Unedited thoughts on "This Side of Paradise" by F. Scott Fitzgerald

Published on Mar 11, 2026

Ever since reading The Great Gatsby (1925), I've been interested in the work and life of F. Scott Fitzgerald. Even though until reading This Side of Paradise (1920), Gatsby was the only book of his I had read, Fitzgerald always had a unique aura that kept him in the back of my head at all times.

Though commonly associated with the 1920s, This Side of Paradise actually takes place during the early 20th century, shortly before and after the first World War. However, because so many aspects of the the 1910s overlap with the 1920s, the book still evokes that classic Fitzgeraldian feeling of youth and hopelessness that he's so well known for.

As this book is a semi-autobiographical tale of Fitzgerald's own adolescence, there is a stronger focus than Gatsby on coming of age and loss of innocence. I have always loved this theme in all forms of art, from the music of Pet Sounds to the cinema of Almost Famous, and this book does a good job of bringing to mind images from simpler times.

I. College life

After a short beginning describing the upbringing of the main character and the, Amory, he is thrust into a prep school far away from his parents. This is where he first gets his thirst for notoriety and belonging which persists throughout the entire book.

Without a doubt this was the least memorable part of the book and, for me, a sort of slog to go through. We are gradually introduced to the unique structure of the book and Amory's uniquely conceited personality, but the stakes and low and the plot barely seems to slug on. Mosts books I've read seem to use a lot of their strength in the beginning and then save the rest for the climax and the end, but this book kept things low at the start and kept ramping up, eventually peaking at the climax.

Where the book really began to grip me was around the point where Amory began his tenure at Princeton. Perhaps because I went to an old university and could relate to many of the things and scenes Amory finds himself in, I adored the college portion of the book; scenes of sitting on the university green just laying in the grass, chatting with your roommates on a window sill, going for long walks in the dark of night, going out with other similarly minded young people, and so on.

My own experiences with these scenes all came back to me like hazy clouds of nostalgia, bursting and moving along with the same qualities that made them so memorable in the first place.

For me, this section peaked when Amory witnesses his friend die in a automobile accident. Up until then, it was like a stream of anxiety and partying, a crazy ride that forced me to speed through the pages, eventually coming to a literal and figurative halt that ends the first part of the book.

II. The war

Having mentioned the structure of the book previously, I'd like to discuss it in a little more detail.

On the broadest level, the novel is split into two "books," which correspond respectively to Amory's life before and after World War I. Then, each book is split into half a dozen or so chapters and finally each chapter is split into a multitude of named vignettes. These vignettes make the book feel like a large collection of snapshots; some are quite short, while others are long, and many diverge from the few plot threads that emerge.

The precise center of the book, where Amory serves in World War I, was surprisingly short. Amory's actual experience in the war is mostly ignored (as its implied it was mostly boring) and instead the focus lies on how the war changed his perception of meaning. A core part of the book is in fact Amory's search for meaning, but the scars the war left on him in this regard are subtle.

III. Rosalind and Amory's fall

Barring small but important love interests Amory has during the first half of the book and Elenor later on, Rosalind was the most consequential love interest Amory falls for in the entire book. Besides Amory, Rosalind is perhaps the most important character of the whole book.

Rosalind is the younger sister of Alec, a longtime friend of Amory's from his Princeton days. Like Amory she is somewhat conceited, highly intelligent, and beautiful. Importantly, her family has a high social status, unlike Amory. Almost immediately, they fall for each other.

Perhaps attracted by their wits and their good looks, the two of them form a very intense relationship. The intensity makes the reader feel, by the end of it, as if they have been together for years. But their relationship was less than a year long.

Rarely throughout the book is Amory openly happy; with Rosalind, he is brimming with joy. To him, she is everything; Fitzgerald's account of their love really moved me and showed that he too has felt much of what Amory felt. Unfortunately, in spite of their love, Rosalind breaks off the relationship because of Amory's lack of money and social status.

