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Lynn Crandall travels by train with her younger sister Peggy from New York to Chicago, where Lynn is to marry her wealthy friend, Harvey Jones. Lynn must marry by her twenty-fourth birthday in order to gain a $95,000 inheritance, as willed to her by her late uncle, George Crandall. On the train, the sisters meet soldiers Tony Smith and Alexander Archibald O'Reilly, better known as Squirt. Peggy, who is against Lynn's marriage to Harvey, plots to bring Lynn and Tony together by pretending to have the measles. The conductor has Peggy examined by Doc Webster, a "jack of all trades," who declares that she has German measles and insists that Peggy's pullman car be quarantined from the rest of the train. Afraid of losing her inheritance, Lynn, whose birthday is fast approaching, connives to marry Tony, and tricks him into a wedding. Upon arriving in Chicago, Lynn and Peggy inform Harvey and their aunt, Harriet Crandall, that Lynn has married Tony. An upset Tony then learns of Lynn's true marital intentions, and returns to his Army base. Later, Lynn learns that she cannot spend any of her inheritance unless her checks are co-signed by her husband. Acting upon Peggy's suggestion, Tony refuses to cooperate with Lynn's lawyer, so Lynn is forced to meet with her husband during his twelve-hour furlough. When he refuses to sign any check for an amount over ten dollars, Lynn takes Tony to her uncle's cabin, which is affectionately known as "George's Crazyhouse." Learning of Lynn's whereabouts, Harvey rushes up to the cabin with painter Goreni, who immediately seeks Lynn's art patronage. Tony, however, steadfastly refuses to sign any of Lynn's checks and returns to the Army base. Later, Harriet invites the soldiers to a party at her home, during which Tony agrees to an annulment if Lynn places her inheritance in a trust, which would protect her from people like Goreni. Lynn agrees, but the judge hearing their case has Tony sing to Lynn to see if they are really in love. After his ballad, Tony and Lynn realize that they are truly in love and decide to start their marriage in earnest.