The movie beings with Eugene Pratt (Zach Cregger) and Tucker Cleigh (Trevor Moore) as little kids. Tucker wants to go and see Eugene's brother's rare baseball collection so they go inside Eugene's brother’s closet and steal the box. Inside, they also find a playboy magazine. Eugene is disgusted by the site but Tucker is fascinated and curious, asking questions like "Where do they pee out of?" Tucker leaves the room with the magazine. Three weeks later, Tucker is checking out the ass of another girl and making sexual remarks like a teenage pervert while Eugene looks on in disgust.
Fast forward about eight years. Eugene and Tucker are 18 years old and about to graduate. Little has changed though as Tucker continually checks out girls and makes perverted remarks while Eugene is still disgusted and tells Tucker to cut it out as he now has a girlfriend and feels uncomfortable checking out other girls. Candace walks by and Tucker makes a sexual joke about her epilepsy, causing her to beat him up.
Eugene goes to speak at an assembly with his girlfriend Cindi Whitehall (Raquel Alessi) while Tucker watches in the crowd. They inform the middle school kids listening that they are abstinent and they are trying to encourage everyone to be abstinent to prevent the spread of STD's. Eugene tells them about his brother who had sex too early and got an STD as a result and then shows them a picture of it, horrifying the kids.
Later that night, Eugene climbs up a tree and sits outside Cindi's window and proclaims his love for her. He then suggests they go to a party after prom to have fun. Cindi casually asks if this means that they are finally going to have sex but Eugene firmly states no, saying that he does not want the same thing that happened to his brother to happen to him. Cindi looks disappointed but agrees. Eugene then realizes his mistake and calls her and promises her that they will have sex at the party.
As Eugene is getting ready for prom, a limo drives up, courtesy of Tucker. Inside the limo are Horsedick.mpeg (That's the character's name) and his two ladies. Eugene is upset at this, preferring a nice and quiet environment. When Eugene goes to pick up Cindi, her parents look suspiciously at the limo (especially when a naked girl pops out of the roof) but they let the two go.
After the prom, the group all heads over to the party. It is a typical after prom party as people are getting drunk, beating each other up, and making out all over the place. Cindi tells Eugene that she will go get the key to the master bedroom and to meet her upstairs in five minutes. As she leaves, Eugene begins to get really nervous. Tucker decides to solve that by getting him totally drunk. Eugene gets really drunk and then shouts that he is going to have sex, only he takes the wrong door and ends up falling down the stairs. A toolbox, followed by a bookshelf, fall on him and he blacks out.
Fast forward four years later. Eugene wakes up to Tucker hitting him with a baseball bat. Eugene is furious but Tucker is ecstatic, stating that the baseball bat trick work and he's awake. Eugene is confused so Tucker explains. When Eugene fell down the stairs, he blacked out and fell into a coma for four years. No one expected him to wake up. Eugene then asks why only Tucker has waited for him and demands to know where everyone else is. Tucker states that his family moved away because they thought he was dead while his girlfriend Cindi went off to college and that Tucker lost contact with her. An angry Eugene tries to get out of bed but he falls to the ground and shits himself. The doctor rushes in and explains Eugene has to be careful because although he is healthy, he needs to give his muscles time to get used to physical activity. Eugene thanks Tucker for standing by him, but asks him to leave, saying he needs some time to sort everything out.
