The film takes place at the fictional Camden College, a liberal arts school in northeastern New Hampshire and it set in the late 1980s. The opening sequence introduces the three main characters - Lauren Hynde (Shannyn Sossamon), Paul Denton (Ian Somerhalder), and Sean Bateman (James Van Der Beek), in turn. They are three college students at an "End of the World" party, and although they don't interact at the party, they share a certain apathetic perspective.
Lauren is at the crowded dorm party trying to lose her virginity. She wants to go to bed with Victor, her stylish dreamdate, but is settling for Raymond, the handsome film student who can't keep his eyes off other girls' breasts long enough to get her into bed. They finally go upstairs, passing Sean along the way. Sean watches with them leave with the dark look that only a spurned lover can generate, tearing up what appear to be love letters as they go.
Upstairs, Lauren takes Raymond into a friend's room rather than her own and feeds him a joint, then passes out on the bed before they can go further. She wakes up getting fucked from behind, but doesn't seem particularly upset about it. Then she realizes that Joel is filming the whole episode on his vid camera and her sex partner is a 'Townie' from the party. She's still not too upset, sort of resigned. Then the door to the room bursts open and two other guys stumble in looking for a place to stash their keg of beer, Joel complains about his 'light', the Townie starts to climax and then pukes at the same time all over Lauren's back. Suddenly the film goes into rewind.
(Note: If you're totally turned off at this point, stop reading. If you're only fairly disgusted, but intrigued, this opening scene sets the tone for the whole film.)
We "rewind" downstairs to the party where we meet Paul, a very pretty and confident young guy who's obviously at least bisexual from first glance. He's chatting up with some other guys and has a vibe going with one of them. He suggests the two of them retire upstairs for some dope, but when they get up to the other guy's room and Paul puts the moves on, the other guy chickens out, punches Paul a few times and throws him out of his room while loudly defending his heterosexuality. Paul lies humiliated on the hall floor and has a cigarette, mentioning in voice over that his date of moments before came out of the closet a year later and became a huge queen while slagging Paul's virility.
Rewind downstairs again to meet Lara (Jessica Biel), Lauren's roommate and the resident "dumb-blonde" sex queen party-girl who seems to live for getting messed up and then laid.
We learn in voice-over that she does the entire football team the next year, but years later is a Senator's wife with four kids.
Finally we meet Sean, who's sporting evidence of a recent beating, though it's impossible to tell if he was the winner. He looks like he didn't come off too bad at least. He does his own voice-over, a recurring trend. He complains that he rarely feels any true emotions himself (classic sociopath symptom), but enjoys vibing off other peoples' as an 'emotional vampire'. He can project a dark intensity and focus that women find very intriguing.
Sean finishes ripping up the letters and notices a pretty young blonde girl (Kate Bosworth) across the room.
He catches her eye and holds her attention as he walks across the room to her, noting the sexual promise of her lips. The blonde thinks she recognizes him and in fact Sean thinks he fucked her the first week of school, several months ago, but he introduces himself as 'Peter the first-year'. He says it with the tone of one both utterly confident in his lie, and utterly amused at his own blatant audacity. The blonde is hooked and she introduces herself as Kelly. Sean and Kelly go upstairs and hit the sack. Kelly's turned on and completely drunk but Sean's having trouble maintaining interest - something's missing. He finally realizes this is the first time in ages he's had sex while not drunk.
End Credits. Rewind WAY back to near the beginning of first term at the college months earlier.
Lauren walks through campus, Sean wakes up under a tree surrounded by beer cans.
Sean goes up to his campus mailbox and picks up a love letter. It obviously is one of a series of anonymous love-notes, and Sean's really getting off on them. Not the idea of love, or loving someone, but that someone loves HIM.
Then he goes to see his drug connection, a distributor in the local town. This guy Rupert may be small college town, but he's a serious drug dealer who sniffs too much of his own product and hates a debtor, while Sean still owes from last year. However, Sean manages to bs his way out of a beating and into an advance on some coke to deal on campus.
