Artist Olivia Lafferty has lived in New York City for two years with her professional life not yet having taken off, she and her actor best friend Tess, on whose sofa she has been sleeping for those two years, working as servers for a catering company to make ends meet. When Tess gets her big break which means an immediate move to Chicago, Olivia is forced to move out of their shared apartment by Valentine's Day two weeks away, made even more difficult as she, this time of year usually heading home to Valentine NE which the town does big for its namesake day, was unable to secure a flight home. In running into her wealthy and successful distant Los Angeles-based cousin George Kessler at a high end event catered by the company for which she and Olivia work, Tess, upon learning that George is driving back to Los Angeles in a family owned classic car, suggests he give both of them a ride, Tess to Chicago and Olivia to Valentine, which he is more than happy to do. Upon arriving in Valentine, George is faced with a time issue in making it back to Los Angeles for a meeting on Valentine's Day when the Board of the family company, Kessler + Kessler Asset Management, will vote him in as next CEO taking over from his father, the now malfunctioning car wanted by Kessler Sr. for the celebratory event following. In their time together in Valentine, Olivia and George have to get over some points of contention, which masks the mutual attraction that exists between the two. As George works to get his car fixed and as Olivia helps her sister Vanessa with the annual Valentine's Day Parade which she has taken over from a bitter Miss Hackey who was pushed out of the role after thirty years, they may help the other find their path in life, for George specifically to find his passion as opposed to the destiny set by his father, with that help borne out of Valentine's motto of love.
—Huggo