As Christmas approaches, Paula, a St. Louis antique appraiser, reluctantly accepts a marriage proposal from her boyfriend, Daniel, a career-focused attorney. When her Aunt Jane 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 a charming inn owner.

Katherine, a high-powered executive who believes men are intimidated by her career, is persuaded by her friend to create an internet dating profile claiming she is an executive assistant.