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.
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 (recurring guest star DAVID de LAUTOUR) 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. In the meantime, Val meets a
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.
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 gets jealous over phone numbers in Vinces' phone. Meanwhile, in an attempt to convince herself that she doesn't have feelings for Vic, Val goes on a date. The guy turns out to be kind of nutty. Gary and Tina try to avoid the fact that they kissed. Lauren tries to find her laptop to talk to her poker guy.
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.
Holly tries to convince Vince to shave his face and they get in a fight over her trying to change him. Meanwhile, Val must figure out if she wants to stay married to Vic. Vic calls his lawyer, and Lauren destroys the annulment papers. Lauren and Gary fight over being the boss of eachother.
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.