Everything I Know About Dating in Your 20s

In this episode of Dating In Your 20s, Amelia sits down with Lilly to unpack the lessons, heartbreaks, and reality checks that shape so many of our dating experiences in our twenties. Inspired by Dolly Alderton’s book Everything I Know About Love, the conversation explores how dating, friendships, and self-discovery are deeply intertwined during this decade.

Together, Amelia and Lilly dive into the fears and insecurities that surface while navigating relationships, situationships, and the pressure to have it all figured out. They also reflect on the humbling moments when we realize that sometimes it’s not the world that needs changing — it’s our own patterns, expectations, or healing that deserve attention.

This episode is an honest conversation about growth, accountability, friendship, heartbreak, and learning to love yourself before chasing love from someone else. If you’ve ever wondered why dating feels so complicated in your twenties, or found yourself repeating the same relationship cycles, this episode is for you.

In this episode, they discuss:

Lessons from Everything I Know About Love and how they show up in modern dating
The fears and insecurities that follow us through our twenties
Friendship as a foundation for personal and relational growth
Recognizing unhealthy dating patterns and taking accountability
The moment you realize growth starts within
Letting go of timelines and expectations around love and relationships
Why self-awareness matters more than finding “the one”

Takeaway

Your twenties are less about finding the perfect partner and more about becoming someone you’re proud to be with — and learning along the way that love shows up in many forms, not just romantic ones.

Join the conversation:

What is something dating in your twenties has taught you about yourself? Share your thoughts and stories with us — we’d love to hear them.

Related Episodes:

Dating In Your 20s Anonymous Corner

Check out the anonymous DIY20s Form. It’s a safe, judgment-free space to share what’s going on in your love life.

Connect:

Lilly Wehman: Millennium | LinkedIn
Amelia Abernathy: Millennium | LinkedIn

This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

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