We have updated our Privacy Policy Please take a moment to review it. By continuing to use this site, you agree to the terms of our updated Privacy Policy.

YA Sadbois Ranked from Emo to Woobie

This list is brought to you by Taylor Swift’s folklore and evermore, otherwise known as “summer depression” and “winter depression.” We all love a sadboi. From the “woobie,” who you just can’t help but feel bad for, to the true “tragic hero.” We love them all, despite the fact that many of them have a tendency to take out their angst on those around them. Hopefully (and this is the best part of sadbois imho), they eventually learn to process all of that sadness and transcend their emo origins. So, here’s a ranking of some of our favorite YA sadbois. Please send them all good vibes, they truly need them. (Pro tip: Listen to “happiness” while reading this list for maximum sadboi feels.)

1. Cardan Greenbriar from Folk of the Air

By Holly Black




2. Edward Cullen from The Twilight Saga

By Stephenie Meyer


This dude up and fled the country to get away from his own feelings. There was also that whole dark period in the early vamp days.


3. Akivafrom Daughter of Smoke & Bone

By Laini Taylor


There are some windows that have personally felt the strength of Akiva’s despair. And that’s all I’ll say about that.


4. Evan Hansen from Dear Evan Hansen: The Novel

By Val Emmich, Steven Levenson, Benj Pasek, Justin Paul


Many sadbois have angst to spare. Evan Hansen has full-on anguish, and he readily inflicts it on himself. (Someone please hug Evan.)


5. Jameson Hawthorne from The Inheritance Games

By Jennifer Lynn Barnes


Torturing yourself over something you 100% did not cause? Distancing yourself from meaningful connection to avoid pain? Yeah, that’s a certified sadboi.


6. Prince Castian from Incendiary

By Zoraida Córdova


Oh, I’m sorry, did you come here for a tragic backstory??? *laughs maniacally*


7. Adam “Kurl” Kurlansky from We Contain Multitudes

By Sarah Henstra


Honestly, both We Contain Multitudes boys could have made this list. Kurl takes the edge though.


8. Thomas Cresswell from Stalking Jack the Ripper

By Kerri Maniscalco


Literally deduces information by completely detaching from his feelings. There’s also the bit about single-handedly pursuing a cure for a certain illness for a certain family member.


9. Aiden from Fence: Striking Distance

By Sarah Rees Brennan


Aiden may pretend to have everything he wants, but we all know he doesn’t have the one person he really wants (and Aiden knows it, too). Use your words like a grownup, Aiden!


10. James Lancer from The Hearts We Sold

By Emily Lloyd Jones


Actual “heartless” tortured artiste.