The film opens in 1984. Matt Franklin (Topher Grace), his sister Wendy (Anna Faris) and his best friend Barry Nathan (Dan Folger) are hanging at a record store. Matt is going on about Tori Frederking (Teresa Palmer), his high school crush that he has had a thing for since sophomore year. His favorite story was when Tori and him were roped into playing seven minutes in heaven. He was too chicken to kiss her, but when people began making fun of him, Tori saved face for him telling everyone he was an amazing kisser. He has talked about her to the point Wendy and Barry know what exactly what he is going to say before he does. Barry tries to flirt with the cashier of the store, but fails miserably and causes a huge mess, toppling display cases.
Cue Title Sequence
It's now 1988. Matt has graduated from MIT...and works at Suncoast Video, moving around VHS tapes all day. He doesn't seem to like it, but it's a job right now. We see a blond woman move through the mall that all the guys stop and stare at. As she goes near Suncoast video, we see it is Tori and so does Matt. In a moment of panic, he runs to the back exit, tears his vest off, and pretends to go into the store as a customer. He lets himself bump into Tori and pretends not to know her, but she recognizes him as Matt Franklin, the really smart guy from their class. She asks him where he works, and he lies saying he works at Goldman Sachs. Tori is confused by that as there is no Los Angles GS branch but Matt shrugs it off. She is working in the financial area as well and is wondering if he is going to Kyle Matterson's (Chris Pratt) that night. Matt says sure. Tori doesn't see a clerk, and is wondering where he is. Matt offers for her to leave with the tape and he'll pay for it "when the clerk comes back." Tori thanks him and says she'll see him tonight. Matt calls Barry at work and is excited that Tori was flirting with him.
Barry works at a car dealership trying to get a customer interested in buying a car. When Matt calls, Barry pretends it is his boss, and he is trying to bring the price down. The customer doesn't buy it as Barry's boss is right behind him. Barry is fired for this stunt, and he is enraged because he deferred from going to college to work there. He gets picked up by Matt and Wendy, and they go back to their house for dinner.
At the dinner table, Matt's father Bill (Michael Biehn) comforts Barry, saying at least he took a shot at doing something. His words are directed towards Matt, as he feels like he isn't living up to his potential. Bill tells Matt he gave him the summer to figure stuff out and now that it is over, he needs a plan. Matt says he plans to work at Suncoast till he can figure out a plan. Bill is still not happy saying, he didn't give up a good chunk of his life savings so his son could sell videotapes.
Matt goes into his sister's room and finds out that she applied to Cambridge but is too scared to open the envelope. Matt tells her that the stories she has written are excellent, and Cambridge would be stupid to not accept her. Matt offers to open the envelope, but Wendy tells him no. She is afraid what Kyle would say (they are dating and about to move into a condo). The three of them get ready for the party and head out.
On the way there, Barry is getting progressively drunk over being fired and losing his shot at going to school. When Matt objects to the car they are driving (as it wouldn't fit with his story about working at GS), Barry tells them to drive to the dealership. He explains he has the keys to the building and the codes to the dealership, and his boss has the keys to a Mercedes 560L in his desk drawer. Matt and Barry attempt to disarm the alarm but the boss changed the codes thinking Barry would do something in retaliation over being fired. The alarm goes off, and Matt runs out in a panic. Wendy locks the door to the other car and tells him to man up. Barry grabs the keys and spins the car out to the road and Matt quickly jumps in.
On the road, both are amazed they just stole a car. Barry is especially happy because he has never driven this particular one before (his boss wouldn't let him). Matt offers to take it back, but Barry says he wants to help his friend get Tori and the car is key. "Tonight we are not thinking Matt, we're doing." Barry says. With that settled, they drive on, happily lip syncing N.W.A's "Straight out of Compton."
They get to the party where they realize there is a packet of cocaine in the glove box which Matt puts in his pocket. Kyle is hyping up that someone will ride "The Ball"; a large steel sphere made of various metals. Matt tells Kyle it looks suicidal, and Kyle replies that Matt has no balls to do it anyway. Matt quickly insults Kyle and leaves to go into the party with Barry.
