Dear Joseph tells the story of the fabulous lifestyle of Deb a savvy world traveled fashionista and life coach who appears to have it all together except she hasn't really found her true love, though she's always searching. She loves her current man Joseph, a very successful business man with a wandering eye whom she met 3 years ago on a first class flight from Chicago to New York. Deb and her best girlfriend Janet both live on Chicago's Gold Coast Preimer neighborhood and are into the best of everything Chicago has to offer. Janet's a vegan chef, devoted wife and mother who's happily married to her college sweetheart. He's also a successful businessman and they're raising the perfect family of three well behaved kids. There's a whirlwind of drama, mystery, romance and self discovery. Deb is a woman searching for true love in Chi-town. Will she ever find it? Will she find the courage to make the tough choices she's faced with in her search?