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In 1884, middle-aged widow Dolly "Gallagher" Levi ekes out a living as a matchmaker, thereby indulging her passion for "rearranging" other people's lives. One morning, she goes from New York City up to Yonkers to visit wealthy merchant Horace Vandergelder, who desires to remarry after many years as a widower. Although Dolly has introduced Horace to Irene Molloy, a much-younger milliner, she intends to marry Horace herself. Dolly goes to Horace's general store, at which he employs the overworked and underappreciated Cornelius Hackl and Cornelius' young assistant, Barnaby Tucker. There, Horace confides in Dolly that he intends to propose to Irene that afternoon in New York, and to distract him, Dolly shows him a photograph of a well-endowed young woman. Concocting a fake name, Ernestina Simple, Dolly describes the girl's many virtues, and Horace agrees to meet her at the lush Harmonia Dinner Gardens. Horace still insists on seeing Irene, however, and leaves the store after refusing to give Cornelius and Barnaby even a single night off. Frustrated that life is passing him by, Cornelius tells Barnaby that they are also going to New York, and will not return until they have had a good meal, been in danger, almost been arrested and kissed a girl. After blowing up two rows of canned tomatoes, so that the resulting odor will force them to close the store, Cornelius and Barnaby set off on their adventure, even though they have only ten dollars. A few hours later, after fulfilling most of their requirements, Cornelius and Barnaby lament the fact that they have not even met any girls. They happen by Irene's shop, and when Cornelius is struck by her beauty, he decides to impress her by pretending to be rich. Meanwhile, inside the shop, Irene's timid friend, Minnie Fay, asks Irene if she is serious about marrying Horace. Irene replies yes, stating that she never meets any other men and hates making hats. They are interrupted by the arrival of Barnaby and Cornelius, with whom Irene shares an immediate attraction. As Cornelius and Irene flirt, he describes Yonkers' beauty. Barnaby spots Horace and Dolly coming, however, and Cornelius, telling Irene that he will explain later, hides in the cupboard while Barnaby dives under a table. Hoping to give the young men time to escape, Irene takes Horace and Dolly into her workroom, but Cornelius is determined to stay. Dolly catches Cornelius and Barnaby while they are out of their hiding places, and Cornelius confesses his feelings for Irene to her. As they are talking, Irene asks Horace if he has heard of her other friend from Yonkers, Cornelius, and Horace laughingly reveals that Cornelius is merely a clerk, not a wealthy man. Dolly scoffs, stating that Cornelius leads a double life and is not only rich, but a devil-may-care adventurer famous for pulling practical jokes. Horace's stunned silence is interrupted by a series of sneezes from Cornelius, but Irene succeeds in keeping his and Barnaby's identities disguised. Scandalized that Irene is hiding men in her shop, Horace breaks off their relationship and storms out. Determined to enjoy herself now that she is in "disgrace," Irene orders Cornelius and Barnaby to take her and Minnie to dinner at Harmonia Gardens, and Cornelius, desperate to please her, agrees. An hour later, the boys escort the girls to the lavish restaurant, where they take a private dining room. Even though they are worried about their lack of funds, Cornelius and Barnaby get caught up in the excitement of their adventure and enjoy the girls's company. Because the curtains to their room are closed, the boys do not see as Horace enters and takes the private room next to theirs. As he arrives, Horace accidentally drops his wallet, but does not notice. Soon after, however, Barnaby spots Horace and alerts Cornelius, who panics. Dolly arrives and joins Horace, calming his impatience to meet Ernestina with an assurance that she will come soon. They are then joined by Irishman Malachi Stack, whom Horace hired that morning. Malachi asks Horace for an advance on his salary, and after Horace gives him a dollar, Malachi finds Horace's fallen wallet. Malachi spots Cornelius, who is worriedly peering out of his room, and assumes that the wallet belongs to him. When Malachi presents the cash-heavy wallet to him, Cornelius is overjoyed, while in the next room, Dolly receives a telegram, supposedly from Ernestina, saying that she cannot come because she has married someone else. Horace is outraged, but Dolly insists that they eat the lavish meal she has ordered, and intimates that Horace really wants to marry her, but that she is not interested. Meanwhile, Cornelius decides that he cannot keep lying to Irene about who he really is and, after leaving her enough money for the bill, prepares to leave with Barnaby, supposedly to buy the girls a present. Because they spot Horace and Dolly dancing, the boys are forced to don the girls's coats and veiled hats. They get caught up in the dancing, and Horace is soon waltzing with Barnaby, while Cornelius dances with Dolly and slips Horace's wallet into her purse. After their escape, Cornelius sends a note to Irene that he will not be returning, but assuring her of his feelings for her. Horace, having realized that "Ernestina" was merely one of Dolly's schemes, is happy to see Irene, whom Minnie is consoling, and attempts to renew their engagement. Irene agrees to go to Yonkers with him the following morning, although she is really interested in finding Cornelius. As they are leaving, Horace discovers that he has lost his wallet, and Irene pays her bill and his, proving to Horace that while money is valuable, friends are even more so. A few moments later, Dolly goes by Irene's shop and there discovers the boys, who are attempting to return Irene and Minnie's clothes. Dolly tells the boys she has a plan, then goes with them back to Yonkers. The next morning, Horace escorts Irene and Minnie to his store, where he is aghast to find the burst tomato cans and learn that Cornelius and Barnaby are missing. He then sees Cornelius, Barnaby and Dolly across the street as they are tacking up a banner announcing the opening of their own store. In reality, they had only enough money to rent the vacant building for one day and are hoping that the threat of losing them will teach Horace how much they mean to him. Thrilled to be reunited with Cornelius, Irene forgives him for his inadvertent subterfuge, and they kiss. With Irene and Minnie making plans to join Cornelius and Dolly's shop, Horace shushes them all with an announcement that their scheme has worked and he repents his penny-pinching ways. After Dolly coaxes Horace into making Cornelius a partner in his store, Horace proposes marriage to Dolly and she graciously accepts. With their problems solved, the friends ponder the moral of their story, with Barnaby offering that everyone should take a day off now and then, and Cornelius hoping that everyone's lives have the right mixture of adventure and sitting quietly at home.