In the party, Matt searches for Tori while Barry freaks out at trying to interact with these people. Matt bumps into an old classmate Carlos (Demetri Martin) who is now in a wheelchair but it is okay with it because he gets better parking and lots of girls. Carlos asks Matt where he works and Matt says GS. Carlos calls bullshit as he works there and there is no Los Angles office. Matt explains he is trying to get with Tori and asks that his cover not be blown. Carlos says he will think about; it will depend if he is getting sex with a girl whether or not. Barry asks for the coke from Matt and trades the keys for it.
Matt sees Tori and is about to go up and talk to her but she is first approached by Rick Herrington (Ryan Bittle) a guy she once dated. Wendy and Kyle join them. Kyle begins telling an embarrassing story about how he and Wendy were caught having sex in a pool by his grandmother with Wendy reluctantly going along with it. Matt joins them and attempts to make small talk with Tori using stuff he thought she was into. It fails horribly and he feels embarrassed.
Barry meanwhile, not being able to deal with interacting with people, does some of the cocaine. He thinks it had no effect, when it suddenly hits him. He goes out and starts hitting on every girl on the dance floor including the gothish Ashley (Michelle Trachtenberg). One of the guys, Tyler, has a girlfriend and challenges him to a dance off.
Meanwhile, Matt talks to a guy about how though people get older, nobody really changes. However, Tori despite what Matt thought is bored silly talking to Rick so when she sees him, she uses him as an excuse to leave. They talk for a bit but go inside when they hear about Barry's dance off.
The kid, Tyler begins the dance off with some impressive moves. It is clear that Barry cannot compete. Barry tries but winds up falling down to the laughs of the crowd. Still, Barry presses for another round. Tyler does his, and Barry mocks the whole thing, culminating with kicking Tyler in the nuts with a crane kick (a la Karate Kid). This starts a fight with the two but Matt intervenes. Barry responds by kicking Tyler in the nuts again and running off. At the same time, one of Tori's friends is choking, and Matt thinking Tori is the one choking puts her in the Heimlich maneuver. Tori is mad and explains it was her friend, who she proceeds to save.
Matt is incredulous about how badly he is doing. He tells Tori she was his high school crush and he just physically assaulted her in front of a bunch of people and he is extremely embarrassed. Lucky for him, this finally breaks the ice with Tori and she dances with him to "Everybody have fun tonight" by Wang Chung.
Kyle cuts the music and brings up Wendy to the stage and proposes marriage. Matt says "no" but Wendy says yes to the happiness of the crowd.
Barry is outside drinking a wine cooler when Ashley comes up to him. She thought his dance was cool a sort of "anti-dancing" making fun of the bullshit people do. Barry quickly comes on to her, asking if she wants to get naked. Ashley laughs, saying that was quick even for her and she gets naked a lot. She licks his face and tells her to find her later. Barry smiles.
Matt talks to Wendy and tells her he objects to the proposal saying it is a big decision. Wendy tells him at least she is making them, he's too scared to make any decisions. Matt tells her Kyle would not want to move with her if she got into Cambridge and if she got married everything would be tied up in a bow, where she wouldn't have to think and just be a housewife. "I was wrong," Matt tells her leaving, "You would look good in an apron."
Tori's friends want to leave the party because they think the people there are losers and they rather network with rich bankers. Matt seeing this, races out and tries to stop her. He signals the alarm on the Mercedes which makes Tori turn around and is impressed that it is his car. He asks about the party and Tori offers to drive with him since she knows the way. Barry shows up and in order to get a ride with Tori's friends, bribes them with the coke.
Matt is driving and Tori explains the party is being held by her boss Pete Bering (Michael Ian Black). She explains that the main reason she probably had an offer to work there is because Bering wants to see her naked. She has held out (unlike her friends) and thus retains power over him and thus a shot at the company. Tori also notes that women always know when men are staring at their breasts and coyly shows him, looking away and daring him to look saying "now" the exact moment he is looking.
