At the request of her father Truman Grange, Chloe Grange, the general manager at an upscale restaurant in Portland, Oregon, heads home to Grange Family Wineries in Oregon wine country for a week respite to hear her father's news which he wants to tell her in person. This time away from work, which coincides with the Valentine's Day Wine Festival, will also allow Chloe to ponder the job offer by her boss Maggie, the new job a lateral move albeit one with more pay. Deep in her heart, Chloe already believes she's gone as far as she can go in the restaurant business without being a restaurant owner herself, but without knowing what any alternative as a career for which she has equal passion would be. She, along with the winery management team, learn that Truman's news is that, following the death of his wife - Chloe's mother - he has decided to retire. With Chloe having her own career, he has also decided to sell the winery, the most likely candidate being one of the mass producing manufacturers, New York City-based Stratosphere, sell to a company like that Truman said he would never do. Conversely, Stratosphere wants this acquisition to have one of the most respected family-owned boutique wineries under its umbrella. The Stratosphere representative who will lead the negotiations is Seth Anderson, a city boy who knows nothing about wines, but knows business, he coming back with a deal which is a prerequisite to a promotion to VP. Chloe doesn't dislike Seth per se but wouldn't trust anyone in his position where the deal would be all about business and nothing about the passion behind the wine. While butting heads with Seth, Chloe begins an increasing flirtation of sorts with whoever is renting the Grange family cottage, the person who has taken it upon himself to do minor repairs around the cottage. The renter and Chloe leave each other messages on the kitchen blackboard, the renter signing his messages "handyman" and Chloe signing her messages "in need of repair". What Chloe does not know is that "handyman" is actually Seth, who in turn does not know that "in need of repair" is Chloe. In this situation, both Chloe and Seth may come to a realization of what they consider important in life, for Chloe also including what her next career move should be, which may not be as easy to achieve as just wanting it.
