When her father accepts a promotion overseas in Japan , high-spirited 16-year-old Holly has no plans to head to Japan with him. She decides she'd rather live in the New York City with her "straight-laced" sister, Valerie. In the opener, Holly's attempts to prove herself a perfect roommate backfire when she misinterprets a remark about Feng Shui and rearranges the apartment. To make matters worse, Holly jeopardizes Val's job with a marketing firm when she disrupts a promotional event featuring skateboarder Tony Hawk.

Holly and Val plan a day of at the spa, but Holly finds herself in a 'muddy' situation when she sneaks out of the spa without Val's knowledge in order to meet J.C. Chasez from *NSYNC. Holly must somehow get back inside after being denied re-entry by a security guard. Being Holly, you know she always finds a sneaky way to do things, so she climbs in through a window landing in a mud bath with a naked lady! Meanwhile, Jeff and Gary have an afternoon of male competition after Gary calls Jeff old.

Val has trouble adjusting to Holly's care-free attitude, so she makes her follow a strict set of rules. Holly does her best to follow them, and realizes that she just can't do it. This leads Holly and Val ti the conclusion that Holly is nothing like Val, which is why it is hard for Holly to adjust to the rules that Val has carefully thought of and made up. So Val and Holly question why they ever became roommates.

Gary feels left out when an old female friend comes to visit Holly, but Holly gets a surprise when she catches the pair making out. Meanwhile, Jeff is bummed when he discovers that Valerie still sleeps in an ex-boyfriend's sweat shirt.

When Holly learns that Henry has already lost his virginity she is shocked. She and Tina go and search the city frantically for the girl that 'soiled' Henry. Meanwhile, Lauren tries to get Val to relax and take a day off from work by faking her birthday.

Holly and Tina plan a girls' night out while Henry and Gary plan a boys' night out. Vince sees Holly and Tina at the diner and hooks them up with free front row tickets to The Strokes' concert. Henry tells Holly that he has tickets to The Strokes, but they have a partially obstructed view. Holly wants to tell Henry how she got her tickets, but he says he stood in line for 12 hours waiting for his tickets. Meanwhile, when Val finds out that Peter is number 2 on the "New York's 10 Most Eligible Bachelors" list. Lauren sets Val and Peter up by forging a letter requesting tickets to the party.

When Holly and Tina don't have dates to the prom, they are upset, so they decide to throw an Anti-Prom, with no decorations, no dresses, and no prom king or prom queen. Everyone who doesn't have a date shows up, but when Henry comes with Kate, Holly is heartbroken. Meanwhile, Val doesn't know what to do when she gets an invitation to Rick and Julie's wedding. She tries to look at the post mark to see if it was sent before Julie's "no contact" rule, but the postmark is smudged.