Olivia Jones accompanied by her nine-year old troubled daughter Tess agrees to write the memoirs of Natalie Seebring, owner of the Asquoniet Vineyard and Winery in Rhode Island. Natalie stuns her adult children, Susanne and Greg when she announces her intention to marry Carl Burke, the long-term manager of the winery although their beloved father has been dead only six months.
Iit is a struggle for her to talk about her feelings, Natalie hires Olivia to help her tell the truth to her children in order to gain their blessing for her wedding. Olivia is unaware that she is entering a major family feud. However, she quickly comes to love her employer, who makes her and her daughter feel like part of an extended family. Carl's son Simon makes Olivia want to believe in fairy tales, but she fears that he will desert her like everyone else in her life has done. Olivia, the Seebrings, and the Burkes have many personal obstacles to overcome if they are to learn what true loving means.