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Reuben Feffer is a cautious, risk-averse risk analyst living in New York City, whose entire existence is defined by probability charts and insurance policies. His meticulously planned world shatters during his honeymoon when his new bride, Lisa, cheats on him with a scuba instructor on the very first day. Devastated and humiliated, Reuben returns home alone, retreating into his safe shell of spreadsheets and sterile routines.A short time later, at a mundane art gallery opening, Reuben unexpectedly crosses paths with Polly Prince, a free-spirited, chaotic former high school classmate. Unlike Reuben, Polly lives entirely in the moment, constantly changing jobs, keeping a blind pet ferret named Rodolfo, and embracing chaos with open arms. Desperate for a spark to jolt him out of his post-divorce depression, Reuben impulsively asks Polly out on a date, initiating a passionate and whirlwind romance that challenges every single one of his deeply ingrained philosophies.As their relationship progresses, Reuben is forced to step drastically out of his comfort zone. He endures intensely uncomfortable situations, such as eating wildly exotic, spicy Moroccan food that wreaks havoc on his irritable bowel syndrome, salsa dancing in dimly lit clubs, and meeting Polly's eccentric group of friends. Despite his anxiety and initial reservations, Reuben finds himself genuinely falling for Polly's vibrant energy and infectious zest for life.However, complications soon arise. Polly’s commitment-phobic nature clashes with Reuben's desperate need for stability and security. Polly confesses she is terrified of traditional domesticity and plans to move away soon, fearing that Reuben wants to change her into someone she is not. Compounding his stress, Reuben’s estranged wife Lisa suddenly re-enters the picture, begging for a second chance and promising she has changed. Confused and torn between the comfort of his predictable past and the thrilling uncertainty of his future, Reuben retreats to his old safety nets.Realizing he cannot live half-heartedly, Reuben makes a grand gesture to win Polly back. He tracks her down and takes a massive, uncharacteristic leap of faith by jumping into the air off a high ledge into a swimming pool—just as Polly once urged him to do—symbolizing his willingness to embrace life's risks. Touched by his profound transformation and willingness to let go of control, Polly reciprocates his love. The film culminates with the couple happily committing to each other, proving that sometimes the greatest risk in life is refusing to take one at all.