Peter, Joe and Quagmire drag Cleveland to a bar to get him to meet some women, as he's still reeling from Loretta having left him. It doesn’t work so well, so when The Bachelorette comes to Quahog, Peter takes Cleveland to try to join. Cleveland gets nervous at the audition and in an effort to calm him, Peter removes Cleveland’s clothes and then his own. The producers see this and Brian apologizes for what happened with Peter and Cleveland. After meeting Brian, they recruit him to be a contestant. He signs up for the free martinis and food, but ends up falling in love with the reality starlet, Brooke. Quagmire and Brian are the final two contestants on The Bachelorette. When Brooke visits the Griffins, it is very catastrophic, but not nearly as bad as the dinner she had with Quagmire and his mom. Brian wins her heart and the final rose, but when the cameras are turned off, Brooke tells Brian that it was nice "working with him", and it is apparent that the show really is scripted, as Brian thought. Brian quickly becomes obsessed with her and leaves several messages on Brooke’s answering machine, even though she never gets back to him. Brooke gets mad at Brian for stalking her. Afterwards, he gets a guitar and sings to Brooke. He finally stops stalking her when she throws the phone at him after he shows up at her apartment, upset that he became the very thing he was mocking in the beginning.
Meanwhile, Chris has a pimple on his face which he names “Doug.” Lois worries about Chris, as Doug tells Chris to make some mischief. He goes to the Swansons' house and sets a bag of feces on fire on their porch, and writes “That’s enough, John Mayer” in spraypaint on the wall of the Quahog Mini-Mart. Lois sees Chris sneaking back into his room and is going to punish him but Chris tells her that Doug said he does not have to listen to her. This outrages Lois, deciding to go to Goldman's Pharmacy the next day and get some astringent to get rid of Doug. However, the next day, as Peter and Lois head to Goldman’s, they realize there has been a break-in, and someone has destroyed Mort’s entire stock of acne medication. That night, when Brooke comes over for dinner to meet Brian’s family, Doug tells Chris to lift up Brooke’s shirt. He does this, shocking and offending the family. Joe comes in, saying he has proof that it was Chris who vandalized, broke into Goldman’s Pharmacy and stole Mort's acne medication. Chris decides he no longer wants to listen to Doug after he made his mom cry, but Doug says he could make Chris punch himself, or even worse, shoot him in the brain. Chris finally winds up at the dermatology clinic, and a struggle ensues as Doug tries to shoot him in the brain, but Chris manages to overpower him and use cortisone on the zit, finally taking it out.