Vince go to the country for a romantic weekend, and Holly decides she is ready for the next step in their relationship. Upon learning of Holly's desires, Vince feels immense pressure and has second thoughts.
- When Holly spends all of her money on an expensive sweater, Jeff agrees to hire her as a waitress, Holly's first job. But he regrets his decision when Holly wreaks havoc in the restaurant and even causes the chef to quit.
- 2002–200622mTV-PG6.7 (49)TV EpisodeHolly's excitement about landing a job at a music management firm is cut short when she feels that her new boss doesn't like her. Meanwhile, to help Val forget her troubles, the group takes her to a local club where Val bonds with another woman.
- 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.
- After waking up to find a wedding ring on her finger, Val is surprised to learn that she has married her old boss, Vic, during a wild night in Atlantic City. Meanwhile, Holly is determined to tell Vince that she loves him.
- 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.