Larry reveals to his parents that he suffers from Social Anxiety Disorder, so Dave and Vicky try to put him on medication, but Larry refuses and accuses them of wanting to change who he is. Meanwhile, Dave is convinced that Hillary intends to lose her virginity on prom night, so Vicky ends up giving her the "sex talk."
Due to cutbacks at work, Dave and his two co-workers quit their jobs and start their own business. Meanwhile, Hillary decides to join the Army after not receiving any college acceptance letters, and Larry refuses to get his driver's license.
When Larry wears Dave's jacket to school by mistake, he ends up getting suspended for 30 days by Principal Fink for finding pot in it. This leads to Dave and Vicky trying to get him enrolled in a parochial school with the same priest who Mike thinks is hitting on him.
Dave puts the kids on a strict allowance, since they're always asking him for money. Vicky supports him on this... that is, until she, too, is put on a budget and is unable to buy the Prada boots she's always wanted. Meanwhile, after spending all his allowance money on the first day at Medieval Times, Larry asks Mike to loan him some money. And, in order to earn some extra money, Hillary starts an escort service for the nerdy boys at school.
Dave accuses an incensed Hillary of cheating on her SATs after she gets a surprisingly high score. Meanwhile, Vicky and Dave meet a couple who may be interested in more than friendship, and Dave asks Larry to take a client's daughter out on a date, only to find out that she isn't an ideal match for him.
When Dave and Vicky were growing up, their parents had it easy. Back then, there were no “time-outs,” no one had any “boundaries,” and “parenting” wasn’t even a word. Parents had no idea what their kids were really up to and ignorance truly was bliss. Now Dave and Vicky have teenagers of their own, and anything their kids might even think about doing, Dave and Vicky have already done… at least twice.