The movie begins with geeky Ian chatting online with a girl. He has posted a fake picture of himself online as a hot football player. He and the girl flirt while he tells her about his fake football practice. She is turned on and sends him a picture of herself in a bikini. Not wanting to blow it, Ian signs off and goes to bed where he has a wet dream.
The next morning Ian finds his underwear messed and throws them in his hamper (missing it and hitting the floor). Just then Ian's dad and step-mom-to-be come into the room and excitedly announce their engagement. Everyone wants Ian to get up and hug his new step mom, but he is naked so he awkwardly waves at her. Her feelings hurt, she turns to leave the room and slips/falls on his dirty underwear.
Ian's older brother Rex drives Ian to work at a donut shop, Senior Donut (or something), in the mall. Rex is Ian's opposite. He rides motocross and has a really hot car that helps him to get girls. He encourages Ian to get laid before he turns gay. At Ian's work we see that he is attracted to his female co-worker. Their boss decides someone needs to wear the donut suit and pass out coupons. The girl hugs Ian and plays on his attraction to get him to do it once again. Ian puts on the suit and hands out coupons, but some jocks play a prank on him and stick a giant dildo on to the suit where Ian can't see it.
Ian eventually gets punched out by a dad protecting his daughter from the obscene donut. Ian's two friends just happen to be in the mall and come to his rescue. Felicia is a tom boy / Emo girl who is unhappily trying on dresses for her cousin's wedding. Lance is a confident ladies man. They make plans to go to a party later. Ian asks his female co-worker to go with him, but she says no. Ian's clothes get stolen from his locker, so he has to wear the Senior Donut suit home. Rex won't let Ian wear it in his car, so the suit is stashed in the truck and Ian leaves in his underwear.
Ian gets home and finds out that his female co-worker is really dating his younger brother. Bummed, Ian goes to the party alone. Lance works his magic on a girl and gets her to agree to take Ian's virginity. As they are just starting to make out, Felicia knocks on the door. It becomes apparent that Ian really likes Felicia, and he pretends like he wasn't with the other girl so that they can talk. Felicia tells him that she has fallen for someone, and Ian thinks she finally likes him back. He goes to kiss her, and she suddenly realizes what is happening and freaks out. Ian pretends he wasn't going to kiss her, but they are uncomfortable.
Ian goes back to chatting online with the girl from the beginning of the movie. It turns out she lives in Tennessee and he lives in Chicago. She promises Ian that if he drives to meet her she will go all the way with him. Ian tells Lance that he finally has a chance to lose his virginity, and Lance encourages him to steal Rex's car while the rest of the family is away for the weekend. Just as they are pulling out of the driveway, Felicia shows up because she was suppose to spend time at Ian's that weekend. Ian lies to her and says that he is driving to visit his grandma so she won't know the truth and think he is gross. She ends up deciding to come along and the guys can't figure out how to talk her out of it so they all leave together.
After driving for a while they stop for gas. Inside the station the woman attendant is crying. Felicia ignores her, but Lance comforts her. They end up driving to her parent's house so that the woman and Lance can have sex. Ian and Felicia are stuck talking to the parents, drinking purple soda, and listening to the two have sex. At this point it becomes clear that the person Felicia likes is Lance. The gas station's woman's boyfriend drives up with flowers, but he hears Lance and her in the other room. Lance is handcuffed to the bed and the woman tries some sex act that involves crapping on him. Freaked out, Lance tears the metal headboard off and runs out the door just as the boyfriend attempts to burst in on them. The boyfriend chases Lance into a corn field. Ian and Felicia take the car and chase after Lance, hitting the boyfriend with the car by accident and saving Lance. Lance gets into the car naked.
The three drive for a little while longer, but their car overheats. Felicia suggests that they all pee into the radiator. This works for about a second and then the car breaks down again. Ian and Felicia take off looking for help. Lance stays with the car. As the two walk down the road, they find a tree with hundreds of pairs of shoes hanging from the branches. Felicia throws her shoes into the tree even though they have a really long walk in front of them. Ian tries to stop her and tells her to be logical, but she hates that he is like that and never lives in the moment. Meanwhile Ezekiel, and Amish guy, drives past and offers to fix the car. At first Lance blows him off, but Ezekiel sarcastically calls Lance out on his stereotype. They hitch the car to the buggy and pick up Ian and Felicia down the road.
The Amish community offers to fix the car for free, and Lance, Felicia, and Ian go to an Amish barn party. It turns out there is some sort of Amish spring break like rite of passage occurring. Fall Out Boy holds a live concert, everyone is drinking and dancing, etc. Lance falls for Mary, a cute Amish girl, and Ian is upset when Felicia and Lance slow dance. Lance kinds squishes Felicia's heart and calls her his wing man. Felicia and Lance help a drunk girl leave the party and talk about their uncomfortable almost kiss.
