Plot

Four teenage boys enter a pact to lose their virginity by prom night.

Jim, Oz, Finch and Kevin are four friends who make a pact that before they graduate they will all lose their virginity. The hard job now is how to reach that goal by prom night. Whilst Oz begins singing to grab attention and Kevin tries to persuade his girlfriend, Finch tries any easy route of spreading rumors and Jim fails miserably. Whether it is being caught on top of a pie or on the Internet, Jim always ends up with his trusty sex advice from his father. Will they achieve their goal of getting laid by prom night? Or will they learn something much different?—Film_Fan

At a high-school party, four friends (Jim, Kevin, Finch, and Oz) find that losing their collective virginity isn't as easy as they had thought. But they still believe that they need to do so before college. To motivate themselves, they enter a pact to try to be the first to "score." And of course, the senior prom is their last best chance. As the fateful date draws near, the boys wonder who among them will get lucky. More importantly, do they really want to do it at all?—Andy Zimolzak <zimolzak@jcisd.k12.mi.us>

At East Great Falls High School in Michigan in 1999, 4 students are Jim (Jason Biggs) a lustful, naive, and bumbling student, Finch (Eddie Kaye Thomas) an educated and sophisticated student who plays golf and wears sports jackets, Kevin (Thomas Ian Nicholas) an earnest student, confident and charming, but struggling to finally have sex with his girlfriend Vicky and Chris "Oz" Ostreicher (Chris Klein) a handsome and oafish school jock. They are all virgins, in sharp contrast to popular lacrosse player and arrogant jock Steve Stifler (Seann William Scott), whose wild, extravagant house parties they are regularly invited to.

At one of Stifler's parties, the 4 guys try to get together with a girl. Oz is humiliated by an older girl, who laughs him off and says that he comes off too strong. He needs to tone it down and listen to a girl.

Finch is too late for the party and Jim attempts to talk to Czechoslovakian exchange student Nadia (Shannon Elizabeth), but fails completely. Kevin struggles to seduce Vicky, who fears he only wants her for sex and insists on waiting for the perfect moment to lose her virginity. During Stifler's party Kevin and Vicky (Victoria) (Tara Reid) go upstairs, and she performs oral sex on him. Vicky was really happy about being accepted into college and wanted to celebrate with Kevin. Vicky breaks up with Kevin when she finds Kevin boasting about the blow job.

A dorky classmate, Chuck Sherman (Chris Owen) claims to have done so at a party at fellow classmate Steve Stifler's house. Sherman pretends to be a sophisticated sex robot sent back through time to change the future for one lucky lady. The 4 guys make a pact to lose their virginity before their high school graduation. Later, while eating breakfast in a restaurant, they toast each other to 'the next step' and formulate individual plans to achieve sexual success.

The guys decide to change their strategy after Stifler's party. It has to be valid, consensual sex, meaning no prostitutes. Prom is their last chance and is exactly 3 weeks away.

Kevin immediately sets out to win Vicky back, but has to work very hard to even get a chance with her, and begins to seek advice from others. Vicky's best friend Jessica (Natasha Lyonne) reveals to Kevin that, despite his thinking otherwise, Vicky has never felt an orgasm from Kevin, and that he has to work on that above everything else.

Kevin learns how to give head to girls by a book owned by the long generation of students who studied at the school, and which was hidden in the library, shown to him by his brother Tom (Casey Affleck). Both Jessica and Tom divulge their advice only after Kevin stresses he wants to make Vicky happy, rather than simply taking advantage of her for his pact. Kevin finally seizes a chance to make things up with Vicky, and performs oral sex on her in her bedroom using his new techniques. Vicky experiences an intense orgasm and is driven wild by Kevin, winning him the promise of sex at the prom after-party in the process.

Oz, who is on the high school lacrosse team with Stifler, joins the jazz choir to pick up girls, as the girls in the band know little of his reputation as an insensitive jock. Oz meets Heather (Mena Suvari) a sweet-nature and virginal choir girl, who is in the same group as Oz. Heather is attracted by Oz's sensitive side and befriends him. She asks Oz to prom. But then she sees Stifler making fun of her as a sex toy to Oz and is put off. A desperate Oz volunteers to become lead vocalist alongside Heather to try and regain her trust. He succeeds when she catches him tirelessly rehearsing alone in the theatre, and pays him a visit after-hours at the sandwich bar he works at to reconcile. Their relationship is dealt another blow when Oz realizes his last ever lacrosse game for East Great Falls clashes with the choir competition.

Oz decides to abandon the lacrosse game halfway-through and rushes over to the music hall, where he makes it just in time. He performs the long-awaited duet with Heather to rapturous applause from the audience, including Kevin and Jim themselves.

Finch at first appears to have no plan, but Kevin's suspicions arise when corroborative rumors begin flying around the school that Finch has legendary sexual prowess, has had relations with older women, and that he even knocked out Stifler in a fight. Kevin investigates and discovers that Finch paid Vicky's friend Jessica (Natasha Lyonne) $200 to spread rumors around the school of his sexual prowess (that he has a huge penis), hoping that it will increase his chances of success.

