100 Books Like Someday This Pain Will Be Useful to You

This is a coming-of-age novel set in 1950s San Francisco. As teenagers my best friend and I shared a mutual hyperfixation with the Cold War. It beautifully explores that era, from the Space Race to the McCarthyism that targeted both queer Americans and Chinese Americans. My best friend now lives in San Francisco, and when I last went to visit her I treated myself to going on a little walking tour of some of the places mentioned in the novel, all around Chinatown and Russian Hill.

The desire Lily feels towards her butch friend is beautiful and stirring, and the excitement she feels at exploring the underground gay scene is absolutely infectious. 

This is a peculiar and marvelous book about birth families, adopted families, and “found” families, and how each of these can be equally screwed up.

Starting in Ireland in the 1940s, the story is peppered with sharp, clever dialog and vivid, fully-human characters. I love how the narrator struggles with his own heart for decades, unable to decide what he wants, who he loves, what’s right, what’s wrong, etc.—in other words, all the stuff I haven’t figured out yet myself. 

Coincidence also plays a huge role in this book, basically making an ass of everyone, which I find oddly comforting since it reminds me that part of being human is having very little control over my own life. Painfully funny and brilliant from cover to cover. 

Another book about a misfit at a US boarding school. Frankie, our heroine, is sharp, possibly a criminal mastermind, and an ugly duckling turned pretty. At her school–Alabaster Prep–she gets in with a group of older boys and starts to undermine their secret prank society by outdoing them all, with (un)predictably disastrous consequences. This book is so much fun; adults and adolescents alike will love it. 

I love this book because gay teen Henry keeps getting abducted by aliens. He’s trying to have a normal life as a high school student in Florida, but people think he’s a flake because he keeps going missing when the aliens take him.

The aliens give him a button to push if he wants to save the world from getting destroyed. Henry’s classmates f*ck around with him so much I wanted him to find something to give him hope not to destroy the world. His new boyfriend seems to be helping, but during a visit, Henry is taken by aliens and goes missing for a while, messing up his new romance.

It’s hard enough to be a gay teen, but to be a gay teen who is abducted by aliens on a weekly basis is something that I love about this book.

The Lost Episodes of Revie Bryson is another book that will make you laugh and cry. What I love most about it is its wondering tone which makes me feel like I’m trying to figure out twelve-year-old Revie Bryson’s world right along with him. Why did his mother make up lost episodes of the Bible that made him feel like he just might be the second coming, why did she leave him and his dad in Paris, Indiana to pursue her dreams of Hollywood—and where is God, anyway? Aren’t you supposed to be able to count on Him to make things right? 

Fifteen-year-old Jam’s boyfriend has died, and she’s been sent to the Wooden Barn, a therapeutic boarding school. Assigned to a selective class called Special Topics in English, Jam and the other struggling students discover that a journal-writing assignment transports them to a place where past trauma seems to be undone and the dead are returned to the ones they love. But as Jam spends more and more time in a static version of her boyfriend’s afterlife, she must figure out if she should hold on to what she once had or reach for something else. Belzhar is twisty tale of magical realism that I will never stop thinking about.

“Everyone has something to say. But not everyone can bear to say it. Your job is to find a way.” 

Also super funny while pointing out the absurdity of academia. Written from the perspective of the chair of the English Department, Henry Deveraux grapples with being the underachieving son of the man who is the father of American Literary Theory.

An excerpt of Straight Man titled Dog appeared in the New Yorker many years ago, and it’s possibly the best excerpt I’ve ever read. It taught me so much about writing while keeping me riveted to every sentence, just like the overall book did.

I love this novel. It’s about a young man mourning the death of his wife and trying to deal with crippling grief while also repairing his relationship with his sixteen-year-old stepson. With such a premise you wouldn’t think the book would be funny, but it’s both hysterical and emotionally touching. 

Trooper has a gift for making extremely dysfunctional characters lovable, putting them in ludicrous situations and turning them loose on each other. This book really resonated with me because of the damaged-yet-enduring family dynamic after the death of a loved one, which is similar to my own experience following the death of my father. 

The evolving relationship between the main character and his stepson is also great, and Tropper nails the adolescent angst I remember so well from my own childhood.

My friend and fellow novelist, Allison Pittman, recommended this one to me.

It’s a story told in letters written between a goofball kid named Joey and a New York Giants player named Charlie. I laughed and cried my way through this winner of a novel, rooting for both Joey and Charlie the entire time. It’s a story about the love of baseball, yes.

But it’s also a book about ambition and friendship, heartache and dreams, disappointments and hope. And with every page I read, I fell more and more in love with baseball. It’s one of the finest novels I’ve read.

Although we have very different voices and approaches to a similar question, ‘How do society and our patriarchal conditioning warp our girlhood?’, we write about it in very different voices and from a different perspective.

I read her to hear what another girl/woman who felt the same pressure was able to express and move on from. Interestingly, I grew up and seemed at home as an escort, and in another of her memoirs, Ms. Febos became, for a time, a dominatrix. I found that fascinating as well.