Riot Headline Book Riot’s 2025 Read Harder Challenge
Humor

The Worst Books to Bring on a First Date

This content contains affiliate links. When you buy through these links, we may earn an affiliate commission.

Vivienne Woodward

Contributor

Vivienne Woodward lives in Philly and works as the events coordinator for an indie bookstore. She can often be found drinking too much coffee in the sunny spot on her couch and over-identifying with fictional characters. She enjoys collecting hobbies, dancing to radio pop, and rearranging the book stacks on her side tables.

You go on a first date; you order Spaghetti Bolognese and your date orders a Margherita Flatbread. You agree to share a tiramisu. You split the check after some flirtatious arguing and then your date walks you to your subway stop. You reach into your bag for your wallet and your train read flops out. Your date recoils; the kiss they were considering now turned to dust and disgust. You try to shove the book back into your bag, but it’s too late. “It’s, um, for research,” you say, blushing. “Yeah, no, of course,” they say, “but on an entirely unrelated note, I am going out of town for the next six months. Good night!” 

Has this ever happened to you? 

Has your taste in books been the thing holding you back from a thriving, energetic dating life? First thing: you should invest in a bag with larger interior pockets — your book should not be falling out of your bag so often! Second: you will want to reevaluate the books you are bringing with you on first dates. Even if your book is securely hidden, you never know if your date will peek into your bag while you’re in the bathroom. You should hide everything about your taste in literature if your taste in literature is leading to zero second dates. To that end, here is a list of books you should never, under any circumstances, bring with you on a first date. 

cover of Parable of the Sower

Parable of the Sower by Octavia Butler

Do you want your date to know, right off the bat, that you have no hope for the future of humanity? Yes, Butler is terrifyingly prescient. Yes, it’s okay to talk about things like your favorite food and how many tacos you want to order before you tackle the bleak future of humanity. 

The Witches by Roald Dahl

The Witches by Roald Dahl

Are you a child? Is it Halloween? If not, then you’re probably a witch and you should probably be hiding it better on first dates.

1,000 Books to Read Before You Die by James Mustich

1,000 Books to Read Before You Die by James Mustich

Honestly, how is anyone supposed to imagine building a life with you when you’re clearly going to be reading pretty much every minute between now and the day you die? Also, carrying this book around will probably give you back problems — not the most desirable quality in a mate. 

cover of Eileen by Ottessa Moshfegh

Eileen by Ottessa Moshfegh

Ottessa Moshfegh is a master of writing terrible people in terrible circumstances. Maybe give it a few dates before you reveal to your date how much you enjoy reading about the dark and twisted depths of the human soul.

cover of The Handmaid’s Tale by Margaret Atwood

The Handmaid’s Tale by Margaret Atwood

If you’re reading The Handmaid’s Tale now, it’s either because you’re studying for survival tips or you are intrigued by its political viewpoints. Either way, it’s going to be a major red flag to your date. 

cover of Lolita by Vladimir Nabokov

Lolita by Vladimir Nabokov

This one kind of speaks for itself, right?

cover of My Struggle by Karl Ove Knausgård

My Struggle by Karl Ove Knausgård

Not to diminish anyone’s struggles, but showing up with 600 pages of them to a first date feels like a little bit much, no? 

cover of The Memory Police by Yōko Ogawa

The Memory Police by Yōko Ogawa

Whether you’re obsessively holding on to memories like the protagonist in Ogawa’s book or trying to erase them like the titular police, neither is a good look for the start of a relationship. One suggests you might be a bit clingy and one is straight up gaslighting.


We could go on, but essentially, what we’re trying to tell you is this: your taste in books should reflect zero fear, zero ambition, and zero personality on first dates. Are you beginning to understand? May we suggest a copy of The Great Gatsby