Dear Jane Letters is a light-hearted look into the life of Raina Lane, author of a local advice column titled Dear Jane. Raina has a close family who loves and entertains her at every encounter. She lives with her best friend, Vicki, who is about to get married and is anxious to see Raina paired up as well. She looks for romance between Raina and just about anyone with whom they come into contact, including a blind date and the old friend who has recently reentered Raina's life. Despite her roommate's constant vigilance, when Raina does find love, it still catches her by surprise. Note from the author:
Not the first book I ever wrote, but the first one I ever finished, I was perhaps too eager to release Dear Jane Letters. I believe the book was good, though not as good as it could have been. I released a revised and (I hope) improved version five years after the first one. I was, however, only able to update the ebook edition and having two different versions of the book never quite sat right with me. I retired the book a few years later.