Relationship anxiety does not disappear once the dating stage ends. Sometimes it shows up as planning, comparison, excitement, or constantly thinking about the next milestone.

Lilly Wehman and Amelia Abernathy talk honestly about engagement anticipation, the pressure to seem like the “cool girl,” and how difficult it can be to stay present when the future feels close enough to imagine. They also share practical ways to slow down, communicate what is happening, and approach anxious thoughts with curiosity instead of criticism.

Key Topics

• Why anxiety can continue in established relationships
• Imagining the wedding versus imagining the marriage
• Engagement anticipation and the discomfort of waiting
• Planning as a way to manage uncertainty
• The pressure to act chill or unbothered
• The difference between validation and comparison
• Staying present during relationship transitions
• Communicating fears, expectations, and boundaries
• Using journaling, mindfulness, movement, and friendships to slow down
• Giving yourself grace when experiencing something new

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 Series: Relationship Milestones That Matter
• Dating in Your 20s: Prioritizing Mental Health While Dating

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

Lilly Wehman and Amelia Abernathy use the Summer House Season 10 drama to talk about self-worth, friendship breakups, and what happens when someone moves from one relationship into the next without slowing down. They look at Ciara, Amanda, West, and Kyle through a therapist lens without trying to diagnose anyone.

The conversation moves through staying friends with exes, wanting to be the “cool girl,” the pain of being hurt by a close friend, and the difference between finding your spark through someone else versus rebuilding it for yourself.

Key Topics

• Summer House Season 10 through a therapist lens
• Staying friends with an ex
• The pressure to seem unbothered after a breakup
• Friendship breakups and betrayal
• Self-worth after a hard relationship
• Finding yourself outside of dating
• The difference between soothing and solving

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 20s Shift: Outgrowing, Holding On, and Becoming
• The Honeymoon Phase: Butterflies or Just Anxiety?

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

In this episode, Lilly Wehman and Amelia Abernathy explore what it means to date while navigating a chronic illness. Through personal storytelling and a therapeutic lens, they unpack the realities of vulnerability, disclosure, and identity in relationships. The conversation highlights the emotional complexity of managing health challenges while dating, the impact of uncertainty on connection, and the role of therapy and support systems in building grounded, authentic relationships.

Key Topics

• Dating while navigating a chronic illness
• Vulnerability and the timing of disclosure
• Identity shifts and loss of control
• The emotional impact of ghosting and rejection
• The role of therapy and external support
• Building relationships rooted in authenticity

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:

• Is ‘The One’ Even Real? Unpacking Soulmate Myths and Dating with Intention
• The Honeymoon Phase: Butterflies or Just Anxiety?

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

In this episode, Amelia Abernathy and Lilly Wehman explore the evolving nature of friendships, relationships, and identity in your 20s. Through an honest and reflective conversation, they unpack how life transitions—dating, career shifts, and personal growth—reshape social dynamics and emotional connections. This episode highlights the tension between holding on and letting go, while offering a grounded perspective on navigating change with self-awareness and compassion.

Key Topics

• The evolution of friendships in your 20s
• How romantic relationships impact social dynamics
• Navigating shifting priorities and identity development
• Emotional attachment, comparison, and change
• Self-reflection as a tool for growth
• Letting go without guilt or resentment

Takeaways

• Change in your 20s is inevitable—and often necessary for growth
• Friendships can evolve without needing to end
• Open, honest communication strengthens relationships during transitions
• Self-awareness allows for more grounded, intentional connections
• Growth often requires redefining emotional and social priorities
• Compassion for yourself and others is key during periods of change

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:

• Why Do I Always Start Fights? A 20s Guide to Conflict Styles
• What to Do When You’re the Last Single One

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

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

In this episode, Amelia and Lilly dive into the idea of personal growth through relationships—how every connection, whether positive or painful, can become a mirror for self-development. Lilly shares her reflections on learning to recognize and celebrate growth, emphasizing the importance of honoring both the messy and meaningful parts of the journey. Together, they unpack how relationships shape who we become and why self-celebration is an essential, often overlooked, part of healing and growth.

Takeaways

• Even negative experiences can spark growth.
• Positive relationships also teach us valuable lessons.
• Celebrating your own growth is essential to healing.
• Growth isn’t linear—it’s circular, layered, and evolving.
• Recognizing growth moments fosters self-pride and self-awareness.
• Relationships reflect our patterns, progress, and potential.
• Growth means honoring both challenges and achievements.

Related Episodes:

• The Ten Commandments
• Why You Ghost, Cling, or Chase: Attachment Styles with Hilary Rosenberg

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