When Jackie Kennedy decides it's time for her son, John F. Kennedy Jr., to settle down, she arranges an engagement with Betsy Vanderbilt, the rebellious heiress of one of America's wealthiest families. Neither John nor Betsy is thrilled with the idea of becoming pawns in their families' high-society games, and they vow to make the engagement as difficult as possible. But as they are forced to navigate a whirlwind of public appearances, staged romance, and elaborate family schemes, something unexpected happens - their fake romance begins to feel a little too real. Betsy is drawn to John's charm and the vulnerability he hides behind his playboy persona, while John is captivated by Betsy's wit, confidence, and refusal to play by anyone's rules. From heated arguments to stolen moments under the stars, they find themselves falling for each other in ways neither of them expected. But with their families pushing them toward a union they never wanted, can they trust their growing feelings? Or are they simply getting caught up in a game they never chose to play? In a world where appearances are everything, can two people find the courage to embrace what's real?