One of the best passages throughout the Great Gatsby in my opinion is in chapter three, when Nick describes Gatsby's smile for a full paragraph. Early on, Fitzgerald establishes Gatsby as an extremely persuasive and charismatic character, writing that Gatsby had "one of those rare smiles with a quality of eternal reassurance in it". This creates an expectation for Gatsby's persona as someone who is trustworthy and noble - a persona that is quickly broken down as Gatsby is exposed as a bootlegger. Furthermore, Fitzgerald utilizes numerous dashes when describing Gatsby's smile, writing "[Gatsby's smile] faced - or seemed to face - the whole eternal world for an instant". The dashes set off reality - "faced" -  with illusion - "seemed to face". Again, Fitzgerald hints at the uncertainty of Gatsby's past and the numerous lies he creates to reach a relatively mundane goal.

Gatsby's smile also reveals that he doesn't see an entire situation clearly, only noticing what he wants to see. Fitzgerald writes: "[The smile] understood you just as far as you wanted to be understood, believed in you as you would like to believe in yourself, and assured you that it had precisely the imperssion of you that, at your best, you hoped to convey." Gatsby is shown as such a strong optimist to the extent that it begins to hurt him. His optimism forces him to constantly attempt to relive the past. He believes that simply because he loved Daisy five years ago, she would simply return the love when he returns. Furthermore his optimism causes him to fail to register that Daisy is married and has a child, driving him to pursue a dream that is already dead.