Tucker is at his job now. He takes photographs of families. One family comes in, and Tucker has the mom pose with her breasts sticking out as though she was a model. His boss later yells at him for this but Tucker turns a deaf ear as his new playboy magazine has come in. Suddenly Tucker gasps and runs straight for the hospital. He shows Eugene the centerfold of his magazine. It’s his girlfriend Cindi who is now Miss March. Eugene is shocked that Cindi would do something like this but Tucker shouts that this is perfect. He tells Eugene that there is the annual playboy party coming up on Saturday. The two can go the party, Tucker can get laid, and Eugene can profess his undying love for Cindi. The party is on Saturday and today is Thursday, so Tucker tells Eugene he has three days to learn how to walk properly again and learn how to control his bowel movements (he still can’t stop himself from shitting). Unfortunately, their plan is cut short when Tucker bursts into the hospital and kidnaps Eugene. On their way out, they run into Tucker’s girlfriend Amber (the one he had made fun of earlier in the movie because of her epilepsy) who has blood all over her face and screams out that she wants to kill Tucker. Eugene demands to know what is going on but Tucker can’t explain as he forces Eugene into the car and drives off. Unfortunately, they are also being chased by angry firemen because Amber’s brother is a fireman. The firemen hose their car and throw axes at it but ultimately the two are able to escape. Tucker then tells his story.
Tucker and Amber were on their thirteen month anniversary date. Amber had given Tucker the same pipe Hugh Hefner smokes. In return, Tucker gave Amber a stripper pole. He urges her to try it and do a dance for him and eventually she gets into it. She does a lap dance for him and then bends down to give him head. Tucker enjoys it and then turns on a strobe light to make it kinkier. However, the strobe light triggers Amber’s epilepsy and she begins to have a seizure. Since she can’t control herself, she bites down on Tucker’s dick. Tucker screams loudly but cannot get her off. In desperation, he grabs a fork off the kitchen counter and stabs her with it repeatedly. Eugene is horrified at what Tucker did but Tucker shrugs it off when he hears Horsedick.mpeg on the radio. Apparently Horsedick has become extremely famous as well and still keeps in contact with Tucker. Eugene suggests that they go see Horsedick to help them get into the playboy mansion and Tucker agrees.
As they are driving, Eugene falls asleep and has a horrible nightmare of Cindi being a slut and sleeping with every single guy. Eugene suddenly wakes up, only to see Tucker snoozing. He quickly wakes up Tucker and orders Tucker to stop at a motel so they can get some rest. At the motel, Tucker lights his special pipe, only to accidently set the whole room on fire. The firemen arrive but one of them recognizes Tucker and chases after them. Eugene and Tucker get away and continue driving.
Eugene and Tucker go see Horsedick, who is glad to see them, although he constantly reminds Eugene to call him by his full name, Horsedick.mpeg. They ask for his help and he agrees and they board his bus to go to the playboy mansion. On the bus, Eugene reveals that he is a virgin, and Horsedick is disgusted. He orders Eugene to go have sex with one of his girlfriends but Eugene refuses. Tucker quickly takes the invitation and goes to the bedroom with the girl, but the bus hits a bump and she falls out the window, much to the horror of Tucker. Meanwhile, Eugene and Horsedick are getting high and Horsedick is lamenting over his failed relationship with one girl, which is why he does not do relationships any more. He mentions that he just bangs girls now, especially all the playboy ones. Eugene quickly asks if he’s done all the playboy girls and Horsedick smiles and says yes, including Miss March a.k.a. Cindi. Eugene is furious and slaps Horsedick, leading to them getting kicked off the bus. They are then picked up by two hot lesbians who offer them a ride but say they have to drive because they want to have sex in the backseat. Eugene and Tucker gladly agree but crash several times because they are distracted by all the lesbian sex in the backseat.
