Twenty-year-old Ruby Gale has a secret. After all, unmarried women in 1895 can't be too careful. Especially when it comes to matters of business—not to mention the human heart. After the untimely deaths of their parents at a young age, Ruby is grateful for her older brother Simon, a prominent attorney in the small town of Divine, CO, for caring for her during her formative years. However, now that she's reached 20 years of age and is looking towards marriage, Ruby wishes he could see her as the woman she's become instead of the child she once was. Eager to take on the responsibilities of adulthood, Ruby agrees to invest in a greeting card business with several of the other ladies she knows in town. Valentine’ Day is just around the corner, so the timing couldn’t be better. However, because some of the married ladies suspect their husbands may not welcome the idea of their wives working, it’s decided that the card-marking activity will take place under the guise of tea parties to avoid suspicion. The talk amongst the unwed members of the group—including Ruby—soon turns to prospective beaus and secret crushes and suddenly unsigned valentines begin showing up in the hands of the most eligible bachelors all over town. Rumors and speculations abound, and everyone thinks they know who’s sweet on who. Suddenly, Ruby not only has to sort out the identities of the secret admirers, but also answer the question of which man to give her own heart—and why.