Rosalind is a girl who requires nice amenities and social stability; tenets she prioritizes even over true love. She believed that she would begin to resent Amory for his low social standing and it would be better to break it off while they were in love than to allow it to fade. This, of course, destroyed Amory.

He spirals in alcoholism and debauchery, eventually getting into a fight which leaves him battered and bruised. Financially, as the book goes on, he also degrades; by the end of the book, he has almost no money to his name.

Amory struggles because, though he understands himself extremely well, he fails to understand that others don't live by his ideals, and just because he thinks he is beautiful and deserving of fame, he won't necessarily get it. And so he loses his optimism and spirals.

IV. Eleanor and the night-raid

While on a trip in rural Maryland, Amory meets Eleanor. She is just like him: egotistical, literary, and highly intelligent. For Amory (also highly literary and thus prone to adeventure-seeking delusion), this seems to him an ideal woman to have an affair with. Ultimately, their relationship is doomed (both due to the fact that Amory will eventually go back home and because she is what he thinks he wants, rather than what he actually wants).

In a highly dramatic moment, in order to prove her disregard for society, she drives herself and her horse she is riding off a cliff, injuring herself and killing the horse. This moment, which is the pinnacle of what Amory sees as the idea of Eleanor (dramatic, pagan, brave) is actually where he sees the discomfort of his vision. Her lack of stability and self-destructiveness act almost as a mirror for himself, causing him to lose any attraction for her.

It is interesting because they are almost identical in many ways. Eleanor is simply more herself than Amory is; they share the same ideals and visions for themselves, but Eleanor is more willing to live it. As a result, his sense of romanticism is lost, and he loses hope in love at all.

Later on, while he is drifting along in borderline poverty, he goes with Alec and a prostitute to a hotel to party. Somehow, the hotel caught on to Alec's intentions and, due to the laws at the time, the group has detectives knocking on their door. With Eleanor, he merely pretended to be someone. Now, he could act, and live what he merely used to pretend to be.

He takes the fall for the prostitute as both an act of loyalty to his friend who he sees as having better prospects than himself and a literary act of heroism; he wants to be somebody. In reality, this act ends of casting him as a degenerate in society and he is left alone; there is no drama, no heroism, just loneliness and societal disillusionment.

V. Final, random thoughts

Monsignor Darcy

Early on in the book, we are introduced to the character of Monsignor Darcy. He is a cousin of Amory's mother, Beatrice, and someone Amory seems to look up to throughout the book.

I see Darcy as a warped mirror of Amory; it is the Amory that never lost his idealism, the Amory that, in spite of the pain of reality, chose instead to devote himself to his talents. Just like Amory, Darcy is remarkably intelligent. The difference between the two is that Amory sinks when faced with the meaninglessness of society and Darcy commits himself to his faith.

Beatrice

The mother of Amory, Beatrice, is an interesting character who bestows in Amory his conceited and cultured nature. In a sort of Freudian way, she also gives Amory his desire for strong, intelligent women that drives his choice of love interests throughout the book.

Clara

Perhaps the most unique love interest Amory has throughout the entire book, Clara is a distant relative and recent widow who Amory falls for. Unlike Rosalind or Eleanor, Amory truly respects her. This is because, unlike the other girls, she is willing to call out Amory's narcism and actually lives according to her ideals.

That she is good and that their relationship is purely platonic and that she rejects Amory on the grounds that he doesn't love her but the idea of her all make Amory fall for her even more. By the end of their short friendship, Amory respects her as one would a saint. She represents the "holy," or perhaps the unfettered "good" of a person.

Burne

Burne is the brother of Kerry, a great friend of Amory's who dies in the war. Burne rejects social convention and lives according to his values; a style of living which Amory seems to greatly admire and gets inspired by. He is a pacifist which ultimately ostracizes him from the school, but in this isolation he gains a sense of purpose. He makes Amory want to be somebody.