This paper focuses on the lives, passions and destinies of Dorothy Day and Saint Augustine of Hippo have close resemblances and are strikingly parallel. They were both born into comfortably well-off families: Augustine's in Tagaste (a city in what is now Algeria), where his father was a city official; and Dorothy's in Brooklyn, New York. Both were in search of something they vigorously sought from their youth, and both had strong links with their parents: Augustine with his saintly mother, Monica, and Dorothy, with her father John Day. And both of them were endowed with the capability to achieve their pursuit: Augustine received a Christian education, although his father was baptized into Christianity only before his death; and Dorothy spontaneously found serenity and beauty in the desolate and drab streets of Chicago's south side at the time (Forest). Both possessed sharp intellect and unbreakable will. Even their timelines are parallel: Augustine was converted and baptized into Christianity when he was 33 years old and died when he was 76 years old (Knight); Dorothy was received into the Catholic Church at 30 years old and died at 75 (Forest).