Aaron is a thirty six year old man with two kids and a high end job. However, he recently divorced his wife Katie. Much to his surprise, she let him have their children, the house, and practically everything they ever owned. She told him she was going to live with her sister. But when he opens the blank envelope sitting on the doormat, with the words titled "Dearest Aaron..." his life changes forever. "Dear Katie..." is a twisted story of regret, depression, redundancy, debt and loss...and endless endless letters that drift up into the clouds on a wind of pure sorrow.