The High School Books You Should Re-Read as an Adult

Let's be honest: you probably didn't appreciate these the first time around.

Did 16-year-old you really understand the full complexity of everything you were assigned in high school English class? Exactly. For most of us, the formative years were filled with classic literature that we read skimmed SparkNotes for, wrote a paper on, and then promptly forgot. Somehow the only Hemingway knowledge that seemed worth retaining was his go-to Daiquiri recipe (1.5 oz rum, .75 oz lime juice, and .25 oz each grapefruit juice and maraschino liqueur).

The classics, though, are classics for a reason – missing out on their wealth of knowledge just because we crossed them off our reading lists when we were too young to fully appreciate them would be a damn shame. So in that spirit, here are six classics from your high school reading list that are well worth revisiting as an adult. 

The Bell Jar

by Sylvia Plath

What it’s about: While on a big city internship in college Esther Greenwood struggles between choosing a safe, conventional domestic life or the dangerously exciting and unconventional pursuit of ambition. All while trying to lose her virginity.

The theme you missed in high school: Neither path is without its pitfalls.

Why it’s important to your adult life: Aside from the virginity thing, Greenwood’s dilemma was probably kinda unrelatable for high school you. But as an adult, it’s actually a little too real. Life is full of potential paths from the conventional to the risky, and all the fat purple figs in between. The point is that the act of choosing one is, sadly, going to close off others – so decide carefully.

The Catcher in the Rye

by JD Salinger

What it's about: Salinger’s famous novel is narrated by 16-year-old Holden Caufield who recounts a few wild days he spends in New York before winding up in treatment in a mental institution. 

The theme you missed in high school:  Phoniness isn’t so simple. 

Why it's important for your adult life:  Caufield is the king of angst. And 15-year-old you loved him and his caustic accusations about the “phoniness” of the adult world. But re-reading this classic as a 20-, 30- or 40-something delivers a massive dose of perspective. Suddenly that isolated no-one-understands-me attitude you identified with looks simply immature. 

The Great Gatsby

by F. Scott Fitzgerald

What it’s about:  Midwesterner Nick Caraway moves into a New York neighborhood for the nouveau riche where his neighbor is the enigmatic and ridiculously wealthy Jay Gatsby: thrower of extravagant parties, owner of a mysterious past, and estranged beau of Nick’s beautiful cousin Daisy Buchanan. 

The theme you missed in high school:  Being able to look yourself in the eye is worth more than fancy cars or a swank apartment in the city. 

Why it's important to your adult life: In high school, Jay Gatsby was the big brother you never had. The ultimate party boy seemed like he had everything figured out. Meeting Gatsby as an adult paints a sharply different picture of frivolity and misguided ambitions that will leave you marveling at the epic waste of it all. Suddenly Nick Caraway seems way more like your kind of guy. 

This Side of Paradise

by F. Scott Fitzgerald

What it’s about: Fitzgerald’s debut novel chronicles the life of Amory Blaine, a wealthy kid who skates through most of his formative years before desperately setting out in pursuit of self-knowledge. 

The theme you missed in high school:  Figuring out your purpose is the whole point. 

Why it’s important to your adult life: Similar to Jay Gatsby, Fitzgerald’s Amory Blaine has that whole too-cool-to-care thing going we all wish we could have mastered in high school. But Blaine is actually way easier to identify with as an adult – the guy has no idea what he’s doing with his life and spends the majority of the book trying to figure it out. We’ve all been there.

The Old Man And the Sea

by Ernest Hemingway

What it’s about: After an 84-day dry spell, a weathered old fisherman struggles with the catch of a lifetime. 

The theme you missed in high school:  Sometimes perseverance is the whole point.

Why it’s important to your adult life: In your teens, The Old Man and the Sea is hopelessly mundane. Why doesn’t this guy just give up already? As an adult, though, it all makes sense. Trying and failing (and trying and failing again) is all part of a worthwhile life. 


by Joseph Heller

What it’s about: Catch-22 follows a group of soldiers stationed in Italy during the second half of World War II as they navigate a war defined by bureaucracy and a bevy of ridiculous and absurd battle situations. 

The theme you missed in high school:  The harsh reality of war.

Why it’s important to your adult life: As an adolescent, Catch-22 is an odd, kind of funny read. But Heller’s style of satire is such that you might have missed the real point: there’s nothing funny about the brutality of war. As an adult, you’ve got a fresh pair of wizened (if not jaded entirely) eyes to read with – and suddenly, the soldiers’ stories seem a lot more real. 

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