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7 Books to Read and Songs to Listen to During Sadboi Hours

According to Urban Dictionary, sadboi is defined as a young male who spends most of his time in his feels and often questions what life has in store from them. In other words, it’s…most of my guy friends. Existential crises every day. Wondering “what-if” from just one interaction with someone they see even a slight romantic future with. Constantly listening to songs from Drake, Lauv, keshi, ILLENIUM, The Weeknd, and the like.

The more I talk about it, the more I realize that I might be a sadgirl—but I’m not here for self-realization, I’m here to talk about my favorite squishy sadbois in YA lit in the method I know best: by comparing them to songs. Sadboi hours starts now. Ends never.


Evan from Dear Evan Hansen: The Novel by Val Emmich, Steven Levenson, Benj Pasek, and Justin Paul

That’s not a worthy explanation
I know there is none
Nothing can make sense of all these things I’ve done

How can I not use a DEH song for our resident sadboi Evan Hansen? When a letter that was never meant to be seen by anyone draws him into a family’s grief over the loss of their son, he’s given the chance of a lifetime: to belong. Suddenly he’s not invisible anymore—not to the girl of his dreams, not to the school, not to the world. But he knows that what he’s doing can’t be right, so when the truth begins to unravel, he comes face to face with his greatest obstacle: himself. And what’s the biggest obstacle for any sadboi? Say it with me, now: THEMSELVES.


Sam from Emergency Contact by Mary H. K. Choi

Sometimes it feels like I don’t belong here
Roots can’t take hold ’cause I didn’t fit
Can’t see the way out through all my tears
I know they always say to hold on for better days

Ugh, Sam, our precious baby Sam. He works at a café and sleeps there too. His ex-girlfriend comes and goes from his life as she pleases. He has $17 in his checking account. His aspiration for becoming a famous movie director is what keeps him holding on. Then he meets Penny in an unbearably awkward encounter and they find themselves sharing their deepest anxieties and ambitions with each other. I also have to say that Pablo from Permanent Record is also a super sadboi. Mary H. K. Choi is just so good at writing them.


Frank from Frankly in Love by David Yoon

dream about the days
love me
tell me that you’ll stay

Frank Li’s parents have one rule when it comes to romance—“Date Korean”—which means that the smart, the beautiful, and the white Brit Means is out of the question. Family friend Joy Song is also in a similar situation, so they come up with the perfect plan: FAKE DATING. But then he starts questioning whether he understands love at all and wonders who The One for him really is. It’s the perfect mix of teenage angst and anxiety caused by first love, college applications, and identity. God, it’s like reading about my own teenage years.


Cardan from The Folk of the Air series by Holly Black

How I still love you
I still love you
But sometimes you have to go
Trade your heart for bones
To know you need to come back home, come back home

Cardan “Softboi” Greenbriar is in the house…and he’s waiting for Jude to come back. Please refrain from the urge to @ me about this, because you have to admit that by the end of The Cruel Prince, he’s 100% the brooding sadboi we all saw coming after he scrawled Jude 198 times on a piece of paper. To be fair, though, if I were him and my love interest was giving me some tough love that makes me wonder either it’s unrequited or just CRUEL, I would be hella sadboi, too.


Miles from Looking for Alaska by John Green

I got my reasons but I get caught in my feelings
And I don’t wanna say bye, don’t wanna say bye bye

Okay, Miles is in his feelings for a really good reason, but he was a total sadboi before The Thing even happens. I mean, he changes high schools to seek his own “Great Perhaps.” AND THEN, when he meets the beautiful and unpreditable Alaska, they make a deal to figure out what the labyrinth from Simón’ Bolívar’s last words—“Damn it. How will I ever get out of this labyrinth!”—is. When an accident happens, Miles blames himself for it and is obsessed with figuring out whether it was truly an accident.


Watt from The Thousandth Floor series by Katharine McGee

Give me reasons we should be complete
You should be with him, I can’t compete
You looked at me like I was someone else, oh well

Maybe it’s because they both have “Watt” in their names, but Watt from The Thousandth Floor series reminds me of Wade Watts from Ready Player One, who most definitely is a major sadboi. Watt is head-over-heels with Avery, who is levels above him (literally and figuratively), but Avery is in love with someone else. He digs and digs until he finds out who it is—regretfully—and falls down a rabbit hole of wondering why and what-if.


James from The Hearts We Sold by Emily Lloyd-Jones

And it’s a long way forward, so trust in me
I’ll give them shelter like you’ve done for me
And I know, I’m not alone, you’ll be watching over us
Until you’re gone

JAMES LANCER, THE ABSOLUTE LOVEBUG. If you’ve read the book, then you know that Shelter is the perfect song for him. Why? Because throughout the duration of him and Dee’s friendship, he’s constantly trying to protect her and make her see the bright side of things. While he’s one of the cheerier ones of the sadbois on this list, the struggling artist in him (he legit traded his heart to the Daemon in PARIS of all places) shows through. When Dee is threatened to never get her heart back, he does the UNTHINKABLE and launches himself and the reader into a black hole of feelings.