Inside Drew's house, he's getting some food from the fridge when he goes outside, where Lewis, Oswald and Kate are half-naked, playing pool, in the middle of winter. They are using heat lamps to heat up the area, but then the heat lamps die, they go inside to get warm. There's then a knock at the door, it's Drew's older brother, Steve, disguised as a pizza delivery man. Steve reveals a lot of things haven't been going so well, and he asks if he can stay with Drew for a while.
Drew and Steve come into Drew's house and talk about Drew's old girlfriend, which impresses Steve. Lewis and Oswald come in and help move Steve's suitcases in. Steve asks about a job, so Oswald tells him about an opening at Global Parcel, but he doesn't quite seem interested. Steve asks Drew if he can help him get a job at Winfred Louder, possibly at the make-up counter, so he can keep an eye on Kate so she doesn't get in any trouble.
At work, Kate complains to Drew, who stopped and helped a donut truck that broke down. Mimi comes in wearing a scarf, covering her face, since she had an allergic reaction, and cannot wear make-up for some time. Mr. Wick comes out and tells her that she has to remove the scarf tomorrow when she comes to work. Drew asks Mr. Wick if, as a joke, he would go and fire his brother, and he agrees to do it.
Downstairs, Steve, dressed as a woman, is helping a woman with applying make-up when Drew comes down, looking for his brother. When he realizes "Stephanie" is actually his brother, Steve, he freaks out. What makes it even worse is when Mr. Wick comes down and seems to find "Stephanie" attractive, and is a little red in the face when he is told who "she" really is.
In Oswald's delivery truck, he's giving Steve and Kate a ride home. Oswald can't help but ask Steve what's with the dress, so he says he's a cross dresser, and wonders if Drew went straight home. Oswald can't help but ask Steve questions about why he cross dresses.
At the Warsaw, Drew's having beer with Nicki and Lewis. Drew just can't get over what Steve was doing. Steve comes in and wants to talk to Drew. Nicki and Lewis walk over to the bar, to let Drew and Steve talk alone. Steve tells Drew that he has to dress as a woman for work, as it gives him confidence. He apologizes about putting him in a tough spot, since Mr. Wick wants Drew to fire him.
At work, Mimi comes walking in, with a small paper fan in front of her face. Nicki comes in to tell Drew that everyone's ready. Drew calls out Mr. Wick and insists he wants his brother to stay on, but Mr. Wick insists he fire him. Drew decides to play a little game with Mr. Wick: Steve can keep a job if Mr. Wick isn't able to tell the difference between a man and a woman in a lineup. If Mr. Wick wins, he gets Drew's pool table, the one that was not only his, but his father's.
Still at work, Drew and Nicki are showing Mr. Wick around downstairs and tells him to find the man amongst all of the women. Mr. Wick confesses he can't find the man in the group.
At home, Drew and Steve are playing pool. They talk about how their dad doesn't know about Steve's cross dressing. Just as Lewis is coming outside, Steve quickly tells Drew to keep a straight face. It seems that Steve applied a bunch of make-up on Lewis while he was sleeping on the couch. Lewis says he's leaving on a date, he's even meeting the girl's parents tonight.
The show ends with Oswald giving Lewis a ride to his date's house. He's somehow able to keep a straight face through the whole thing.