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 on. When Holly goes to Vince's, she finds something she wasn't expecting. Meanwhile, Val and Lauren run into Rick (Val's ex-boyfriend) while they are at the diner. They make lunch plans, and reminisce on old times.

Holly and Vince try to be friends again by throwing a surprise birthday party for Gary's 18th birthday. When Holly and Vince run into Jill (Gary's ex-girlfriend) at the diner, who is supposed to be in Paris. They find out that for six months, Jill was really in New York! Holly and Vince argue whether or not to tell Gary about Jill - especially on his birthday. Meanwhile, Rick and Val keep visiting each other, and Lauren keeps bragging about her new boyfriend-who is a doctor!

Holly is puzzled by Vince's recent antagonistic behavior toward her until she learns the truth about why he was so brusque with her. And Val tries to sort out her feelings toward Rick.

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 thought they were. Meanwhile, while writing her college report, Holly forgets to save it, and it gets deleted! She asks Henry for help, and he does, which causes him to not meet his idol Bill Joy and receive $10,000 in cash. Holly questions the breakup between her and Henry.

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 the time has come to decide between them. In order to distract her from Rick's upcoming wedding, Val books a trip to Venice with Lauren, but when Val gets sick and has to cancel, she is pleasantly surprised when a still-single Rick shows up at her doorstep. Meanwhile, it could be a summer of love for Gary and Tina when they have their second kiss.

Holly returns home from Paris with Ben, a handsome British musician who has stolen Holly's heart.Vince and Henry Realizes they've losted Holly, Henry says goodbye to Holly one last time before leaving for Princeton. Meanwhile, Val, who has spent the summer with Rick, receives a surprise proposal after she reveals her own surprise.

Holly moves out of the loft with Ben when Val tell her that Ben can not live in the loft with them. Holly and Ben then end up at Vince and Gary's apartment, Vince agrees to let them stay there, Meanwhile, Val is concerned her fear of commitment is affecting Holly and wonders if she did the right thing by breaking off her engagement with Rick

Holly works so hard to try to help Ben's music career, that she risks their relationship when she uses her money for school books to pay for Ben to perform at a club, where pop star Jesse McCartney is performing. Meanwhile, Rick asks Lauren to help him shop for the a ring for Val , Lauren chooses the perfect ring but she chooses for herself.

Holy moves up Vals Bachelorette party, because Ben has a gig the same night, Val gets upset and bumps Holly from the position of Maid of Honor, leaving Lauren to be the Maid of Honor.

Holly discovers that she loves Ben and that she wants to tell him, but she doesn't want to tell him that his new song is horrible, so she takes Lauren's advice and lies to him. All seems fine until Holly finds out that Ben wants to send his song to a producer. Holly then admits that she doesn't like Ben's song and Ben becomes upset with her: not because she hated his song but because she lied to him. Meanwhile, Val and Rick argue because she is having trouble adjusting to Rick's lifestyle.

Holly starts feeling jealous of some of Ben's fans, so she tries to make Ben jealous in return. But when Holly's plan does not work Vince steps in with an idea of his own. Also Rick's mother is coming to visit, and Val wants her soon-to-be mother in law to like her, so she goes crazy trying to get everything just right.

Val is acting very anxious because her wedding is coming up soon. She becomes even more anxious when she finds out that her dressmaker, Gittle has died and that her wedding dress has been given to a thrift store. Holly, Vince, Gary, and Ben go to the store to get the dress back but to their disappointment, the cashier just sold it. Meanwhile, Holly, Ben, and Gary see Rick having pizza with his ex-fiancee, Julie at the pizzeria next door to the thrift shop, when he told Val that he was in New Jersey on business.

The wedding is almost here, and everyone is nervous. Ben gets a contract to go on tour, and Holly has the opportunity to go with him. Vince is furious. Tina is going out with her married boss (or so she thinks). She goes to Vince's afterward and they end up sleeping together. Holly doesn't know whether to tell Val of Rick's meeting with his ex. She tells Val, but makes it clear that his ex (Julie) was the one who called him. Julie tells Holly that Rick called her. Holly gets to the wedding just in time to walk Val down the aisle. As they are walking down the aisle, Holly tells Val that Rick called Julie. See you after winter sweeps for the conclusion of this episode...!

When Val comes to the conclusion that she can't go through with the wedding, she takes her anger out on Holly. Meanwhile Holly was thinking she would not go on tour with Ben, because Val needs her, but because Val is mad at her she decides to go. On her way to the train, Holly realizes why Val was angry, and decides that she can't go with Ben. Also Gary finds out Vince and Tina slept together.

When Val and Vic's annulment papers come on Thanksgiving, Holly gives them to Tina to get rid of, so it doesn't ruin Val's Thanksgiving like last year. Meanwhile, Lauren and her online poker buddy decide to meet each other for a date, and they both get the shock of their life.