Twelve-year-old Annie Lamm's first day of summer break quickly turns into a disaster. She realizes that her parents have not only decided to fly her to Hilton Head Island during their second honeymoon, but they also plan to coerce her to spend half her summer with her 76-year-old Grandpa Donald whom she hardly even knows.

At the Tanglefoot Children's Camp in North Carolina, kids learn to get along with each other and to gain self-confidence under the friendly counsel of camp director Gregg.

Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother was right about how misguided she was -- and falls for him.

Ambitious stage mother Rose wants desperately for her daughter, June, to become the vaudeville star she never was. With the help of savvy but kind-hearted agent Herbie, Rose realizes her aspirations for June, but when her star rebelliously elopes, June's shy sister, Louise, reluctantly steps into the spotlight, transforming herself into the legendary burlesque star Gypsy Rose Lee.