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:

• The “Village” We Romanticize vs. the Village We Actually Build
• Is Having a Boyfriend Embarrassing?

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

Your 20s are basically one ongoing identity crisis — dating feels confusing, friendships feel different than they used to, and everyone seems to be overwhelmed, healing, or “protecting their peace.” In this episode, Amelia and Lilly talk about one of the most underrated parts of dating in your 20s: the people around you matter just as much as the person you’re dating.

This is a conversation about friendship, emotional labor, reciprocity, and what it actually means to build a village — not just want one. Because the truth is, friendships in your 20s don’t happen by accident. They take intention, vulnerability, and a willingness to show up even on the days you’d rather hide under a blanket.

If dating is about who you’re becoming, then friendship is the support system that gets you there.

Takeaways

• Why friendships feel harder to maintain in your 20s
• The pressure to “protect your peace” and how it impacts connection
• Emotional labor as an investment, not a burden
• Reciprocity vs. scorekeeping
• Why crisis moments don’t build friendship — consistency does
• Losing friends, outgrowing friends, and navigating changing dynamics
• Being a “villager”: how to actually show up for your people
• The small, mundane moments that make friendships feel safe
• Understanding when someone can’t show up (and when it’s a pattern)

Related Episodes:

• Is Having a Boyfriend Embarrassing?
• Looking Back, Moving Forward: How Our Podcast Changed Our Relationships With Oren Matteson

Dating In Your 20s Anonymous Corner

We’d love to hear from you! 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

In today’s dating culture, where everyone is either soft launching, situationshipping, or pretending they don’t care…it almost feels controversial to say you have a boyfriend. Thanks to a recent Vogue article making its rounds, Amelia and Lilly dive into the very real (and very funny) question:

Is having a boyfriend… embarrassing now?

This episode unpacks the weird social pressure young women feel in their 20s: wanting connection, craving independence, and also low-key worrying that posting your boyfriend will ruin your mysterious internet aura.

The hosts break down the cultural shift they’re seeing everywhere: independence is trending, relationships are treated like an aesthetic choice, and the internet has definitely influenced how we feel about commitment.

The Real Takeaway

This Vogue debate isn’t really about boyfriends — it’s about how much pressure we put on ourselves in our 20s to look a certain way, date a certain way, or be single a certain way. The goal?

Do whatever feels right for your life, not your feed.

Takeaways

• Relationship culture has changed — independence is trendy, and commitment gets weirdly judged.
• Social media shapes how we think our love lives “should” look.
• Whether you’re single, cuffed, or somewhere in-between, your identity doesn’t disappear.
• Being in a relationship isn’t embarrassing — pretending you don’t want connection might be.

Related Episodes:

• Ghosts of Boyfriends Past
• The Crash-out Episode

Dating In Your 20s Anonymous Corner

We’d love to hear from you! 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