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Founded in 1903, Angelini's, which makes custom designed wedding shoes the old fashioned way i.e. by hand, is a family business located in the same Greenwich Village building since day one. It is currently owned by second generation, long-widowed Teodora Angelini, her father the company founder. Her maternal granddaughter Valentine Roncalli is the only one in the subsequent generations who has ever had an interest in the business, she now the chief designer, the company which she sees as her life and future. As is history, Valentine and Teodora live above the ground floor shop, everything about it which Valentine loves, especially the rooftop garden, despite the building having none of the modern comforts. Among her and her three siblings, Valentine is the only single one in her focus on work, and in not being the "smart" or "pretty" one but rather the "funny" one. The business is stuck in the twentieth century in almost every way, and as such is failing financially despite Valentine and Teodora constantly being busy. As such, Alfred Roncalli, Valentine's brother, wants Teodora to sell the property, which would probably be worth millions, and shut down the business, something that both Teodora and Valentine are resisting despite the financial problems. Teodora and Valentine may be able to get the business out of their financial hole when one of Valentine's shoes are noticed by Rhedd Lewis, the powerful head buyer for a chain of upscale boutiques, she who asks Valentine to submit a pair of shoes for specific wedding gown in a competition among the major shoe companies, the winning pair to be featured in the boutique window. Concurrently, Valentine herself, against what she would consider the odds in not being her own idea of the perfect woman, catches the eye of Roman Falcone, an up and coming executive chef at an upscale neighborhood Italian restaurant. Without the proposal itself, Roman quickly lets Valentine know that he sees a long term future for them. Along with the pressures of work on both sides especially with the shoe competition, Valentine isn't sure she can trust Roman when she learns that his publicist, Sienna Rutledge, was once his year long girlfriend. While she has those trust issues, Valentine, in accompanying Teodora on what is always her solo trip to Italy to meet with suppliers and to get some inspiration, Valentine, invited along to get some of that inspiration for the competition, may not only find the reason for Teodora always taking these trips by herself, but also may see an alternate future for herself and her grandmother.