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.
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This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit:
millenniumhope.comWhat is Dating in Your 20s?
Hosted by Amelia and Lilly, two licensed therapists based in Chicago, Illinois, Dating in Your 20s dives into the chaos, comedy, and complexity of modern dating — all through a therapeutic lens. As two women in their 20s, Amelia and Lilly are in the trenches themselves, navigating everything from bad Hinge dates and ghosting to social media comparison and the pressure of modern relationships.
With a mix of humor, honesty, and clinical insight, each episode blends real-life dating experiences with psychological frameworks like attachment theory, emotional regulation, communication styles, and more. Whether you're healing from heartbreak, stuck in a situationship, or just wondering why dating feels so complicated right now, Amelia and Lilly are here to help you feel a little less alone — and a lot more understood.