Eugene and Tucker finally arrive at the playboy mansion, but wonder how they are going to get in. They try and use the lesbians but the bouncers only let the lesbians in and throw the two out. Suddenly the firemen arrive, still looking for Tucker as Amber suggested that Tucker would come to the playboy mansion. They crash the party, looking for Tucker. The two quickly use this as an opportunity and don firemen outfits and blend in so they can get into the party. Inside the party, Tucker tries to hit on numerous women, with no success. Suddenly the firemen see him and chase after him. Tucker runs into the lesbians and asks for their help in opening the locked door, saying that there are beds and jacuzzis are on the other side. One of the lesbian girls uses her tongue to unlock the door (very resourceful) and the three go inside and lock the door. They are now in the east wing and Tucker runs into another door and finds Hugh Hefner. Tucker is awestruck and states the Hef is his idol and that he uses all of Hef’s advice to help him succeed in life. Hef then asks about that success and Tucker relents, stating that he keeps striking out with women but he doesn’t know why. Hef sits him down and shows him a picture of a very ugly woman. Hef states that she was his neighbor and that he fell in love with her but she died at 18. Hef says the he’d trade all the women he has been with for one more afternoon with that girl. Tucker is shocked and asks why and Hef explains that it’s not about the quantity of the relationship but the quality, that there is a bunny inside all girls and that the key is finding that bunny and then holding on to that girl forever. Tucker reflects and then states that he doesn’t have to stab Amber with the fork to appreciate her. Hef smiles saying that he is glad Tucker learned something but that he’s calling security.
Meanwhile Eugene is desperately trying to look for Cindi. He asks a bunch of people, but everyone refuses to tell him, thinking that he is a stalker. He finally sees her walking down the stairs and shouts out her name but suddenly he is grabbed from behind by a security guard. Luckily, Cindi recognizes him and rushes to the room where Eugene is being held and gives him a big hug. However Eugene is angry and humiliated and begins to rant. He asks why she left him, why she decided to pose nude for everyone, and why she decided to have sex with every guy she sees. She tries to explain but Eugene cuts her off, saying he does not want any of her excuses and asks her to think about how she feels if she was in his shoes and if she was abandoned by the one person she loves only to see her go off and pose naked for everyone. Cindi finally gets a word in, and she quietly states “Everything I’ve done, I’ve done for you.” Eugene is confused and Cindi asks him how he thinks his four years of hospital bills were paid. She then states how his family had given up on him and refused to pay his bills anymore. Cindi tried to pay his bills with part-time waitressing but she realized that it wouldn’t be enough. She then tried modeling and realized that it would pay enough for his bills. She also calls the hospital every Monday to check on Eugene and Eugene realized he woke up on Wednesday and left on Thursday. Eugene is suddenly dragged out by security before either one of them can say anything more.
Outside Eugene runs into Tucker, who is also being dragged out. Tucker is then snatched by the firemen and about to be executed. However Tucker screams out to Amber that she is the only one for him. He then tries to deliver a heart felt, sensitive statement professing his love for her but it comes out pretty badly as all he says is that he can put up with her seizures as long as she doesn’t chew his dick off. She accepts it however and runs over and kisses him. Meanwhile, Eugene is about to do the same thing to Cindi until Horsedick.mpeg comes over, wanting revenge for Eugene slapping him and shitting on his bus. However Cindi comes running out and then tells everyone that she didn’t sleep with Horsedick and that Horsedick tried to seduce her but that he doesn’t even have a dick. Horsedick tries to laugh this off until his friends realize they’ve never actually seen him have sex. They pull off his pants and they see that he has no dick. Horsedick is humiliated and runs off.
Eugene goes up to Cindi and apologizes for everything, saying that he still loves her. She says she loves him too and kisses him. They go back inside and she tells him to meet her upstairs in five minutes. Tucker points out that Eugene’s first time will be in the playboy mansion with Miss March. He congratulates him by giving him a drink. He then says that Eugene needs to be ready and should get really drunk. Eugene agrees and downs another shot (uh-oh déjà vu of what happened at the first party perhaps?) as the movie ends.
After the credits, the doctor is explaining to his fellow doctors that he has learned that the best way to get someone out of a coma is to hit them with a baseball bat. He hits the patient once, twice, three times, but the patient doesn’t respond. Finally after the fourth time it works and the patient gets up…it’s the girl from Horsedick’s bus, the one who fell out the window while she was seducing Tucker. She screams out “I hate you Tucker Cleigh” as the scene ends.
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