They arrive at the party where Tori's boss makes a pass at her which Matt sees. Matt attempts to diffuse the situation and when pressed with what he does, Matt says he transfers money from one market to the other until it returns to the starting point with a profit. This impresses Tori with his knowledge. Carlos comes up to the group and when given a chance to bust Matt chooses not too, saying Matt is one of the best at GS and actually just got promoted. Matt goes with it, and tells Bering a fake story about how a CEO got taken for 8 million due to sexual harassment. Bering, getting the message, quickly leaves. Tori is smitten.
Barry meanwhile, is drinking more and searching the party for girls. He sees an older woman Trish (Angie Everhart) but is afraid to approach her. She sees him too and with her partner Frances approaches him. She asks Barry if he is carrying coke which he replies that he is. Trish asks if he wants to have fun (i.e. drugs and sex) and Barry happily agrees.
Matt talks to Tori more about her job and she relates that it's good money and great benefits but stops mid sentence. Matt presses her on it, and she reveals she hates her job and he is blessed that he likes what he does. This makes Matt feel worse as he now knows he didn't have to lie as she is just as lost as him. Matt proposes they play "The Penis Game" in which they say the word over and over slightly louder until the other refuses to. Tori is resistant, but Matt counters since she hates her job it won't matter. She winds up screaming "PENIS!" to a bewildered party and they run off.
Barry is doing coke in the restroom with Trish and it seems she is into him. They begin to make out and then her partner Frances come in. Barry asks what he is doing and Trish says he likes to watch. She opens her blouse, exposing her breasts, telling Barry "It is not negotiable." Barry, not wanting to lose a shot with a hot woman, sighs heavily and replies, "I am going to try this."
Matt and Tori go outside and Matt suggests they do some yard hopping. They go next door where there is a trampoline. Matt gets on but Tori thinks it is a bad idea. Matt tells they are not thinking, but doing tonight. Tori gets on and jumps on. Matt mentioned their game of truth and dare but Tori claims to not remember. Tori says they should play to remember. Tori asks why Matt never asked her out. He says he never had an "in"; a moment that was good enough. He then says that is crap, he was just too scared. He asks if he had asked her then would she have said yes? Tori says that question isn't fair but replies that she would of said no. Matt is relieved, and explains that had he asked her, he would have hated her for being so cruel, so in the end her response is OK. Tori then dares Matt to get his lips close to hers without touching. Tori can hear his heart beat fast as they make out and when Tori asks if she should make it go double fast. Matt agrees and she begins to disrobe. Showing her breasts they both say "now" as he looks and proceed to have sex.
Barry is having sex with Trish but Frances is getting too close to his comfort and it freaks him out. He tries to leave, but Trish begins to punch him, thinking it is part of the game. Barry finally gets off, telling they are sick and reenters the party.
Tori and Matt are still on the trampoline after sex. She asks him how many times had he sex and he says "3 and a half." She laughs and tells him that's why she likes him, he is so honest. Matt cannot lie anymore and tells her the truth; he works at Suncoast video and not GS. Tori is shocked, thinking he just used her for sex, but Matt says that was not the reason at all, he was just afraid she wouldn't give him the time of day. Tori is not in the mood to talk and leaves in a huff. Matt kicks himself over his stupid decision.
Matt collects Barry and they leave the party. Barry is happy for Matt at first when he finds out he had sex with Tori. He is then mad at Matt when he reveals he told her the truth. "Why can't you give yourself one night?" Barry asks. Matt kicks himself some more, and Barry tells him he fucked up. Barry offers him some coke and Matt agrees as long as Barry takes the wheel. Barry is coked out of his mind though and no one is watching the road. They lose control and go down into a ravine.
Tori sees that Matt left without her and takes off her shoes, walking back to Kyle's party.
