Molly Dawson moved from San Francisco to New Mexico a year ago in accepting her dream job working for real estate maven Nancy Spencer. At that time a year ago, Molly thought that she and her then boyfriend, Jackson West, a vintner, were moving onto the next committed stage of their loving relationship when she discovered on his birthday, Valentine's Day, something from his recent past which she considered an unforgivable deception. She started dating stock broker Greg almost immediately upon her arrival in New Mexico, and she can only admit to herself that despite both having used the word love, what she feels for him is nowhere near the love that she felt for Jackson. Her best friend Liz, a lawyer who also works for Nancy, considers Greg to be Molly's rebound. Greg's over-attentiveness to Molly, while masquerading as love, may instead be a manifestation of Greg's rather idle life which he spends largely doing big boy stuff with his best friend, "The Rickster". Nancy receives a new client in the form of eccentric billionaire Randall Slade who wants to invest in a winery and not just any winery but up and coming Broken Heart Winery located in New Mexico which he gave an initial offer of twice the market value. Handling the case, Molly discovers upon making an appointment with Miss Tischer, the acting spokesperson for the numbered company that owns the winery, that company is now managed by Jackson. While Molly still has not forgiven Jackson, Jackson can only admit to himself that he has never stopped loving Molly and that he manufactured a reason under the guise of the purchase to spend time with her. Beyond still loving her, Jackson has many things he wants to tell her about his current life but his loyal and overenthusiastic right hand man Tomero, who likes to call himself Romeo in that being closer to his heart, takes it upon himself to help Jackson win Molly's heart all over again. Beyond Tomero's over-the-top plan, the things that Jackson has not yet told Molly, the issue of Greg, and the deal with the winery going or not going through, what happens between Molly and Jackson is affected by a blog Molly has just started following, "Wine, Women and Song"