Cupid wants to retire and Ruby, one of his more hopeless assistants, wants the job. She is challenged by cupid to, before Christmas, find a match for collage professor Charlie. He has a terrible dating record and has settled for living without romance. With her normal amount of enthusiasm she goes down to earth to find Charlie the love of his life but it turns out to be harder than she thought. Charlie is very reluctant to go back to dating and on top of that she has to promise not to use any magic. It gets even more complicated when she finds Charlie really charming underneath his awkwardness.