Existentialism is a perspective on life where the existence of individuals is meaningless, and it is the individual’s responsibility to imbed purpose and meaning into his or her own life. Authenticity is one of the important characteristics associated with existentialism because of the battle between inauthentic life and authentic life where an individual believes he or she is implementing significance to his or her own life, but is instead blurred from the true meaning of their own existence. Furthermore, authenticity corresponds with boundary situations, which are unavoidable and make an individual muse about life and often pushes the individual to realize that they are living an inauthentic life that is blinded by illusions. Correspondingly, the idea of authenticity is demonstrated through the three distinct characters in the short story “A Clean, Well-Lighted Place”. In Ernest Hemingway’s “A Clean, Well-Lighted Place”, the author suggests that as age progresses and one gets older, it becomes apparent that one’s existence is meaningless because of the individual’s transition from an inauthentic life, to an authentic life. Throughout the story the young waiter is seen as a superficial naive character that has a blurred vision of life because of his young age and illusions, which are the reason for his inauthentic way of life. The young waiter, with his profound confidence and naivety believes he has life all figured out: “I have confidence. I am all confidence”.