Reuben Feffer, a cautious actuary at a major life insurance company, is on his honeymoon with his new bride, Lisa Kramer, in the idyllic surroundings of St. Barts. However, his bliss is short-lived when he stumbles upon Lisa in an intimate encounter with Claude, a charming French scuba instructor. Heartbroken and abandoned, Lisa confesses her love for Claude and opts to stay on the island with him, leaving Reuben to return alone to his life in New York.
Back home, Reuben struggles to rebuild his shattered life. During a visit to an art gallery with his humorous friend, Sandy Lyle, he unexpectedly reconnects with an old classmate, Polly Prince. Intrigued by Polly, Reuben invites her out, and she extends an invitation for dinner at a Moroccan restaurant. Despite his battle with irritable bowel syndrome, he agrees. The night takes a turn for the worse when he accidentally clogs her toilet. Fortunately, Polly gives him another chance, and they hit the dance floor together.
As Reuben faces the challenges of stepping outside his comfort zone, he finds himself at a salsa club where Polly dances exuberantly with her friend Javier. Feeling out of place, Reuben opens up to Polly about his aversion to spicy food and risky activities. Nonetheless, his feelings deepen, culminating in an intimate night together.
Their relationship progresses, pushing Reuben to embrace new experiences, guided by both Polly’s adventurous spirit and the persistent CEO, Leland Van Lew. When Reuben requests dance lessons from Javier, he surprises Polly with his newfound salsa skills on their next outing.
Just as Reuben begins to find his footing with Polly, Lisa returns, reigniting old feelings and complications. Polly grows apprehensive when Reuben refers to her as his girlfriend. Torn between the thrill-seeking Polly and the comfortable familiarity of Lisa, Reuben turns to an insurance program to analyze his situation. Although rife with blunders, the data suggests that Polly is, in fact, the less risky choice for him.
A sailing trip organized by Van Lew leads to an unexpected confrontation between Reuben and Polly during a storm. Discovering Reuben's risk assessment, Polly feels betrayed. She ultimately declines his proposal to move in together, suggesting that he might be better off returning to Lisa.
Deeply troubled by the potential loss of Polly, Reuben invites Lisa to an art show where he learns that Polly is about to leave New York for good. Simultaneously, he receives an urgent work call to present his risk analysis on Leland. Motivated by a heartfelt speech from his father, Irving, to Sandy about embracing the present, Reuben races to Polly's apartment in a desperate attempt to stop her departure.
In a moment of spontaneity, Reuben endeavors to prove his willingness to take risks by eating food off the ground. This bold act finally convinces Polly of their compatibility, leading to the start of their relationship, albeit with a mutual understanding of taking it slow.
Fast forward a year, we find Reuben and Polly enjoying their vacation once more on the stunning beaches of St. Barts. As Reuben embraces life more freely, Polly begins to find her comfort in commitment. They unexpectedly cross paths with Claude, who, rather than harboring anger, thanks Reuben for inadvertently setting in motion the events that brought him to this point. With renewed confidence, Reuben joins Polly in the water, ready to embrace whatever lies ahead.
