Holly 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.
Holly moves out with Ben after Val refuses to let him stay at the loft. When the two end up at Vince and Gary's apartment, Vince agrees to let them stay, in spite of his jealousy of Holly's new boyfriend.
Holly is so determined to help Ben's music career that she risks their relationship when she uses her schoolbook money to pay for Ben to play at a club where pop star JESSE McCARTNEY is performing.
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.
When she can't find a job to earn money to buy Val's wedding gift, Holly enters a contest to become the new "Herbal Essences Girl." A spiteful Tina enters the same contest after Holly criticizes Tina's feelings for her married boss.
Holly is ready to tell Ben she loves him--until she discovers a secret from his past. Meanwhile, Val and Rick argue over Val's controlling nature, and Rick wonders if she is truly ready to share her living space with him.
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.
Holly and Ben are having a difficult time balancing their professional and personal relationship, so Holly enlists Vince's help with a scheme to solve the dilemma.
Holly and Lauren try to take care of last-minute details to keep Val calm as her wedding day approaches. However, when the dress designer suddenly dies, the girls must try to salvage Val's dress.
Val's wedding day is all in place, including a special musical wedding performance by Gavin DeGraw, but everything takes a surprising turn towards disaster when Holly exposes the truth about Rick's recent rendezvous with his ex-fiancee.
When Val decides that she can't go through with the wedding, Holly convinces her to still have a celebration with a personal serenade by rock singer GAVIN DeGRAW. Meanwhile, Holly and Ben must say good-bye when he leaves for a two-month tour.
Holly'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.
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 partners Ben with a new singer but becomes jealous when the sexy singer is attracted to Vince. Val and Lauren get ready to open the bakery, but not before Lauren decides to make sure they get a good review from a local food critic.
After Holly calls out Vince's name while kissing Ben, he breaks up with her on Valentine's Day. Meanwhile, Gary plays Cupid by telling Vince about the breakup, sending Vince running to Holly.
Holly tries to find a way to have a professional relationship with Ben now that their personal relationship has ended. However, Holly may regret her decision when he writes a song about what a horrible person she is.
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.
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.
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.
After recommending to Tina that she get a job where Holly works, Holly confronts Tina when she uses her body, not her brains, to get ahead. Meanwhile, Val argues with Lauren when she uses a customer's death to meet the deceased man's handsome sons.
When her friends accuse Holly of working too much and not having fun, she devises a prank that has Ben believing he is going to be deported back to England unless he marries Holly.
Holly plans a romantic surprise party for Vince's birthday. But havoc erupts when he arrives with a date, and Vince tries to get Holly to admit that she can't make a commitment.
Holly calls a radio psychologist to ask about her relationship problems. The psychologist tells her to talk to her past boyfriends. Lauren breaks a pipe and calls Todd. Holly goes to see Henry at Princeton for help because she does not want to talk to Vince. Vince heard the psychologist talking to Holly and thinks she is going to come and see him.
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.
