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.

When Dave notices how nice Hillary has been to him recently, he is certain it's because she's having sex with someone. However, Mike spies on her and confirms that Dave is actually wrong. Dave then comes to the conclusion that she's smoking his pot when he notices his stash has gone missing. As he's confronting her about it, though, he accidentally tells her that it's his, but quickly tells her that it's not really his - it belongs to Vicky's mother, Betty, that she uses for medicinal purposes.

Dave isn't happy when Taye's family is invited over for a barbecue by Vicky, and has a hard time getting along with Taye's father, Omar. At the barbecue, Omar mistakes some of Dave's comments as racist, because he's a wealthy, African-American. However, when Vicky insists that he go apologize to him, Dave finds himself having a great time at Omar's country club. When he gets home, though, he finds out that Hillary and Taye are on the verge of breaking up.

When Dave finds out that Hillary is asking Vicky about sex, he plans an unexpected family trip to prevent her from going out on a date on Saturday night. Meanwhile, Kenny can't accept the fact that Larry has a new girlfriend, so he tries to break them up.