The next morning the car is fixed. The work was done for free, but Ezekiel wants them to help out with some chores. Ian explains that he has to leave to meet the girl from the Web, but that they will stop by on their way back. Ezekiel gives them hell and doesn't buy it.
The three continue on to a carnival for some reason. Ian and Felicia are kinda uncomfortable with each other. Lance reveals to Ian that he knows Felicia likes him, but that she is off limits because Ian likes her. He also tells Ian to let her go because she doesn't like him and is just cock-blocking him and preventing him from being with anyone else. Ian plays the rope ladder game and wins a prize, which he gives to Felicia. A hot girl is in line behind them, so with Lance's urging, Ian takes it away from Felicia and gives her the prize instead. The girl is flattered and invites Ian to come watch her dance. They all go and we see the girl's dance troupe doing a really hot and provocative routine. The girl pulls Ian up on stage, and behind him we see that it is an abstinence group. Ian doesn't realize this, and some lady begins to talk. All Ian can focus on is his view of the girls changing back stage. He get a huge hard-on while the woman yells at him and tries to get him to take an abstinence pledge. Fed up, Ian storms out and yells at the girl for tricking him. The girl screams back that she would have given him head. She throws something at him and he ducks, so it hits Felicia in the face.
The three drive Felicia to a dentist because her tooth is chipped. Ian takes care of her. Seeing him hitting on the other girl and how nice he is in general makes Felicia see him in a new light and begin to like him. Ian steps out as the dental procedure begins and goes into a store to buy snacks and some shoes for Felicia. He then talks to Lance about how they should just go home when Felicia storms out of the dentist. The online girl texted Ian about meeting him tonight. Felicia thinks Ian is gross and is so mad that she was falling for him. They fight and Ian decides to just go through with meeting the online girl and having sex.
Somewhere in here they end up hitting an animal while driving. Ian kills it with a tire iron to put it out of its misery, and it doesn't die easily. Upset, Ian throws the tire iron in the air and hits a cop car. They all get taken to jail and Mary (the Amish girl Lance liked) bails them out. She rides along with them for the rest of the trip. Felicia is touched by how much Ian cares for the animal and also finds the shoes that he bought her.
The trio arrive in Nashville, TN and Ian rents a cheesy room with a fireman theme. He get ready to meet the girl when Felicia tries to stop him. She asks him why he is doing this and tells him that if he just wants to have sex in order to lose his virginity he should do it with her because at least she is a friend. Ian tells her he would rather have sex with a stranger than pity sex with her. Felicia leaves because she really likes Ian, but is afraid to tell him the truth. Ian goes to leave soon after, but Rex shows up and is mad Ian stole his car. Rex beats Ian up, but Ian tells Rex he was just trying to have sex with a girl so he didn't turn gay like Rex warned him. Rex lets Ian go with the car, as long as he promises to come straight back.
Ian drives to the Denny's and meets up with the online girl, Ms. Tasty. She strangely doesn't mind that he isn't the hot football stud from the picture. They drive to a remote location and start making out on top of the donut suit. Ian stops and tells Ms. Tasty that he can't do it. He still loves Felicia and he knows that if he goes through with it she won't ever want to be with him. Felicia is hiding in the car and overhears what Ian says. She loves him and is so happy. Just then Ms. Tasty's boyfriend shows up with a gun and Ian realized Ms. Tasty was just using him to steal the car. They take Ian's clothes and go back to the Denny's to wait for the next unsuspecting guy they have lured to show up.
As the car pulls into Denny's, the convenience girl's boyfriend from the beginning come roaring into the parking lot with his truck and slams into the car. Rex sees his car get hit and runs out into the parking lot. Lance and Mary also hear the commotion and stop having sex in their under-the-sea themed room to find out what is going on. They all argue about who hit whose car and who slept with whose boyfriend. Felicia takes the opportunity to sneak out of the car, but Ms. Tasty sees her. Knowing that Felicia overheard Ms. Tasty and the boyfriend's plans to steal more cars and sell them for parts, the boyfriend goes to shoot Felicia. Ian dives into the scene in the donut costume and saved Felicia.
Ian as Senior Donut grabs the gun. He settles things between Lance and the boyfriend by letting the boyfriend punch Lance one time for sleeping with the convenience store girl. He also shoots Ms. Tasty's boyfriend when he tries to grab the gun. Finally the police show up. The police are stupidly confused that Ian is in a donut suit (trying to mace the fake eyes, etc.), but it is eventually straightened out and Ms. Tasty and the boyfriend are arrested.
Felicia, Lance, and Ian drive home, stopping at the Amish community to do chores. While there, Lance decides to stay so he can be with Mary. Felicia and Ian drive back alone. On the way they stop at the shoe tree so that Ian can be impractical and toss away his shoes, showing Felicia that he is the guy for her.
Lance and Mary get married. Rex comes out to his family and brings a boyfriend home for Christmas. Felicia and Ian get together.
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