When beautiful, but shy, 24-year-old Bobbie Bertucci arrives at her new digs, an elegant brownstone in Chicago’s historic Gold Coast neighborhood, she has no idea what her new life will be like. Between balancing her job as a modeling agent and escaping a bad relationship, she’s hit rock bottom.
But things change when she moves into the same building as her close friend Meryl. Additionally, her two new twenty-something roommates, Ivy and Ella, help bring Bobbie out of her shell. Barbara, landlady and mother-hen of the house, watches out for the girls while sharing sage advice.
Bobbie, Meryl, Ivy and Ella, all variations of shy girls, brave the city of Chicago together, forming a powerful bond of friendship. Their nighttime roof deck conversations over glasses of wine instigate laughter and even some tears.
Bobbie takes a bold step to redesign her life completely to ensure she doesn’t fall into the romantic trap she fell into before. But there’s a new suitor in the picture, and she will have to decide between an old flame or a new one, taking a risk, something hard for any girl–even harder for a shy girl.