16-year-old Hillary's father, Dave, refuses to let her go out on a date with a guy older than her. So, to deceive him, she brings a new ""study buddy"" over to the house instead. At the same time, Dave and Vicky are having trouble trying to figure out how to understand their son, Larry.

Vicky decides to turn to an old, ex-boyfriend over the internet for advice about what to about her son, Larry, who insists on wearing women's clothes. While she's online, though, she discovers some of Dave's secret e-mails he's been sending to someone with the screenname ""Lonely Lady in Michigan."" Having discovered this, she decides to confront him. However, Hillary also has some problems of her own, but refuses to to tell Vicky about it.

Dave becomes upset with Larry because of his lack of interest in masculine activities, and his lead role in the ""Annie Get Your Gun"" play at his high school. Things get worse for Larry when his parents see him kissing what they think is a guy, which convinces them that Larry is, in fact, gay. Meanwhile, Hillary has to deal with her new image at school after she hits another girl and gets dumped by Taye.