Jamie has earned some money testing pills so Brenda agrees to go out with him. But the pills have unexpected side effects. Steve and Katie have had three dates but still haven't had any sex, so Jamie suggests the bad boy approach.
Steve gets in trouble with Katie and plays his trump card: he gives her a tape of love songs he made 15 years earlier that always works. This leads Jamie to steal the tape from Katie's apartment to give it to Brenda.
Jamie accidentally kills a duck while visiting a petting zoo with Brenda. So he comes up with a plan to make her cause the death of an animal as well. Katie forces Steve to take care of a digital baby to prove his responsibility.
Jamie ends up with mink coat after a photo shoot gone awry which Steve gives to Katie for her birthday. The coat has a magic effect on their sex lives, and then turns Jamie into the king of the neighborhood.
Jamie gets a job teaching at a posh boy's school and learns them the ways of Dean Martin. Steve and Katie lose a game of charades to Steve's old roommate, but Steve demands a rematch substituting Katie with Brenda.