During the opening credits, Paul Benton and Warren Palmer perform a lively duet, "I'd Rather Be Rich." We then meet Cynthia Dulaine sitting at a nightclub table while Warren Palmer croons "It Had To Be You." Philip Dulaine is introduced as the founder and CEO of Dulaine Enterprises, and Cynthia is his closest surviving relative and heir. He confides that his dying wish is for her to find the right man to marry, and she proudly tells him about her fiancé, the kind, considerate, and handsome Warren Palmer, whom Philip has never met. He urges a meeting with the man as soon as possible, hoping to see the match blessed before he passes.
Stuck in Boston because of airport difficulties, Warren cannot be there in person. Desperate to give her grandfather a happier illusion of his future, Cynthia recruits a stranger to pose as Warren for an introduction to Philip. That man is Paul Benton, an inventor who has developed a heat-proof paint and seeks a chance to secure a NASA contract through Philip’s company. Benton agrees to the ruse, and the deception goes off smoothly, with Philip visibly touched by the sight of the couple together—especially when Benton makes the two kiss and Cynthia kicks off her shoes just as her grandmother did when she and Philip shared a kiss.
Philip explains that Dulaine Enterprises faces a potential hostile takeover and urges Cynthia to join a board meeting to help safeguard the company. He insists she bring her fiancé along, a demand that sets the stage for further complications. The first board encounter is rocky until Benton announces that Cynthia is willing to invest her own money into the business, a move that mollifies the directors. Yet Cynthia later confronts Benton for acting without consulting her first. Still, she helps him by directing him to the best person at the company to test his invention for NASA.
Meanwhile, Philip unexpectedly recovers and returns to relative health, leading to a playful cat-and-mouse game with his nurse as she tries to keep him from smoking the many cigars hidden around the mansion. The recovering patriarch grows fond of Benton and begins to see him as the right man for Cynthia, but the mood shifts when he overhears Cynthia tell Benton that the real Warren Palmer is arriving that afternoon and that Benton’s hold on the situation may be temporary.
Rather than letting the truth surface, Philip continues to pretend to be near death, coughing and feigning weakness whenever Cynthia tries to reveal the real fiancé. Benton uses this ruse to stay close, hoping to safeguard Cynthia’s happiness and convinced that Benton might truly be the one she loves—the signal is clear to him every time she can’t keep her shoes on around him.
In due course, the real Warren Palmer arrives at the Dulaine mansion and is reluctantly asked to pose as Paul Benton. Benton, who has fallen for Cynthia, does his best to disrupt late-night romantic plans and even booby-traps a planned getaway. In the car, Palmer serenades Cynthia with the song "Almost There," but the couple’s attempt at privacy is thwarted by Benton, forcing them to cut the rendezvous short.
Philip then arranges a shareholders’ dinner and dance, pushing the two couples into closer contact. The evening ends with a visible scramble on the mansion lawn as the two rivals spar—both in word and in action—before the truth is finally laid bare. When the moment comes, Philip reveals that he is no longer dying, and that Cynthia’s recent foot problems, much like her grandmother’s condition, point to which man she truly loves.
After a sequence of further amusing misunderstandings and heartwarming moments, Cynthia ends her engagement with Warren Palmer and chooses Paul Benton, signaling a new union built on genuine connection rather than deceptions. The film closes on a hopeful note, with the promise of a future shaped by honesty, humor, and the surprising ways love can bloom under the most unlikely circumstances.
