Hannah Steele, a shy and awkward college student, agrees to interview the wealthy and enigmatic entrepreneur Christian Black as a favor to her roommate. During their meeting, Hannah is both intimidated and intrigued by Christian's confident and controlling demeanor. Despite her reservations, she finds herself drawn to him and soon learns about his unconventional tastes and peculiarities. Christian reciprocates her interest but makes it clear that he desires a relationship on his own strict terms, which involves a peculiar contract outlining specific conditions and limitations.

As their relationship develops, Hannah struggles to keep up with Christian's demanding preferences while attempting to stay true to herself. The pair navigates a series of comedic and often embarrassing adventures that test Hannah's boundaries and patience. Throughout their time together, Hannah learns more about Christian's troubled past and attempts to understand the reasons behind his behavior. Their story unfolds with humorous twists and turns, leading Hannah to question whether she can handle the dynamic of their unusual romance.