Hot Literati: a Book Club for Hot, Cool, Well-Read People in NYC and Beyond

Hot Literati is more than a book club — it’s a community built on curiosity, connection, and a bit of flirtation with the world. We caught up with founder Hailey to talk about train rides, TikTok, critical thinking, and the philosophy behind “flirty fall.”

Hailey took the call from the streets of London where, in true artist fashion, she followed a hunch to finish her latest book.

What brought you to London?

I’m working on a book about America, food, media, and culture — and how polarized it all is. I wanted to get perspectives outside of America about America.

I work best when I travel. Sometimes when I have a hunch, I’ll follow it — which is a little reckless, but it keeps things exciting. On the flight here, I had the most fascinating conversation with this man from Bordeaux about how people outside the US consume so much of our political media. It’s been incredible.

Is this the same sort of hunch that took you on the 30 hour train rides?

Yes! I’ve always been fascinated by contained spaces like trains or planes. When you’re on a plane, I feel like psychologically, I get to a point where I’m like: “Okay, I am a woman of the plane now. And these are all my people.” The train is great to talk to strangers because the type of people who do 30-hour Amtrak rides are always fascinating. There’s a sense of community in that, even when it’s uncomfortable.

What does community mean to you?

The bottom line — and this is a fundamental belief of Hot Literati — is that people want to be connected to other people, no matter where they’re from. People are curious about people who are different from them.

When did Hot Literati start, and what inspired it?

If you had to pinpoint a moment, it would be roughly January of 2022. I was in Chicago doing research on the history of jazz clubs in the US for my thesis. I’ve always just read a ton — I love reading.

I posted one video about Cinderella Ate My Daughter by Peggy Orenstein, which is a book about girly-girl culture that I definitely grew up in and has affected the way I see the world. Overnight the video did a million and the account gained 60,000 followers.

I already had a modest following on Instagram because I did pageants growing up. But as the account grew, I realized the real value was in the discussions. I don’t love just saying what I think — I’m really curious about other people. The best moments happen when perspectives clash, and that’s when you build empathy. That’s why I really emphasized creating community out of it.

You’ve said critical thinking is core to Hot Literati. How do you define it?

To me, thinking is like letting ideas dance around your brain. To do it critically is maybe to do the dance multiple ways — balance a new perspective, pivot a couple times.

One of my goals with Hot Literati is to make critical thinking enjoyable. To think about something from a few different perspectives and then draw a conclusion. Because in today’s attention economy, not everyone has the privilege to slow down and do that — but when you do, it’s deeply rewarding.

Your “Flirty Fall” post really resonated. What does flirting mean in that context?

I have to acknowledge Anderson II, a really talented writer who wrote for Hot Literati last year. His definition of flirting is one I soaked up: it’s not necessarily about flirting with one person. It’s more like a way that you move throughout the world, where you’re prepared to be in love with anything at any point in time.

If you’re thinking about the work of your life, you have to do it — so you might as well see the plot in it, the beauty in it, and have fun. Flirting is fun.

What do Hot Literati events look like?

I have a personal rule — for better or worse, no two events are the same.

For example, at our “Love Island” event, people mingled and then split into groups to work on essays debating whether Love Island was good or bad for society. Keep in mind, drinks were offered throughout this, so it wasn’t just like class. Then each group presented. The winning group literally wrote down their argument — it was really funny. And two people actually hit it off that night. I hope they’re dating now.

What’s next for Hot Literati?

This fall I’m starting my first official writing workshops. I’ve done a lot of reading and self-discovery about what art means to me, and now I’m ready to share that philosophy.

Our next IRL book club event is in Chicago. It’s a Ballerina Fight Club where we will discuss Black Swan (2010) and Fight Club (1999) through the lens of Carl Jung's work on the shadow.

Also, my first book comes out this month — September 26! It’s titled Conditions of Hope, and it’s a collection of three short stories.

We’ll also continue our online book club, which I love because we have members everywhere from Barbados to Utah. The global mix makes it really special.

What a flirty fall! What do you hope to inspire in others throughout all this?

Honestly, I’d love to help others use the imagination muscle to see more opportunity in the world. To look at a stranger or a note on the ground and imagine a whole world around it.

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