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Centerville High School student Henry Aldrich is determined to graduate with honors so that he will be eligible to inherit $5,000 from his uncle and attend Princeton University. When Henry confides to his mother that principal Bradley, who is also his botany teacher, has been racking up demerits for him even though he does not deserve them, and is thereby sabotaging his chances at a college education, Mrs. Aldrich declares that it is only because Bradley is an unhappy bachelor. Henry seeks his father's Sam's advice, but the attorney is too involved in a dispute with Senator Tom Caldicott, a former college chum, over the construction of a dam, to see his son. When Henry learns that his best friend Dizzy Steven's uncle met his new wife through a personal advertisement, Henry is inspired to find Bradley a wife. He writes to the three women whose letters Dizzy's uncle discarded, and because the yearbook photograph of Bradley is unflattering, Henry sends a photograph of a man he believes to be his deceased uncle. Henry is appalled when he sees a picture of the same man in the newspaper and learns that he is Caldicott, who is arriving that day to investigate Sam's dam proposal. Dizzy and Henry meet widow Mrs. Terwilliger at the train station with flowers and candy and tell her that her "Prince Charming," as they had signed the letter, is away on a secret government mission. When Mrs. Terwilliger, who signed her letter "Blue Eyes," sees Caldicott emerge from the train, she rushes up and embraces him, and after pushing her away, Caldicott avers that someone is attempting to discredit him. To the boys's relief, Mrs. Terwilliger accepts their excuse that Caldicott is working undercover. Later, Henry tries to fix Mrs. Terwilliger and Bradley up on a picnic, but the results are disastrous as Henry spills food and water on Bradley, and then urges him to row Mrs. Terwilliger to the other side of the lake, after he has pulled the plug in the rowboat. When the boat sinks, Mrs. Terwilliger rescues Bradley, who cannot swim, and Bradley's opinion of Henry plummets further. After Henry's girl friend Phyllis Michael admits that Henry purposely pulled the plug and was trying to get Bradley married, Bradley appears to reconsider the situation, and takes Mrs. Terwilliger out to dinner. Henry makes a deal with restaurateur Tony to provide romantic enticements for Bradley, and is mortified when Caldicott comes into the restaurant. After a foiled attempt at getting Caldicott to leave by putting soap flakes into the parmesan shaker, Henry is upset when he sees Mrs. Terwilliger flirting with Caldicott. Caldicott, determined to find out if she is trying to undermine his investigation, interrupts her dinner with Bradley, who was just about to thank her for saving his life. Mrs. Terwilliger is delighted by the attentions of the man she presumes is her intended husband. Caldicott presumes that Mrs. Terwilliger's flirtations are a set-up by Sam, and the next day, Caldicott, followed by reporters, angrily reproaches Sam for playing a "badger game." He is further incensed when "Wild Rose," Henry's second respondent, walks up to him and kisses him. Henry pulls Wild Rose away and tells her the truth, and she insists that he give her $500 for expenses or she will reveal his deception. Worried about his father, Henry goes to Caldicott's hotel room and confesses the truth, but Caldicott disbelieves him. Sam, meanwhile, treats Wild Rose to dinner and learns that his son is behind all the trouble. Sam plans on sending Henry away to his grandmother's house, but the entire family is subpoenaed to appear at the chamber of commerce as part of the state senatorial investigation. Sam is outraged when Caldicott makes public accusations that imply that Sam bought the land around the lake for his own purposes, rather than to protect the township, as Sam claims. The Aldriches are all surprised, however, when they discover that instead of walking into a trial, they are the guests of honor at a banquet at which Caldicott praises Sam for his honesty. Sam, seeing that Caldicott has been playing a practical joke, makes peace with his old college friend, and Caldicott announces his marriage to Mrs. Terwilliger. Wild Rose shows Henry the diamond bracelet that Caldicott gave her as a consolation gift, and Henry is shocked when Phyllis explains that Bradley has reunited with his wife, from whom he has been separated for ten years, and that he was inspired by Henry's attempts at matchmaking. Bradley assures Henry that he has erased all the demerits from his record. Just as Henry's troubles seem to vanish, respondent number three walks in and embraces Caldicott, and a chagrined Henry runs out of the room as Caldicott calls his name.