Four male teenagers from New Orleans, Louisiana - Matt Bennett, Zack Pearlman, Jacob, and Justin - buy a bong and make a pact to only use it in celebration of their first sexual encounters. As they start to lose their virginity, Matt finds himself as the last one standing. He is the adopted brother of Zack, having lost his mother to cancer at just nine years old, while his father struggles with drug issues, playing a minimal role in his life. Matt has been dating Nicole for nearly two years, and together they plan to mark their second anniversary by becoming intimate for the first time.
Zack, with an eye for the dramatic, decides to record the entire experience, envisioning it as a documentary. However, just as Matt is gearing up for the momentous night, he receives devastating news: Nicole has been unfaithful, cheating on him with college frat boy Harry. Zack is determined to get to the bottom of it and goes searching for Harry to confirm the betrayal. When Matt and his friends conclude that the worst has indeed happened, they alter their plan for the big night. Zack suggests that Matt should go ahead and have sex with Nicole but break up with her immediately thereafter, believing this twist would make for compelling footage in his documentary.
Arrangements are made for Matt to meet Nicole at a hotel. Yet, when Nicole realizes they are being filmed from an adjoining room, she erupts in anger and reluctantly admits to Matt that she didn't go very far with Harry; it was only an incident of heavy petting. Just then, her father arrives, forcibly takes her away, and shoves Matt into a bush following their breakup. This embarrassing turn of events soon hits YouTube and unexpectedly gains traction. Amidst the chaos, a woman named Becca sees the viral video and feels sympathy for Matt. She reaches out with a video response, expressing interest in being his first experience, but with a rather peculiar request that he procure an expensive suit for their date.
With the encouragement of Zack, Matt thinks back to the large sum of money his mother left him. However, when he discovers that his father had drained those funds for his own drug problems, Matt becomes infuriated and confronts his father, who shows no intention of reimbursing him. After a wild night of drinking and camping with Krysta Rodriguez, who unsuccessfully attempts to seduce him, Matt returns home and hatches a plan to steal the suit he needs.
After finally meeting Becca, he learns she has a child and receives a note insisting he must be completely shaved, leading to a humorous scene where Zack assists him in this requirement. On the day of their date, Matt learns that filming is off-limits and that he must practice on a blow-up doll utilized for instructional purposes. Becca later reveals on her video blog that her identity is not really "Becca" and that her research involves studying male behavior. Disheartened by this unexpected information, and the ensuing embarrassment from the video of him with the doll, Matt retreats to his room for two weeks.
Determined to help their friend move past his embarrassment, the boys devise a plan for Matt to have an encounter with his beloved porn star, Sunny Leone. They manage to contact her, and after raising the necessary funds, they use Jacob’s military enlistment as a cover to get Matt out. At the strip club, Sunny reveals she has changed her mind about their encounter and encourages Matt to find love instead. After a brief moment alone with her, Matt emerges with a new perspective and finds Nicole at a party, where they resolve their past issues and finally have sex. With the bong in hand, the boys toast to Matt's newfound experience in losing his virginity.
