Kevin tells Jamie he's marrying Sarah and moving to Chicago. At first Jamie tries an intervention, but then begins to think that it may be time for him to grow up as well.
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.
Brenda and Katie have a falling out, leading Jamie to become Brenda's new best friend and Steve having to introduce Katie to his made-up 'Uncle George'.
Jamie becomes an overnight sensation as a maternity nurse who specializes in speedy births. Meanwhile Steve and Katie are busy spying on the new neighbor and her two lovers.
Steve manages to avoid having to visit Katie's family for Christmas but soon feels bad about it. Jamie wants to win the local Kareoke contest so he can buy Brenda a big present.
Jamie has to find either a new roommate or a new job after Kevin's marriage. Enter Steve, who is looking to get out of his relationship and soon falls for Brenda's new neighbor Katie.
Katie has gone back to her natural brunette hair color. Steve is afraid to tell her he prefers her as a redhead. Jamie is dating a female semi -pro basketball player almost twice his size.
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.
Steve tells Jamie he has to contribute to the house expenses and puts him in charge of a task at his office. Katie and Brenda try to catch the elusive maintenance man Bob.
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.