Quote Exploration – The Great Gatsby
Saturday is the perfect time to wander through the stacks (that’s librarian-speak for “bookshelves”) and talk about books and the people who write them. Pull up a comfy chair and settle in, because today I want to do a deep dive into a quote from one of my all-time favorite books, F. Scott Fitzgerald’s The Great Gatsby.

“He smiled understandingly-much more than understandingly. It was one of those rare smiles with a quality of eternal reassurance in it, that you may come across four or five times in life. It faced–or seemed to face–the whole eternal world for an instant, and then concentrated on you with an irresistible prejudice in your favor. It 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 impression of you that, at your best, you hoped to convey.”
F. Scott Fitzgerald, The Great Gatsby
Reading this passage for the first time as a seventeen-year-old aspiring author was lifechanging. So much so that I, to this day, feel the same warmth bloom in my chest reading these words that I did those many years ago. Fitzgerald has a rare gift when it comes to characterization. He paints people beautifully, with words that go way beyond skin-deep.
At the face of it, the passage above is all about a physical feature of Jay Gatsby: his smile. But we learn so much more about the man than just that he has a winning grin — we learn about how he views people, how people view him, how he affects others, and moves through the universe. We learn, in one eloquently worded moment, that Gatsby is an eternal optimist, a man of almost irresistible charm, and that to be the object of his smile is intoxicating, perhaps even addicting. It sets the stage for our protagonist in sublime fashion.
When I read the quote above, I knew I wanted to write characters like that. I wanted to hold up one aspect of them to the light and in doing so send refractions and reflections of their innermost selves bouncing around the page and the readers’ imaginations. In fact, in my very first book, .exe: A Cadence Turing Mystery, I created a homage to this moment from The Great Gatsby with my main character, Cadence Turing, and her smile.
Is there a particular quote from The Great Gatsby that has always stood out to you? Throw it down in the comments below!