We’re excited to introduce you to the always interesting and insightful Anna Popkov. We hope you’ll enjoy our conversation with Anna below.

Anna, thanks for taking the time to share your stories with us today Let’s kick things off with your mission – what is it and what’s the story behind why it’s your mission?

The mission of The Book of Boos and Boo Boos is to make dating more thoughtful and intentional, starting with the most important relationship—your relationship with yourself.

After a series of dead-end dates, I found myself asking, Is this it? Why can’t I make a connection stick? Despite having warm, lasting relationships with family and friends, romantic love felt out of reach. That disconnect led me to a deeper realization: dating isn’t just about finding the right person; it’s about understanding who you are, what you need, and why you’re seeking connection in the first place.

In conjunction with therapy and personal reflection, I created The Book of Boos and Boo Boos as a guided dating diary that feels like a friend—curious, honest, and supportive. It’s designed to help people face hard truths with compassion, embrace the journey with all its ups and downs, and ultimately uncover the love they already carry within themselves.

Our hope is simple: to inspire people to approach dating not as a destination, but as a meaningful process rooted in self-awareness, authenticity, and care.

Anna, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Since childhood, I’ve always been a storyteller—whether it was doodling, writing little plays to perform in the garage with neighborhood friends, or dreaming up characters and narratives. As I grew older, that creative spark never disappeared, but it often got tucked away in the “when I have time again” file. I’d been working on a novel for several years (it’ll be finished someday!), but when the idea for The Book of Boos and Boo Boos hit me, it felt different—urgent, inspired, and ready to come to life.

Drawing from my writing experience and years of absorbing relationship advice, I set out to create a guided dating diary that would feel thoughtful, engaging, and authentic. I originally planned to have a friend—an incredible artist—handle the illustrations. But after I sent her some of my own doodles to convey what I had in mind, she encouraged me to do the artwork myself. That unexpected push unlocked a whole new creative outlet. I started sketching the dating “types” by hand, then transitioned to digital art using Adobe Illustrator and Fresco—tools I’d never touched before. To my surprise, I loved every minute of it.

The idea for the diary was born in March 2023. I dove into it seriously that December, working on it daily, and by March 2024, I’d written, illustrated, and line-edited the entire book. After refining layouts, ordering samples from different manufacturers, and navigating rounds of tweaks (spending what felt like four months stuck at “98% done”), I finally held the finished product in my hands by September. The process was entirely new to me, and I’m incredibly proud of the timeline, the learning curve I climbed, and the beautiful final result. Even if someone never opens the book, its aesthetic stands on its own—but I hope they do open it because that’s where the real magic lives.

What might surprise people is the depth within its pages. Yes, The Book of Boos and Boo Boos has a playful name and some lighthearted, cheesy moments, but it’s also thoughtful, honest, and filled with heart. I didn’t create this book as someone claiming to have all the answers about love—I made it as someone still figuring it out, learning how to be kinder to myself along the way.

At its core, this diary is about connection—not just with others, but with ourselves. I believe if we sat in a room together, many of us would say, “Me too. I’ve felt that heartbreak, that rejection, that confusion.” But alongside those feelings, there’s beauty: the friend who’s seen you through every bad haircut, the stranger’s unexpected kindness, the sunsets we almost forget to notice. This diary is an invitation to hold space for all of it—the mess, the magic, and everything in between.

I’m still learning, and I hope this book helps others feel less alone on their own journey. Because at the end of the day, we’re all just trying to figure it out—and maybe we can do it a little better, together.

Do you think there is something that non-creatives might struggle to understand about your journey as a creative? Maybe you can shed some light?

I think people who think they fall into the non-creative category don’t realize how much of creative work is actual very non-creative. Margin spacing? Alignment? Font sizes? Paper grade? Shipping express, slow, mix of the two? One can look at a product and say, wow this is really creative, must have been a really fun journey without realizing how much mathematical and analytical minded skills are required to get something to the finish line.

For you, what’s the most rewarding aspect of being a creative?

As someone who is creative, I try to never take for granted the ability to look at any given thing and find beauty in it. It’s a skill we can all develop but life just opens up so much more when you look at it from a place of childlike wonder.

Contact Info:

• Website: https://thebookofboosandbooboos.com/
• Instagram: boosandbooboos
• Other: @thebookofboosandbooboos (TikTok)

Image Credits

Anna Popkov