Widower Doug Simpson (Danza) is a radio producer from California who lives with his two daughters, Bonnie and Katie (Dolenz). When his oldest daughter, Katie, turns 15, she feels it's time to start looking more grown-up after years of having an unflattering wardrobe that includes thick glasses and full set of braces. When Doug leaves on a business trip, Katie transforms herself into a knockout beauty with help from her father's girlfriend Janet Pearson (Hicks). When Doug returns, he is shocked to find boys from every walk of life interested in dating Katie, with Katie having up to three boyfriends.
This film contains examples of:
- Bigger on the Inside: For his prom's after-party, Timothy (Matthew Perry) somehow manages to find the only motel in California that offers full suites with private bedrooms.
- Boyfriend-Blocking Dad: Doug is a textbook example of this. Roger Ebert condemned the film for dragging this into Squick levels.
- Braces of Orthodontic Overkill: Downplayed. Pre-makeover Katie had a full set of braces that, while not the usual humongous device that sticks out of people's mouths, are still portrayed as very unwieldy and awkward.
- First Girl Wins: Gender-flipped. At the end of the film, Katie reunites with Richard, the boy next door whom she's been dating since middle school.
- Good Stepmother: Katie's father's girlfriend Janet, who helps Katie with her makeover out of pure niceness.
- Here We Go Again!: At the end of the film, Katie's younger sister Bonnie, who up until then was a straight tomboy (whereas Katie was simply Hollywood Homely), begins her own dating spree.
- Nerd Glasses: Katie's unflattering wardrobe pre-makeover includes a thick pair of these.
- She Is All Grown Up: Basically the whole premise of the movie; when dowdy Katie gets a makeover while her father is out of town, he returns to be shocked and horrified that Katie is now being chased by practically every teenaged boy.
- Songs of Solace: Katie locks herself in her room playing her music at full volume after a fight with her father and a breakup with her boyfriend. When one of her friends comes looking for her, she is directed "up the stairs, follow the sad music".
- Tomboy and Girly Girl: Bonnie is a tomboy, while Katie, despite her unflattering clothes, is still the more feminine one.