The episode begins at the bar with the gang talking about Penny’s breakup. Penny is presently living with Brad and Jane for some moral support, and they all joke how they are like a mom and dad to Penny. Jane feels Penny should begin dating other guys, but Penny isn’t so sure. Jane isn’t ready to take no for an answer, and she plans a double-date at her house. During the conversation the check arrives, and Max, who is completely broke, says dinner is on him and runs to the door, after telling the rest of the gang to do the same.
He sees none of them is ready to comply, so he returns and tells them about his money problems. Dave urges him to get a job, but Max says he doesn’t have the money to even go for an interview, so Alex lends him some. At Jane’s office, Brad arrives to pick her up, she isn’t in, but he sees Car Czar looking around in her office for a Luna Bar because he needs a shot of estrogen to get rid of the hair on his back. Brad asks how his wife is and he says she kicked him out and is slapping him with a divorce. He seems really depressed, so Brad is forced to invite him for the dinner, he and Jane are hosting at home. Jane comes in and isn’t too pleased on learning, what Brad has done, but she pretends otherwise.
At Dave and Alex’s, they enter and find Max sitting on the couch. He tells the duo that he has decided to do something better than get a job. He has signed up for the “Chicago Super Gay” pageant the winner of which gets a $1000 prize. Dave and Alex both agree that it’s a great idea and even volunteer to train Max for the event. At Brad and Jane’s, during dinner, the Car Czar manages to really offend Sean, who Jane was trying to hook up with Penny, so he walks out. Penny is really mad and storms off to her room in a huff, after reprimanding the Car Czar for his behavior. The next day, at Alex and Dave’s, after Max has woken the duo, he tells them the competition will be stiff, so they need to begin the training. He informs the duo the category each of them will be training him in.
At Brad and Jane’s, the duo is shocked on learning Penny slept with the Car Czar. Penny admits she made a “boo boo” and wants the duo to fix it. At work, Jane talks the Car Czar out of dating Penny by telling him that Penny is a democrat, but when she returns home, she sees that Penny has again ended up sleeping with him. Penny apologizes to her, saying she just can’t resist the Car Czar, who she feels is like a balding “Don Draper” and is amazing in bed. Alex and Dave are both busy training Max, who seems a bit overwhelmed by the things he is being asked to do by them.
While Brad, Jane and Penny are having lunch and the duo is trying to talk Penny out of sleeping with the Car Czar, the man himself arrives. Penny, who simply can’t get enough of the car Czar sexually, is all over him, while he feeds her some whipped cream with his fingers. On seeing this, Brad and Jane can barely stop themselves from puking. At the pageant, Max isn’t really doing a great job of either impressing the audiences or the judges. To make matters worse, Alex and Dave are prompting him to do things the way each of them wants, which is confusing him further. At Brad and Jane’s, the duo is finding it nearly impossible to filter out the sounds of Penny and the Car Czar having sex in the guest bedroom.
At the pageant, Max fires both Alex and Dave, saying he wanted their help, but they turned it into a competition against each other. At Brad and Jane’s, after Penny sees off the Car Czar and closes the door behind her, Jane and Brad confront her, saying she is forbidden from seeing the Car Czar from now on. Penny refuses to comply, saying they are not the boss of her and just to agitate them, she even claims that she loves the Car Czar, which when he enters. He says he came back to get his keys and adds how touched he is to hear her say that she loves him. He says he loves her too and hugs her, while Penny, who was making the whole thing up, knows she is in trouble.
Next, the Car Czar moves into Penny’s house, while she looks on silently. At Max’s, Dave and Alex apologize to him for their earlier behavior and tell him that they have come up with a “kick ass” routine to help him win the pageant. At Penny’s, the Car Czar gets a call from him wife, telling him she is ready to take him back. Penny pretends she is heartbroken and breathes huge sigh of relief after seeing him off. Jane and she then have a chat. Jane apologizes to her and even admits that she is the one, who convinced the Car Czar’s wife to take him back. Penny in turns says she did need a fling and because the Car Czar was a pig, she luckily didn’t get emotionally involved. She adds that she doesn’t even know the Car Czar’s actual name.
After Jane tells her it’s Lorne, Penny in dismay comments that she can’t believe she had sex with a Lorne. At the pageant, the audiences, the judges and even the host loves the act Dave and Alex have cooked up for Max. Max wins the pageant. Later at the bar, he thanks the gang for their support. The Car Czar is also sitting with them because Brad simply can’t stop himself from inviting him wherever they are. The episode ends.