Frankie is a 34-year-old Brooklyn resident working for a non-profit that assists small businesses while simultaneously pursuing her MBA. She acts as the maid of honor for her best friend's destination wedding, placing her in direct contact with wealthy socialites she distrusts. Proud of her working-class background, she relies on a strong work ethic and refuses to let others intimidate her financially or socially.

Aiden is the 40-year-old chief operating officer of his family's multi-billion-dollar enterprise. A Yale graduate, he holds a reputation as Manhattan's most eligible bachelor, though he keeps his romantic relationships strictly short-term. He operates with a cool, aloof demeanor and expects others to accommodate his needs, yet he suffers from debilitating stress migraines that leave him physically vulnerable.

Pru is Frankie's best friend from their time as students at New York University. Despite her access to a higher social class, she values Frankie's friendship immensely and acts as a bridge between Frankie's working-class roots and the wealthy world of the wedding party. She offers steady support and blunt advice to her fiercely independent friend.

Elliot is Aiden's half-brother and a lazy, self-serving participant in the Kilbourn family business. He leverages blackmail and corporate sabotage to get his way, frequently casting himself as a victim to win their father's favor. He lacks genuine loyalty to his family members and views business operations strictly as a means to personal enrichment.

Chip is the groom in the upcoming destination wedding in Barbados. He acts as Aiden's only close friend, providing a cheerful, outgoing counterpoint to Aiden's serious corporate demeanor. His upcoming marriage to Pru serves as the catalyst for bringing the vastly different social circles together.

Marco is Frankie's older brother who manages the Baranski family's Brooklyn deli. He is happily married to a woman named Rachel and actively participates in the loud, affectionate dynamic of his household. He fiercely protects his sister and offers unsolicited but well-meaning advice to anyone trying to date her.

Gio is Frankie's brother, working alongside Marco at the family deli. Like his older brother, he embodies the relaxed, straightforward loyalty of the Baranski family. He uses humor to test newcomers to their home and remains constantly watchful over his sister's well-being.

May is Frankie's mother, a highly vocal and opinionated woman who deeply loves her children. She openly expresses her concerns about social class differences and frequently pressures her daughter about starting a family. She rules the Baranski household, quick to physically cuff her sons on the head for making rude gestures.

Hugo is Frankie's father, a working-class man who founded the family's sandwich deli. He is quieter than his wife but shares her deep investment in their children's happiness. He enjoys evaluating his daughter's suitors over drinks and sports games.

Ferris is Aiden and Elliot's father, the patriarch of the wealthy Kilbourn family. He is a demanding figure who misuses the concept of family loyalty to manipulate his sons into executing his business agendas. He views romantic partners strictly through the lens of social suitability and corporate advantage.

Cecily is Aiden's mother, who came from a working-class background before marrying into the Kilbourn family. Unlike her ex-husband's current social circle, she remains friendly, welcoming, and down-to-earth. She provides Aiden with his only source of genuine maternal warmth.

Jacqueline is Aiden's stepmother and Ferris's current wife. She is deeply entrenched in high-society snobbery and looks down on anyone from a working-class background. She uses mean-spirited gossip and condescension as social weapons at charity events.

Margeaux is a wealthy, entitled bridesmaid in Pru's wedding party. She treats service workers poorly, argues with other guests over spilled drinks, and consistently tries to undermine Frankie's confidence with petty insults.

Antonio is a local teenager in Barbados who provides essential transportation and geographic knowledge to the wedding guests. Operating a dune buggy in his school uniform, he proves highly resourceful in finding the island's hidden locations and local hangouts.

Papi is a local criminal hired by an anonymous client to execute a kidnapping in Barbados. He frequents specific rum bars on the island and proves highly susceptible to cash bribes and visual distractions.

Brenda is Frankie's boss at the small business development center. She is supportive of Frankie's professional ambitions and personal life, managing an office that frequently struggles with funding issues.

Rachel is Marco's pregnant wife. She is a part of the close-knit Baranski family and offers advice to her husband when he tries to comfort his upset sister.