The movie begins with Eugene (Slade Pearce) and his best friend Tucker (Remy Thorne) as kids. They sneak into the bedroom closet of Eugene's brother, as he recently acquired a valuable Michael Jordan rookie card. Upon opening the box the card was in, Tucker notices that Eugene's brother has an issue of Playboy. Tucker opens the magazine, instantly becoming obsessed with it. Three weeks later, Tucker's demeanor has changed to that of a hormone driven teenager, despite that he is only 8 years old. Fast forward ten years later, Eugene (Zach Cregger) and Tucker (Trevor Moore) are seniors in high school.Tucker is still a huge fan of the Playboy franchise, while Eugene and his girlfriend of two years, Cindi Whitehall (Raquel Alessi) are public speakers on the subject of abstinence for younger teens. Despite this, in reality, Cindi has other plans, stating that since they have been together for two years, if she is not Eugene's first then they have big problems.They decide to go through with it at the after prom party that Tucker had invited them to. On the day of prom, Tucker tells Eugene that he has the limo booked, which when pulls up, has already picked up Tucker's high school drop-out friend, Phil, who now goes by the MC name of Horsedick MPEG (Craig Robinson). At the After Prom party, Cindi goes upstairs to prepare, while Tucker takes Eugene into the kitchen and gives him several shots of hard alcohol. As Eugene leaves to go upstairs to meet Cindi, he walks through the wrong door, and falls down the steps into the basement. He is hurt so bad, that he falls into a coma for four years.After Tucker wakes Eugene with a baseball bat, he tells him that Cindi stuck around for a little while, but disappeared shortly thereafter because Eugene was "a vegetable." Tucker left Eugene to continue his recovery as Tucker went to work. He came back later to visit Eugene again with the newest edition of Playboy. While discussing where Cindi had vanished to, Tucker happened to stumble across a centerfold in his new issue of none other than Cindi. Tucker devises a plan to go cross country to the Playboy Mansion where there was a party to be held in 3 days for Playboy's annual Birthday bash, where Cindi was sure to be. Tucker left as he had a date with his "partner" of 13 months, Candace (Molly Stanton), who back in high school seemed to hate Tucker.Later that night, Tucker broke into the hospital while Eugene was asleep, stating they had to leave on their trip now, as opposed to 3 days later, as Tucker had an incident involving Candace and accidentally forgetting she has seizures caused by strobe lights as a side effect of her epilepsy. Starting out on the road trip, the two are attacked by Candace's brother, Rick (Geoff Meed), and his firemen crew, but manage to escape temporarily.Once in Chicago, they meet up with their old friend MPEG, who has become a famous rapper over the four years. They all hop on board his party bus and begin to trek across the country towards the Playboy Mansion. After an argument between Horsedick and Eugene, Tucker and Eugene were both thrown out of the bus in the middle of nowhere, and left to walk the rest of the way. Just as it seemed all hope was lost, a car pulled up with two lesbian women. They make a deal where the boys will drive while the girls are in the back with each other having sex.They make it all the way to the Mansion only to be stopped by bouncers at the door. Moments later, several fire trucks arrived, in search of Tucker. Tucker and Eugene manage to sneak into the mansion dressed in fireman outfits. The two go in separate directions while outside, Candace forces her way into the mansion, followed up by her brother, Rick. Tucker randomly hits on several Playboy models and meets PMOY 2007 Sara Jean Underwood and makes his way to the Grotto. Eugene, in search for Cindi, is suspected of being a stalker and is taken into a secure holding area, but not before being spotted by Cindi.Meanwhile, Tucker runs into Candace and darts back into the mansion, where he is spotted by the firemen. After avoiding the firemen, he tries to hide in the mansion and suddenly finds himself face to face with Hugh Hefner. Hugh and Tucker have a discussion about Tucker's issues, telling Tucker about the first woman he ever fell in love with. Hefner tells Tucker that "there is a bunny in every woman," and that if Tucker can only see the "bunny" in those women, that he's on to something.Back in the holding area, Cindi comes in to see Eugene. Eugene seems disgusted to see her, claiming that she left him behind and didn't care about him, and accusing her of sleeping with countless other men. Cindi argues that she did still love him and proves it by telling Eugene that the money she made modeling and being a Playboy Bunny was sent to help pay for Eugene's hospital bills, something Tucker never bothered to mention due to his absent minded nature. Just at that moment, Hef had called to have all stalkers removed from the mansion. Once tossed out on the streets, Candace finally caught up with Tucker. Tucker apologized for his faults and promised to look past hers and Candace decides to give him another chance. At the same token, Eugene runs into Horsedick.MPEG, who promised to "rip Eugene's face off." Eugene seems too distracted regardless to find Cindi. After Cindi comes out and reveals that MPEG was born without genitals, his crew pull down his pants, showing a straw sticking out where his genitals should be, confirming what Cindi said. MPEG leaves ashamed, and after Eugene and Cindi make up, Hef lets everyone back in.Eugene and Tucker find themselves in the Mansion's kitchen, and Eugene tells Tucker that Cindi is waiting upstairs for him, shades of the situation that started the whole mess in the first place. And just like 4 years previous, Tucker and Eugene take several shots together before Eugene goes upstairs, where he finally has sex with Cindi