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.

Real estate mogul Kate has a stuffy proper boyfriend but no social life. Jack, a pediatric R.N., can't compete with doctors in the dating scene. Kate's assistant Debbie builds Kate an online dating profile, using her own name. Jack starts his own profile but his buddy changes his occupation to physician, not realizing that there is a genuine Dr. Jack Cooper. The couple is matched, and start getting to know each other...but just who is it they are getting to know?