Sean goes to the campus canteen for some food but it doesn't meet his approval, so he scowls at the girl serving him and dumps the whole tray in the garbage.
We catch up on Lara and Lauren, new roommates, and learn that Lauren is definitely a virgin and saving herself for Victor Johnson, her former boyfriend, currently attending college in Europe. Lauren has a book full of venereal disease photos to help distract herself from her raging hormones and deny temptation.
The Start of the World night party, a wickerman rip-off in some field near the college. Paul goes vamping up to Mitchell (Thomas Ian Nicholas) (the same guy who will beat up Paul later), a fairly straight guy who obviously had at least a one night stand with Paul and now wants to sweep it under the rug. He practically runs away from Paul and into the arms of Candice (Clare Kramer), a fellow student who's looking for some action and isn't shy about it. She invites Paul along for a threesome and Mitchell almost has a heart attack, but Paul bows out, much to Mitchell's relief. Paul wants Mitch to himself or not at all.
Sean sits in Marc's (Fred Savage in a hilarious and unrecognizable cameo) room, trying to collect some drug money he's owed. Unfortunately for Sean, Marc's too distracted with lying on his bed naked, shooting smack between his toes and smoking up while playing the clarinet. Badly.
Sean shows up at the party looking for some beer and distracton from his troubles and catches Paul's eye. Paul invites him out for Mexican the next night, only getting Sean's attention by offering to pay. Sean agrees but is too uninterested in the whole conversation to catch that Paul's hoping for a hookup.
The next morning, Saturday, Lauren wakes up studiously early and gets properly ready for her morning philosophy class, arriving at the class room early. Sean wakes late, smokes a joint, hits the crapper, puts on dark sunglasses and stumbles over towards class.
Lauren finds the young Professor Lawson (Eric Stoltz) sleeping off a drunk in his office behind the class and delightedly sneaks a couple pulls on the joint still smoldering on his desk before leaving. She runs into Sean in the hallway outside class and tells him it's cancelled, where his rough uncaring confidence catches her fancy, and her obvious attraction catches his attention. Lauren wanders away leaving Sean wondering if she's his mystery pen-pal.
That night... ANOTHER PARTY. Actually, the Saturday night pre-party party. Lauren decides enough is enough, she's going to get rid of her pesky virginity and Sean's the man. Unfortunately, Sean doesn't show right away.
Meanwhile, Paul is increasingly infatuated with the idea of getting together with Sean, convincing himself that the feeling must be somewhat mutual. He's getting ready for their 'date' when some of Paul's more flagrantly gay friends burst in and shanghai Paul into helping take another od'ing friend of theirs to the hospital. Everyone's freaking out on the ride to the hospital except for Paul, who's much more worldly than the others and convinced their friend is just passed out.
He's right. When they get to the hospital a jaded doctor who's sick of having drunken students stumble into his Emerg takes one look and starts calmly pretending that the guy's dead, just to freak the others out. However, the guy wakes up and his gay friends drag him back out to the car, much to Paul's annoyance and disgust at their naivete.
At the party, Sean finally arrives just in time to run into Paul, who apologizes for missing their dinner date. Sean has no clue what he's talking about, but agrees to go up to Paul's room on an offer of some dope to smoke. Lara and Lauren see them go, but don't believe Sean could possibly be leaving to sleep with Paul.
Lauren leaves the party with Prof. Lawson for lack of her first choice and goes back to his office, where she's nervous and uncomfortable. Lawson sleazily insinuates that he can't sleep with her for fear of his tenure but he hears much of her oral skills. Lauren obliges without protest, although it's obviously her first time.
In Paul's room, Sean smokes up and watches porn while ignoring his host, while Paul fantasizes about making out with Sean. The next morning they're still there, interrupted by a phone call from Paul's mother. Sean leaves, 'borrowing' a number of Paul's cds at the same time, while Paul agrees to meet his mom and some family friends for dinner.
