Jennifer, portrayed by Alicia Silverstone, takes on a babysitting job for Harry Tucker (J.T. Walsh) and his wife, Dolly (Lee Garlington). While the couple enjoys a night out, indulging in drinks, Harry finds himself daydreaming about the attractive babysitter. Meanwhile, Jennifer's boyfriend, Jack (Jeremy London), and Mark (Nicky Katt), another suitor, hatch a plan to secretly observe her at the Tuckers' home, each captivated by her charm. As the night unfolds, tensions rise, leading to unexpected and humorous scenarios.