Barry says it could be worse, but Matt says it couldn't be any worse. Barry's airbag deploys and coats his face in cocaine. Then the police show up and the lead officer happens to Bill, Matt's dad. His father is understandably angry his son stole a car, and Barry tries to divert all the blame to himself. Bill tells them that they will probably get probation then spend the next couple years paying off the car but since Matt can get a good engineering job it shouldn't be too hard. Bill then beats on the car and causes more damage. Matt tells his father he will get an engineering job and he'll do whatever he wants. Bill asks his son "What do you want though?" Matt doesn't have an answer and apologizes for being such a "fucking failure". Bill says he isn't a failure because he hasn't truly tried anything. Bill leads the cuffed Barry and Matt to the squad car.
Back at Kyle's party, Kyle and Wendy talk about their future. Wendy tells him she applied to Cambridge in England and was afraid to tell him. He is not clearly not interested in her moving and opens the letter. Wendy didn't get in. She is heartbroken and Kyle seeing he was a bit of a jerk, tries to comfort her, telling her she can do her writing anywhere.
Bill brings Matt and Barry back to their house, telling them this is there one and only mulligan; they are going to pretend none of it happened. Bill talks to his son, telling him he just want his son to "take a shot." Matt says he doesn't know where to aim. Bill tells him anywhere, as long as he is doing it. They leave the two there but Matt begins to walk back to Kyle's to win Tori back.
When they get there, Kyle is trying to get someone to ride The Ball but is having few takers. Matt looks for Tori and finds her. He says he is sorry he lied about his job but that was the only thing he lied about; everything else, everything they experienced this night was real. Matt asks her if she known the truth from the beginning would of she given him the time of day. Tori says she didn't sleep with him because he was a banker, she slept with him because he was smart, funny, and most importantly honest.
With nothing left to lose, Matt volunteers to ride the ball. Wendy and Barry are against it but Matt persists. He tells everyone he works at Suncoast and lives at home. He has been so scared of living that he has missed his life. The thing is though, they are all lying to themselves about being happy and everyone is scared right now. So him doing this is saying "fuck it" to being scared. He gets in and is launched by Kyle. The Ball hits many cars then goes down a steep ravine to the horror of Barry and Wendy. Matt finally crashes through a fence into a backyard with a pool. The Ball begins to fill with water and Matt almost drowns, though he gets out in time.
Wendy is livid with her boyfriend and wants to find her brother and make sure he is OK. Tori offers to drive her.
Matt gets out of the pool only for Barry to throw him back into it in celebration. They leave and begin to walk back down the road. Wendy is glad her brother is OK. Matt finally goes up to Tori and asks for her number because he wants to take her out on a date. Tori replies that he was loser back then and now he is only a loser "who fucked me and rode The Ball." Wendy is happily shocked that her brother got somewhere. Matt apologizes profusely for his behavior, saying he will leave her alone now. Tori is touched by his remorse and gives him her number, admitting that riding The Ball was pretty awesome. They go back to the party and everyone cheers Matt.
Wendy has a big argument with her boyfriend. She tells him how quick he was to endanger her brother and how he was happy she was rejected from Cambridge. Kyle tries to play it off but finally admits that he was glad that she wasn't going to leave. Wendy says she is cancelling the movers and breaking up with him. Kyle pleads with her not to, but she is firm. Kyle breaks down in tears.
Barry finds Ashley while she smokes pot out of an apple. He tells her he doesn't know what he is going to do. Ashley says he could always go to college as there is a bunch of drugs and sex. She kisses him and he says "You make a lot of sense", as they have sex.
Tori gives Matt her number and Matt suggests they part ways for now before he messes it up again. She agrees and he kisses her before she goes. Tori tells him that was bold. Matt says it was the scariest thing he did all night.
Bill goes to the site of the The Ball and sees his son's Suncoast tag. He smiles that his kid finally took a shot at doing something and pockets the card so he won't have to report it.
Matt, Wendy, and Barry finally meet up and Matt suggests breakfast as they drive off. Matt may have not found what he wanted exactly to do with his life that night, but he now has the courage to finally make a decision.