Sean picks up another love note at his mail box - this one just says 'Tonight's the night'. He's more convinced then ever that Lauren his secret admirer.
Paul meets his mother (Faye Dunaway) at an upscale hotel in town for dinner, where his childhood friend Richard "Dick" Jared (Russell Sams) bursts into the hotel room where Paul's staying. Dick is strikingly handsome, wildly gay, just plain wild, and obviously had a thing with Paul when they were younger. One thing Paul looks upon fondly with nostalgia but would like to leave behind. Dick swigs straight from a bottle of bourbon and tries to seduce Paul until their respective mothers burst in.
Paul's mother and Dick's mother (Swoosie Kurtz) are surprised, slightly tipsy themselves, but also clueless. These women are rich, oblivious, shallow, and utterly unable to deal with their children. Luckily for Paul's mother he's reasonably responsible, at least with his own life. Dick's mother is getting dragged along behind a wild stallion. The older women leave the boys to get ready for dinner, the boys go wild for 15 minutes.
Paul phones the dorm to speak to Sean, who's completely indifferent and eventually hangs up on him. Paul finally allows himself to believe that any mutual attraction was only in his mind.
Back at the hotel restaurant, Dick lounges gorgeously and sucks back drinks while disrupting any attempt at conversation, until finally he storms off in a pretend huff when he gets bored. The mothers deal with this by discussing their respective car colors. Paul orders his mother another drink when she can't make up her mind without someone else's help.
The next party - Dress to Get Fucked. People run around in various simple erotic costumes and states of undress. Lauren has definitely decided to give herself to Sean, much to her friend Lara's secret jealous rivalry. Sean is at the party, wearing his usual sweater and chinos, eating 'shrooms, looking for Lauren and looking for sex, but she's not there. However, Lara is in a baby-doll, looking to bag Sean before Lauren can.
Next thing Sean knows, he and Lara are on her bed going at it. Lara's enjoying things and oblivious, while Sean completely wasted on 'shrooms. He can only enjoy himself by covering Lara's face with his hand so he can't see her, and imagining Lauren in her place. After he cums Sean falls off the bed, then vows not to do 'shrooms again. At least not while looking to get laid.
In a dorm bathroom, an unknown girl prepares to commit suicide. She climbs in a tub of warm water and slits her wrists, doing it right. There's pain, then eventually she drifts off, sifting through her memories as she does so. It becomes clear that THIS is Sean's secret admirer. She's the girl from the canteen who saw him every day at meal time, watched from afar at every party, never approached him, and was never noticed at all. Then she saw him leave the party with Lara.
Lauren returns to her room, while Sean's pulling up his pants. Sean tries to recover by claiming 'I only slept with her (Lara) because I love you'. Lauren staggers out and into the bathroom, where she discovers the suicide.
The next morning an ambulance takes away the body and Sean tries to make up with Lauren, even though they never really had a relationship at all as far as she's concerned. No one knows about the love notes and their true author of course. Lauren blows him off.
After failing to make a dent in Lauren's refusal, in frustration Sean tries to hang himself in his room, though he's obviously not really trying and just pulls the hook out of the ceiling. Then he downs all the aspirin and Nyquil he has in his bedside table, but just wakes up the next morning having puked all over himself and wet the bed. This snaps him out of the funk and he then manages to lure Lauren to his room in a moment of her weakness and potential forgiveness, just so he can fake a suicidal slit-throat in front of her, then yell Surprise!. She's non-plussed and decides Sean's a bit psycho and she definitely wants nothing to do with him.
Sean gets no more love notes.
Lauren's ex-boyfriend Victor (remember him?) (Kip Pardue)... returns from Europe and regales Sean and Mitchell at a diner with a two-minute montage of his travels, mostly involving taking assorted drugs in different cities, seducing attractive women, and masturbating in their presence in lieu of sex. Oh, and he almost had a threesome with a couple of terrorist swingers who subsequently bomb a tourist attraction.
