105. Dating Advice I Wish I Knew with the Almost 30 Podcast

Today on Flirtations, we welcome Krista Williams and Lindsey Simcik, the powerhouse due behind the Almost 30 podcast, with over 100M downloads around the world, and authors of the new book Almost 30:  A Definitive Guide to a Life You Love for the Next Decade and Beyond, who are here to have a conversation with us today about dating advice I wish I knew!

We open with the interplay between change and fear, and how can we navigate the space of change and life's experiences without holding ourselves back? Or self sabotaging?

We also explore hyperindividualism and codependency in dating and relationships, how each manifests and what we can do if we fall into these dynamics?

But that’s not all, we’re going to talk about the duality of loneliness and healing, self-love and how to find the right balance between just enough and feeling like it’s never enough, and, if you’re dating the mens, but kind of can’t stand them either, we’ll hear how to begin reframing relationships with men.

Alright Flirties, if you’re read for a heartfelt and transformative episode, this one is for you!

Now let’s meet Krista and Lindsey!

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About our guests:  Lindsey Simcik and Krista Williams, founders and co-hosts of the popular “Almost 30” podcast, are women’s empowerment leaders and best friends releasing their debut book “Almost 30: A Definitive Guide to a Life You Love for the Next Decade and Beyond,” on June 3, 2025. Part memoir, part manual, fans are eagerly awaiting the book as their ultimate guide to navigating life’s transitions.

In the “Almost 30” book, Lindsey and Krista act as cosmic big sisters, providing encouragement, wisdom, and practical tools to help readers embrace change and thrive and they move into a new chapter of life. Through candid stories of their own experiences, as well as expert insight from podcast guests like Jay Shetty, Gabby Bernstein, and Glennon Doyle, Lindsey and Krista lay out a roadmap for navigating young adulthood, from relationships to spirituality, career to body image, and more.  

Packed with thought-provoking exercises, meditation and journaling prompts, and sage advice, this book is a must-have companion for anyone standing at the edge of change. Whether you’re figuring out who you are or where you’re going next, “Almost 30” is here to guide you through life’s transitions and remind us that we’re all almost… something.

The “Almost 30” podcast is a top wellness, spirituality, and self-development podcast. Since the show’s inception, Lindsey and Krista have amassed over 100M downloads, completed a 13-city tour, hosted in-person retreats and online workshops, and built an online membership community platform.

Lindsey Simcik is a content creator, author, and co-host of the successful “Almost 30” podcast. Recently having become a first-time mother, Lindsey is a mainstay lifestyle creator for moms and anyone seeking to live a natural, holistic life.

Krista Williams is a content creator, author, and co-host of the successful “Almost 30” podcast. Known for her style and vibrancy, followers flock to Krista for dating, travel and self-care inspiration.

You can learn more and purchase a copy of the "Almost 30" book wherever books are sold!

About your host:  Benjamin is a flirt and dating coach sharing his love of flirting and BFE - big flirt energy - with the world! A lifelong introvert and socially anxious member of society, Benjamin now helps singles and daters alike flirt with more confidence, clarity, and fun!

As the flirt is all about connection, Benjamin helps the flirt community (the Flirties!) date from a place that allows the value of connection in all forms - platonic, romantic, and with the self - to take center stage.

Ultimately, this practice of connection helps flirters and daters alike create stronger relationships, transcend limiting beliefs, and develop an unwavering love for the self.

His work has been featured in Fortune, NBC News, The Huffington Post, and Yoga Journal.

You can connect with Benjamin on Instagram, TikTok, stream the Flirtations Flirtcast everywhere you listen to podcasts (like right here!), and find out more about working together 1:1 here.