5th grade is hard; but graduating 5th grade and leaving for Middle School is harder. Damien, the "quiet" student of the class, is sorry to be leaving his favorite teacher, Mrs. Lewis, behind. However, she suggests they remain "pen pals," which means he can still write to her about all his new school and experiences. Time passes, and as a senior in college, struggling with career choices and girlfriend troubles, Damien rediscovers his old letters and starts writing again. Little does he know..... Mrs. Lewis has passed away. Her granddaughter, Lindsey, has taken over the letter-writing in an attempt to aid Damien and also prove her self-worth. Lindsey is a relationships therapist with her own complexes; her own struggling romances and a crushing case of imposter system keeps her from committing to any true relationships in her life. This strange friendship between a man too scared of the future, and a woman scared to commit to her present, will teach them both what it means to be confident in themselves, and what they seek in another partner.