Valerie Tyler is a 28-year-old organization freak who loves her 16-year-old sister Holly. Even if Holly is rambunctious. Spontaneous. Impulsive. Disconcerting. And definitely disorganized. Then Holly moves in with Val, and the sisters discover they may make better siblings than roomies.
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 has hidden out in the back of Vince's car as he travels to Florida to tell him she loves him, but is heartbroken when she realizes she may have lost him forever.
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.
Holly and Vince have their first fight when Vince takes Gary to a basketball game instead of her. Holly feels that she and Vince should attend sporting events, plays and other events together, though she quickly realizes this idea may not be for the best. Vic still refuses to sign the annulment papers, but it seems that his persistence may be winning Val over.
Holly is sworn to secrecy when Tina confides that she may have feelings for Gary. Likewise, Vince is sworn to secrecy when Gary confides that he may have feelings for Tina. When Holly tells Tina's secret to Vince, it causes trouble between the "friendly foursome." Meanwhile, Vic convinces Val to go on a double date with Lauren and one of his fireman buddies, causing Val to see Vic in a new light.
In Part 1 of a two-part episode, Jason Priestley plays a man who asks Val on a date, which she sees as a perfect way to distance herself from Vic; and Holly and Vince have a fight over jealousy.
When Holly feels that she is ready to take her relationship to the next level with Vince, she is determined to make Vince feel the same. Meanwhile, Charlie proposes to Val, who doesn't want to tell him that Vic is actually her husband. When Vic feels like the 'monkey in the middle,' he decides that he and Val should take a break from each other. Then Val realizes she really does need Vic.
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.
It's Jazz Night at the bakery and Val finally asks Vic to be her date to the party. Though he initially agrees to the date, things go awry when he shows up with annulment papers, but the signing is delayed when Lauren spills champagne on the papers. Meanwhile, Holly persuades Vince to shave his beard by threatening to not shave her legs.
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.
When Vince discovers that Holly makes more money than he does, this causes Holly to update his resume a little bit and give him jobs he never had. Val misses her first date with Vic after a falling-out with Lauren.
Vic returns home after being maimed in a fire, and Val looks at him in a new light; Holly intervenes when it appears Vince's old girlfriend is looking to get him back when he starts work at her real estate firm.
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.
When Val meets Vic's mom Eileen for the first time, she does her best to impress her. In doing so, Val unknowingly causes her mother-in-law to fall off the wagon. Meanwhile, Holly's jealousy over Vince's new partnership with his co-worker causes them to re-evaluate their relationship.
Val runs afoul of Vic's firefighting pals when she withdraws the bakery's offer of providing them with free food and coffee; Tina and Gary try to patch things up between Holly and Vince.
Val panics when she learns that she and Vic were not legally married. Required to wait 24 hours by City Hall before they are allowed to have a civil ceremony, they decide to take a compatibility test, resulting in a fight about how many kids each of them want to eventually have. Meanwhile, Holly is worried she broke up with Vince too quickly, but having spent time at Vic's family reunion, she realizes she did the right thing.
Lauren keeps Holly company when Val and Vic crave alone time. Vince takes Gary's advice on how to get back with Holly.
Lauren hosts a spa day for bride-to-be Val to keep her from panicking when she learns about the Star Wars themed wedding that was accidentally planned for her and Vic. But things go awry when there is a lock-down at the spa.
In the series finale, Valerie finally has her dream wedding to Vic, but there are a few problems. Val, Holly, and Lauren are stuck at a spa where an escaped convict is being searched for, making the three of them late for the wedding.