Jeff suggests that Val should be more spontaneous and impulsive, but his advice backfires when Val who is dressed like a sexy cheerleader, is caught by Jeff's mom who has unexpectedly come to town. Meanwhile, Holly and Gary are at odds over a free "iBop" that Gary insists belongs to him.

Holly volunteers to fill in at Val's office over spring break, but the girls clash over the tactics Val should use to land a promotion over a competitive colleague; Holly believes in playing dirty and kissing up to the boss and Val thinks her hard work and dedication will get her noticed.

When Henry is away at Princeton, Holly realizes that she loves him, and will go at any length to tell him in person. But things go wrong when Holly takes a train to Princeton, and Henry takes the train to Holly's house. Meanwhile on a business trip, Val winds up getting the hotel room next door to Peter's, and they wind up kissing.

When Henry's parents kick him out, he moves in with Vince, making Holly feel awkward. Meanwhile, when Lauren realizes that Val hasn't had a boyfriend in a while, she sets her up by speed dating. Val meets a guy she really likes, and they plan to go out on a date. But things go wrong when he doesn't show up, and nobody can find him.

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!

When Holly and Tina are shopping at F&A (Gary's new workplace), Holly meets Greg, Gary's manager. Greg asks Holly out on a date, and she accepts, just to make Vince jealous. Everyone decides that they're going to Holly's house to see a lunar eclipse, and that's when everyone's true feelings come out.

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.

When Holly enters a contest to become the new "Herbal Essences Girl" to earn money for Val's wedding gift, Tina, who is mad at Holly, enters against her. Val finds a love letter Rick has kept from his ex-fiancé, and gets worried.

The group celebrate Halloween, by going to a party at the diner where Holly and Ben dress up as Sonny & Cher, Gary and Danielle as Ike & Tina Turner and Tina and Vince as Homer Simpson and Jessica Simpson. Everyone is shocked when they find out Holly dropped out of college. Meanwhile, in order to get Val to relax, Lauren takes her to a 'dude ranch' that turns out to be a nude ranch.

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.

Holly wants Ben to yell at her for breaking his heart and when he doesn't, she gets upset with him. Finally, he writes a nasty song about her and wants to sing it during his performance at the club. Elsewhere, Val allows Lauren and Gary to watch the Sugar Baby Bakery while she goes out to lunch with Holly and they get robbed...By a 10 year old.

With Holly and Vince now an official couple, Holly is determined to make her relationship work even though they must spend a few months apart while Vince is in Florida. Meanwhile, Val and Lauren devise a plan to force Val's new husband Vic out of her apartment so they can end their "quickie" marriage.

When Holly and Val's father Jack drops in for a visit, the girls do their best to impress him. However, during a nice dinner, Holly and Val accidentally catch their father in a compromising position with his business partner. With all the Tyler family secrets out in the open, the group enjoys a nice evening 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.

Lauren lies about a surprise party for Valerie so she can see Rick, but the truth comes out when the affair lands Rick in the hospital, and Val cannot forgive her friend for the deceit. Meanwhile, Vic has a special gift for Val, but has trouble finding the perfect time to give it to her.