In the late 1800s, Miss Pilgrim, a young stenographer, or typewriter, becomes the first female employee at a Boston shipping office. Although the men object to her at first, she soon charms them all, especially the handsome young head of the company. Their romance gets sidetracked when she becomes involved in the Women's Suffrage movement.

In 1874, at the Packard Business College in New York, Cynthia Pilgrim is the top student of the first graduating class of "typewriters." The Remington Co., maker of the new typewriting machines, has promised each graduate a job, and lots are drawn for the positions. Cynthia lands a job in Boston with the Pritchard Shipping Co. Upon arriving there, she encounters an office filled with men, tobacco smoke and a particularly unwelcoming office manager, Mr. Saxon. When Cynthia introduces herself to the young co-owner of the company, John Pritchard, he tells her that he was under the impression that all expert "type writers" were men and it is his policy to hire only men. Cynthia tells him that he is very old-fashioned, and that she wants an opportunity to prove that women are just as efficient as men. John is unwavering in his resolve and offers Cynthia her return fare to New York. As Cynthia complains to Mr. Saxon, Alice, John's aunt, arrives in the office and becomes involved in the situation. An ardent suffragette, Alice has controlling interest in the company and insists to John that Cynthia be given a chance. Cynthia starts work and soon charms the male clerks. After being rebuffed by two snobbish landladies, Cynthia finally finds lodging at Catherine Dennison's house, where she joins an eclectic group of "outcasts" who despise Boston and its mores. Her companions include Leander Woolsey, a poet; Michael Michael, a painter; Herbert Jothan, a musician; and Viola Simmons, a lady who is rewriting the dictionary to assign new meanings to words. Aunt Alice invites Cynthia to attend a suffragette meeting, but Cynthia considers that the wrong approach; she became a typist to show that women can do men's work, and believes that if equality can be achieved in various fields, suffrage will be a natural conclusion. Alice feels that Cynthia is just what the movement needs. John, on the other hand, still thinks that a woman's place is at home. John invites Cynthia to dinner but, remembering her business college training, she declines to socialize with her employer. John does, however, escort her to one of Alice's rallies, where she is an immediate hit. Later, she does permit John to take her to supper at the Parker House. A few days pass and Cynthia receives a letter from John's mother inviting her to dine with them on the evening of a Regimental Ball. Cynthia feels that Mrs. Pritchard and her social circle will probably be terrible snobs. Her rooming house companions then give her some coaching on how to "behave" and she practices the delivery of insulting remarks. However, John's socialite mother turns out to be not at all snobbish, admires Cynthia and encourages her to keep working. Mrs. Pritchard has even bought a typewriting machine. She tells John he would be an idiot to lose Cynthia but he informs her that he has competition, the Boston Chapter of the New England Womens' Suffrage League. The courtship continues, however, and John and Cynthia become engaged. Later, when he objects to her continued involvement in the suffrage movement, Cynthia says that in the past three months, she has persuaded over four hundred women to go out to work, and insists that she cannot suddenly abandon the cause. John and Cynthia break their engagement and she is replaced in the office by, in rapid succession, three male and three female typists from a new school in Boston. Even grumpy Mr. Saxon admits to missing Cynthia and wants John to accompany him to the school to select yet another candidate. When John is asked by a school official if he has any objection to employing a married woman, he replies that he has come to the conclusion that women are perfectly entitled to work if they want to. Becoming suspicious of the nature of the school's requirements for employers, John goes to see its general manager, who turns out to be none other than Cynthia. Finally, they are reunited in business as well as love.