The film opens with Tori (Cherami Leigh), a former high school student, at a party, reflecting on her disdain for high school before being unexpectedly vomited on by another reveler. The narrative shifts back a few hours to the airport, where she is set to reunite with her family, which includes her parents, Kasey Daley and John Yost, as well as her blind sister Lisa Schwartz. Upon her arrival, she jokingly asks a homeless man if he'd like to "switch lives," to which he sarcastically replies that he would prefer "to eat his own sh*t." Upon meeting her family, Tori's sister Marissa excitedly announces her engagement, setting the stage for family tensions.
Meanwhile, at the airport, another high school alumnus, Scott (Shane Dawson), is met by his girlfriend Heather (Jorie Kosel), who drags him into a men’s restroom stall. There, her demands escalate, leading to a dramatic breakup after she bursts into tears.
Joel (Drew Monson), another former classmate, makes his way back to high school to visit his long-time crush, Janie (Michelle Vientimilla), who just so happens to be Scott's sister. In an unfortunate slip, Joel reveals to Janie that her father, Bill Lang, is set to close his store, prompting a heated reaction from both siblings, who are less than pleased about their father's decision to move to Florida for a new romantic involvement.
Desiring to escape the gloom at home, Tori joins Joel at a party. While attempting to charm Janie, he accidentally spills her drink, which leads them to the restroom for a brief detour. During this moment, they uncover Janie's academic struggles; Joel generously offers his tutoring services, which she gratefully accepts. However, the party takes a turn for the worse for Tori when another partygoer vomits on her, forcing her to leave early. Fatefully, Tori inadvertently runs into Scott with her car, leading to a mix of tension and humor as he recognizes her as "Tori the Whorie." After some banter, Scott requests a ride to Heather's, whom he is desperately trying to win back. This encounter quickly turns physical when they share an unexpected kiss, highlighted by Tori's cheeky comment about her stash of condoms.
Fast forward to Thanksgiving, where families celebrate together. Scott chooses to leave his own family's gathering to seek out Tori. He interrogates her about their connection from the night before. After she brushes him off, Tori's mother invites Scott inside to join them in a competitive game of Dance Central. Scott proposes a wager: if he wins, Tori must kiss him. When Tori fires back with insults, Scott lets her take the victory, resulting in a farewell, seemingly for good.
The following day, chance brings Tori back into contact with Scott during a shopping outing, prompting an awkward yet comical encounter. When Tori accuses him of stalking her, Scott reveals his true intentions were captured via candid photos during Black Friday shopping, creating a more playful atmosphere. Tori expresses her insecurity about her relationship history, stating she didn’t sleep with the “cool guy,” but rather with a “formerly cool guy who’s actually a big dork.” As Scott struggles to recall any "cool" actions from his life since graduation, Tori invites him to step out of his comfort zone by completing her "F*ck it list," beginning with some outrageous dares.
Highlights from their mischievous adventures include attempts to engage in silly antics: Scott humorously putting a cucumber down his pants and Tori stuffing a watermelon under her shirt during a grocery run, leading to an unexpected comment from the cashier. Their antics culminate with Scott fainting after a piercing escapade initiated by Tori. Meanwhile, chaos ensues as Joel tries to impress Janie by renting a party bus, but his intentions quickly blur toward less honorable pursuits.
The emotional stakes rise as Tori shares a brownie with Scott, claiming it to be a pot brownie. In a moment of honesty, she confesses it was merely a regular treat, triggering a back-and-forth conversation about their previous mishaps. They both open up, and Scott takes Tori on a surprise trip to an empty football stadium, aiming for a romantic moment interrupted by Tori’s playful tackle.
Joel sets up a heartfelt dance with Janie following their dinner at a fancy restaurant; however, her clarity leads her to leave him, sensing his manipulative charm. In an important confrontation, Tori finds Scott at her sister’s engagement party wielding a razor and shaving his head to demonstrate his commitment to changing his ways. Their reconciliation leads to a sweet kiss, marking a new chapter as Tori assists him with his freshly shaved locks.
As the movie draws to a close, we see Tori reflecting on her memories with Scott while at the airport, paralleling Scott staring at a picture of them from Black Friday. The film concludes with Scott sending Tori a playful Snapchat message: > “See you Christmas.”
