The story begins with Christian Black, a character portrayed by Marlon Wayans, engaging in his daily mischief. His antics include snatching a woman's purse, pilfering an expensive suit, and commandeering a sleek sports car. Subsequently, he arrives at his workplace, where he is quizzed by college student Hannah Steale, played by Kali Hawk. Her comically intrusive questions, scripted by her unscrupulous roommate Kateesha (played by Jenny Zigrino), revolve around Christian's income and his sexual orientation. Christian cheekily mentions he made his fortune in drug dealing and that he has tried something "gay" only once. Just as Hannah exits, her head gets ensnared in the elevator doors, setting the stage for a series of awkward events.
Later, Hannah hangs out with her friend Jesse, who harbors clear romantic intentions toward her. He volunteers to assist Christian with a photoshoot that features the infamous Kim Kardashian wine glass pose. Their paths cross when Christian spots Hannah at the hardware store, where she humorously pretends to perform inappropriate acts with a screwdriver.
That night, while out with Jesse and Kateesha at a bar, Hannah indulges a bit too heavily in drinks, leading to a tense moment when Jesse attempts to take advantage of her in her vulnerable state. Luckily, Christian intervenes, but not without suffering a beating from Jesse. Meanwhile, Kateesha catches the eye of Christian's brother Eli, also known as Weekday due to his eccentric hairstyle reminiscent of The Weeknd.
In a turn of events, Hannah wakes up in Christian's apartment wearing unfamiliar clothes. He openly admits to having undressed and redressed her while sharing a peculiar breakfast—a piece of toast he licked repeatedly. In a passionate flurry, they make out in the elevator, only to eventually stumble upon Eli and Kateesha caught in a compromising position, much to their shock.
As their relationship develops, Christian discovers that Hannah is still a virgin, a point of surprise given her self-image. This inevitably leads to them becoming intimate, although it turns out to be a brief encounter. Afterward, Christian proposes exploring some unconventional aspects of their relationship, presenting her with a contract for S&M activities. Surprisingly, Hannah seems open to various experiences that Christian introduces.
Then, Hannah meets Christian's adoptive parents Gary and Claire, alongside his adopted sister Mai. Their interactions are marred by racially insensitive meal choices, which brings out the film's satirical edge. As her intrigue deepens regarding Christian's background, she learns about his awkward first sexual experience with the elderly Mrs. Robinson, which never quite went as planned.
As their connection intensifies, the two experiment with different sexual dynamics, leading to a striking role reversal where Hannah dominates Christian, resulting in humorous yet unexpected scenes. Following a heated bout of dominance, Christian finds himself in a vulnerable position, prompting Hannah to declare that he is incapable of love.
In a climactic resolution, Christian chases after Hannah, professing his feelings for her. They share a kiss, and as he promises her a getaway, she whimsically anticipates a luxurious trip on his private jet. Instead, they find themselves crammed in coach on a noisy flight, sitting next to a man who unfortunately becomes ill, painting a comical picture of their rom-com journey.