Victor and Mitch want some cocaine from Sean, but he says he needs to go meet his connection to get it. Victor doesn't trust Sean (he's no idiot) and after paying the $300 tag insists that Mitchell go along to ensure that Sean doesn't just pocket the cash. Sean insists on taking Mitchell's new Mercedes and driving, and Mitchell agees (he's an idiot).
They get to Rupert's house (remember him?) (Clifton Collins, Jr.) and head inside, much to Mitchell's consternation (he's a lite-weight), where the drug dealer's having a little get-together with some very large bouncer-type friends. Rupert's in the kitchen sawing up bricks of marijuana with an electric knife. He isn't too impressed with the $300 since Sean owes him $3k, and Rupert's enforcer picks up a baseball bat to do some damage until Sean points at Mitch and says those immortal words: "He's got it."
Rupert's so coked up he actually believes this, and all his heavy friends are converging on the kitchen for a bruising, while Mitchell freaks and denies everything. Much to everyone's surprise, Sean then relents and admits that Mitch doesn't have any money, then quickly jumps Rupert and manages to grab the knife in the scuffle. Mitchell and Sean escape out the back door before Rupert can shoot them, Mitchell squealing like a little girl. Sean also drives back to the university because he kept the car keys.
The entire thrill ride has been a high for Sean and he's stoked and laughing his head off, while Mitchel is traumatized and practically wetting himself. Sean leaves Mitch cowering in his car with the coke Sean promised, which was in his jacket all along.
Lauren hears that Victor is back and perks up, prettying herself for a trip his room with Lara's help while staring at Victor's picture. She leaves to finally take care of business.
Sean catches up with her along the way and confronts Lauren again, trying to pry some caring from her by revealing that he attempted suicide for real before he faked it. Sean also confronts her with the love notes and how he's knows how she feels about him, but Lauren's just confused and of course denies having any idea what he's talking about. She also makes it clear that she's now convinced that no one can ever know anyone.
Lauren stalks off through the snow to meet Victor, while Sean is left standing frustrated and bereft, unsure whether she's telling the truth or not.
At Victor's dorm, Lauren walks in fluffing her hair and laughing to herself at Sean's bizarre behavior, knocks on Victor's door, and gives him a big kiss immediately upon opening. Victor is startled and doesn't recognize her, while Lauren doesn't really listen to what he's saying and breezily forgives him for not calling her to say he was back from Europe. Victor starts to pretend that he completely remembers Lauren, then realizes that no, he actually has no idea who this girl is. Victor's door glides open further to reveal a blonde in lingerie bouncing on his bed, who gestures at Lauren to come in. Victor asserts his complete ignorance as to who Lauren is and she stumblingly apologizes for the mistake and staggers away in apparent confusion.
(We are left in confusion - Victor comes off as innocent and Lauren guilty in their encounter, so was he really an old boyfriend and he's completely forgotten her (believable for Victor)? Or did Lauren just fantasize their whole relationship in her months of fetishizing the idea of giving herself to him? Who knows?)
Sean goes to his mail box, seemingly hoping for another letter but not really expecting one and meets up with Rupert and his enforcer waiting to administer a beating. Sean almost gets away but fails, receiving his lumps.
Christmas time, the End of the World party, the ending where we came in at the beginning. Sean stands in the hall holding his letters and his aches, while all our other players occupy their starting places. He tears up the letters, but instead of eyeing the blonde, turns around and walks out of the party. We flash to outside the dorm house and out walks Lauren, to discover Paul sitting on the porch. One provides smokes, the other a light, and they start walking across the dark campus.
(At this point you have no idea whether after Sean walked out the events from the opening sequence actually happened or not.)
Paul asks Lauren about the letters and she once again denies knowledge. Paul just shrugs. They come across the parking lot, where Sean has been sitting in the darkness on his old motorcycle, watching them walk across the campus. He roars off through the slush and snow as they watch.
Sean roars down the highway, musing only about what waits moments down the road. Depending on how much you sympathize with him, he is either in denial of his pain, or this is further evidence of his sociopathy and how little any of the previous events actually affected him.