As Christmas approaches, Paula (Sustad), a St. Louis antique appraiser, reluctantly accepts a marriage proposal from her boyfriend, Daniel (Giles Panton, Chesapeake Shores), a career-focused attorney. When her Aunt Jane (Gifford) senses she has mixed emotions over the engagement, she invites Paula to her Nantucket home. Upon her arrival, Paula plans a trip to the nearby island of Martha's Vineyard where she meets Gery (Campbell), a charming inn owner. When bad weather prevents her from departing, Paula winds up staying at Gery's inn and enjoying local holiday festivities alongside him. They begin to have feelings for each other but when the weather clears up, they part ways and Paula returns to Nantucket. Sensing she's fallen for Gery, Aunt Jane shares with Paula her belief that their meeting was God's way of "winking" at her to help determine which direction her life should take. When Daniel surprises her by spontaneously arriving in Nantucket, Paula decides to move forward with their marriage plans. But back in St. Louis, Daniel soon returns to his all-business ways and a fed-up Paula finally realizes they're not compatible. When Jane invites her back to Nantucket for Christmas, Paula accepts, unaware that Jane has devised a plan to bring her and Gery together. From author, SQuire Rushnell of the God Winks book series.