The rumor grows to an extent that girls refuse a date with Stifler on an outside chance that Finch might ask them out to prom. So, Stifler mixes a powerful laxative in Finch's drink that forces a sanitary nut Finch to go to the girl's bathroom in the school (as Stifler had locked the boys bathroom), when he would never go to the bathroom outside his own house. Finch experiences an explosive diarrhea, and Stifler gathers a crowd to mock him, ruining his carefully crafted reputation and now Finch is looking for revenge from Stifler.

Jim is caught by his father masturbating, and then trying to have sex with apple pie as his friends told him that's what third base feels like. His father walks in on the act and is left stunned and disappointed by his son's actions.

Jim pursues Nadia (Shannon Elizabeth), an exchange student from (the former) Czechoslovakia. Nadia comes over to study with Jim at his home & has to change after her Ballet class. Jim leaves the room to give Nadia space but had set up a webcam on his desk (based on Stifler's advice), so they can watch her change clothes. Jim unwittingly shares the live-stream with the school's entire e-mail directory, letting everyone watch as Nadia undresses. Upon Nadia's arrival, Jim sets up the webcam and dashes across the street to join Kevin and Finch at Kevin's house.

Jim was watching the broadcast from Kevin's house, who tells him that this is his best chance with Nadia. Jim watches Nadia fondle herself after she finds Jim's collection of erotic magazines which were gifted to him by his father. Kevin and Finch force Jim to go back and seduce her while the moment lasts. Nadia is furious at finding Jim in the room but then relaxes & wants to have sex with Jim. This ends with Nadia forcing Jim to strip and dance for her while she reads his pornography. By now, various groups of East Great Falls seniors, including members of Blink 182, are watching the live action in excited anticipation. But Jim ejaculates prematurely twice & is humiliated across high school. Nadia has to leave town after her sponsors see her video on the internet and don't approve of it.

In his desperation, Jim asks band geek Michelle Flaherty (Alyson Hannigan) to the senior prom as she is apparently the only girl at his school who did not see what happened on the webcam broadcast.

The big prom night arrives. The guys are pretty sure that they are not going to get laid. Finch is the only one of the four who attends alone, but Jessica, also alone and feeling guilty for taking his money, offers to dance with him, even giving him a brand new hip flask as a gift for his troubles. The prom itself is cheap, tacky and uneventful and derided by most of the students.

Kevin insists Jim, Oz, and Finch fulfill their pact and lose their virginity, but they refuse, frustrated at the social pressures to have sex for the sake of it, and accuse Kevin of using the pact to hide his fear of losing his virginity.

At the prom Vicky finds out that Sherman never had sex with any girl at Stifler's party. The said girl feels offended and announces that she never had sex with Sherman at Stifler's party. Sherman is exposed, gets nervous and wets his pants. After learning that Sherman lied about having sex, the boys reconcile with Kevin, who admits he is afraid. The four boys excitedly catch the bus to Stifler's huge post-prom party at his mansion on Lake Michigan.

Kevin and Vicky go upstairs to have sex, but the whole act is very awkward for both. Afterwards, Vicky breaks up with Kevin as she is not looking for a long-distance relationship with Kevin.

When Heather starts avoiding Oz, he confesses the pact to Heather and renounces it, saying that just by them being together makes him a winner. They fall in love, begin a relationship and wind up making love on the porch at the prom.

Finch meets Stifler's mother (Jennifer Coolidge). After some sophisticated, upper-class conversation and flirting, she becomes aroused by Finch's precociousness, and they proceed to make love on the snooker table as the party goes on through the night.

Jim and Michelle have sex after he finds out that she is actually not as much of a band geek as she let on and she saw the "Nadia Incident" after all. She accepted his offer to be his date because of it, knowing he was a "sure thing," but she makes him wear two condoms to combat his earlier "problem" with Nadia. Jim is surprised to discover that Michelle behaves unexpectedly aggressively in bed. Jim finally gets to have disaster-free sex, but Michelle is dominant and violently aggressive, shouting abuse at Jim, roughing him up and smashing things up with her hands and feet out of sheer passion.

In the morning, he wakes up to find her gone and realizes that she had used him for a one-night stand, which Jim thinks is "cool."

Later on, Kevin, Oz, Jim and Finch all go to their favorite hang-out restaurant, the fittingly-named "Dog Years", for breakfast. Far from celebrating their pact with stories, they all remain very conservative and hushed about their experiences the night before, with Oz gleefully refusing to even confirm whether he had sex or not. Regardless, the four lads are now collectively happier than they ever were before, and once again toast each other to 'the next step' as they prepare to leave high school and move away to university.

Jim sets up his webcam in his room once again, and stripping and dancing to country music. Nadia is on the other end, back in her home country, smiling and laughing at Jim. His father walks in on the act, but sees the funny side. He walks out and starts dancing down the corridor, presumably to make love to his wife, as he seductively mutters "sweetheart!".