Both Henry and Vince kiss Holly just days before her summer internship in Paris begins. Meanwhile, Valerie keeps a stiff upper lip on Rick's wedding day; and a sick Lauren takes refuge in the Tylers' loft.

Holly throws a party for her classmates who are not going to the prom, but the evening doesn't quite go as planned. Elsewhere, Valerie gets an invitation to Rick's wedding, but she wonders if it was sent to her by mistake.

Holly receives a large sum of money for her 18th birthday and decides to blow it on a big party, ignoring Valerie's advice to put it in the bank. However, the teen's irresponsibility with the cash gives her sister a chance to teach her a lesson

Holly writes an essay that she hopes will win her an internship in Paris, but a computer glitch puts her plan in jeopardy. Meanwhile, Valerie hosts a party for Rick and his fiancée, a woman who learns some surprising things about the man she plans to marry.

Holly postpones a college interview at the last minute so she can hang out with her friends, making Valerie angry since she spent time preparing her sister for the meeting. Elsewhere, Lauren finally does the deed with her new boyfriend, but it turns out to be a disappointing event.

Holly struggles with her friendship with Vince and ends up offending him at the diner, but she only makes matters worse when she tries to apologize. Elsewhere, Valerie's friend Rick becomes obsessed with trivial things after a near-death experience on an airplane.

Holly dates Gary's boring boss, but when she tries to dump the guy, she sees Vince with another girl, so she prolongs the relationship to make Vince jealous. Meanwhile, Lauren learns that Valerie has applied for a job, so she quits the Tyler firm.

Gary upsets Holly when he says that he wants to take Vince's advice and celebrate his birthday at a club rather than at their usual skating-rink outing. When Holly confronts Vince about his meddling, she runs into Gary's ex-girlfriend, who's supposed to be in France.

Holly's ready to date Vince after seeing Henry with a new girl, but her plans are derailed when she finds Vince with someone else. Elsewhere, Gary gets a new job at a store that requires him to work shirtless, much to the delight of female customers.

Vince is injured while delivering a package and ends up in the hospital, where he kisses Holly for the first time when she comes to visit; Valerie and Lauren compete for the attention of a cute doctor.

Holly asks Gary to trick Henry into meeting with her, but the plan backfires and strains the bonds of friendship among all of them. Elsewhere, Valerie swears off sugar and tries to persuade Lauren to join her.

After they have a fight, Holly goes looking for Henry, who overheard a conversation that revealed one of her secrets.

After a fight with his dad, Henry moves in with Vince, an arrangement that Holly finds troubling as she frets over her attraction to Vince. Meanwhile, Lauren persuades Valerie to try a speed-dating service.

Holly examines her feelings for Henry after he goes on a weekend visit to Princeton; and Gary awaits his girlfriend's return from France. Elsewhere, Valerie takes a business trip to Chicago and runs into Peter, who's there with a female companion.

Holly lies to Henry about how she got front-row seats to a concert because she doesn't want him to know that Vince was with her at the time. Meanwhile, Valerie goes to a bachelor event honoring Peter and other eligible men.

Holly and her friends try to get Tina to apologize to her boyfriend for insulting him, in hopes of salvaging a planned ski weekend. Elsewhere, Lauren turns to Valerie for help with landing a new man.

Valerie finds Holly in a compromising position with Vince on their apartment terrace on a night when Henry is studying with friends. Elsewhere, Valerie keeps running into her former boss at a local gym.

Holly learns that Henry had sex while in a previous relationship, so she and Tina set out to meet his old flame. Meanwhile, Lauren persuades Valerie to spend a workday relaxing at the loft and spices things up by hiring a pair of masseurs.

Holly tries to persuade a rich, incarcerated man to let her and Valerie move into his loft so that Valerie can have her own office.

Valerie tries to land a client by getting Holly to befriend the client's teenage daughter, but their plan goes awry when Holly tries to take the fall for the daughter's reckless behavior.

Valerie feels slighted by her boss when he gives a new client whom she recruited to a pair of male co-workers. Meanwhile, Holly upsets Henry when she leaves the dentist's office during his surgery to help Valerie out of a jam.

Holly tells Henry that she loves him, a slip of the tongue that strains their relationship. Elsewhere, Valerie accepts a date with her new boss.