Brynne Ropert and Portland Dolish have been best friends since being paired as roommates in college. Seven years later they are now twenty-five, married, and living in Maine-- but the two women couldn't be more different. Brynne finds fulfillment in her life as a wife, mother and owner of a small café and bookshop, but is struggling to expand her family. Portland is still coping with her mother's death during her childhood, and her marriage is unraveling before her eyes. Portland envies her friend's seemingly stable and easy life while Brynne doesn't understand the growing distance between them and cannot begin to guess what secret Portland is hiding about her husband and crumbling marriage. While one woman feels shut out, the other enters into a web of lies to protect herself. A Questionable Friendship explores what really makes someone a true friend, a support system, a sister. How much trust goes into a friendship and when is being a friend not enough? Brynne and Portland's story will attempt to answer those questions, and show that happily ever after isn't in the cards for everyone.