After a whirlwind life as a top-tier real estate agent in New York City, Fiona Rangely (played by Lacey Chabert) finds herself heartbroken when her boyfriend breaks up with her. Seeking solace and a chance to reflect, she retreats to her family’s charming inn in Vermont. Her plans take an unexpected turn when her former boyfriend, Nate, arrives at the inn with a new girlfriend. Determined to win him back, Fiona concocts a scheme to make Nate jealous by pretending that the inn’s charming and easygoing head chef, Derek (portrayed by Carlo Marks), is her new partner. As Fiona and Derek play the part of a couple, both are caught off guard by the genuine feelings that begin to surface. Fiona soon discovers that life’s most rewarding experiences often require patience and come when least expected.