Dating in Your 20s

Amelia Abernathy & Lilly Wehman
  • 5.0 (2)
  • MENTAL HEALTH
  • UPDATED WEEKLY

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.

  1. 3D AGO

    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 datingThe fears and insecurities that follow us through our twentiesFriendship as a foundation for personal and relational growthRecognizing unhealthy dating patterns and taking accountabilityThe moment you realize growth starts withinLetting go of timelines and expectations around love and relationshipsWhy 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 BuildIs 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 | LinkedInAmelia Abernathy: Millennium | LinkedIn This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

    34 min

  2. 12/11/2025

    The “Village” We Romanticize vs. the Village We Actually Build

    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 20sThe pressure to “protect your peace” and how it impacts connectionEmotional labor as an investment, not a burdenReciprocity vs. scorekeepingWhy crisis moments don’t build friendship — consistency doesLosing friends, outgrowing friends, and navigating changing dynamicsBeing a “villager”: how to actually show up for your peopleThe small, mundane moments that make friendships feel safeUnderstanding 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 MattesonDating 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 | LinkedInAmelia Abernathy: Millennium | LinkedIn This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

    24 min

  3. 12/04/2025

    Is Having a Boyfriend Embarrassing?

    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 PastThe Crash-out EpisodeDating 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 | LinkedInAmelia Abernathy: Millennium | LinkedIn This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

    35 min

  4. 11/13/2025

    Self-Celebration Isn't Selfish

    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 CommandmentsWhy You Ghost, Cling, or Chase: Attachment Styles with Hilary RosenbergDating 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 | LinkedInAmelia Abernathy: Millennium | LinkedIn This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

    31 min

  5. 11/06/2025

    The Ten Commandments

    In this episode, Amelia and Lilly recap their time at the Beauty Boost Chicago event and reflect on the power of community and supporting local businesses. They revisit the mission behind their podcast — offering a therapeutic lens on dating and relationships — and dive into the “unwritten rules” of modern dating. Together, they question these societal commandments, encouraging listeners to decenter external expectations and reconnect with their own values. The conversation touches on navigating feedback from friends and family, the messy process of self-discovery in your 20s, and practicing compassionate curiosity toward yourself and others. Amelia and Lilly close with a reminder that there’s no single “right” way to date — just your way — and invite listeners to embrace their unique experiences and seek support along the journey. Takeaways The Beauty Boost Chicago event showcased local businesses and communities.Listeners appreciate the therapeutic approach to dating discussed in the podcast.Societal rules around dating can create unnecessary pressure.It's important to focus on personal values rather than external expectations.Feedback from friends and family can complicate dating decisions.Self-discovery is a crucial part of navigating relationships in your 20s.Embracing change is essential for personal growth.Compassionate curiosity helps in understanding oneself better.It's okay to feel uncomfortable when spending time alone.The journey of dating is unique for everyone, and there's no one-size-fits-all approach.Related Episodes: The Crash-out EpisodeLooking Back, Moving Forward: How Our Podcast Changed Our Relationships With Oren MattesonDating 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 | LinkedInAmelia Abernathy: Millennium | LinkedIn This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

    30 min

  6. 10/16/2025

    The Crash-out Episode

    In this episode of 'Dating in Your 20s', therapists Lilly Wehman and Amelia Abernathy share their personal experiences and insights on the emotional challenges of dating in their twenties. They discuss the vulnerability of early dating stages, the extremes of emotional responses, and the importance of community and shared experiences. The conversation emphasizes the need for coping mechanisms and small steps to regain control amidst the chaos of dating, while also promoting an upcoming community event for listeners. Takeaways Clients are experiencing heightened anxiety over dating responses.Vulnerability is a common theme in early dating stages.Jumping to conclusions can lead to unnecessary anxiety.Communication is key to avoiding ghosting.Finding balance between extremes is essential for emotional health.The middle ground in dating can be a safe space.Coping mechanisms can be small but effective.Community support is vital during dating struggles.It's okay to seek help and share experiences with others.Link to the event we’ll be at: https://www.thebeautyboost.net/events/sip-social-spook Related Episodes: Looking Back, Moving Forward: How Our Podcast Changed Our Relationships With Oren MattesonPutting Yourself Out There (Ugh) The brave act of dating with anxietyDating 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 | LinkedInAmelia Abernathy: Millennium | LinkedIn This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

    30 min

  7. 10/09/2025

    Looking Back, Moving Forward: How Our Podcast Changed Our Relationships With Oren Matteson

    In this episode, Oren Matteson sits down with Dating in Your 20s hosts Amelia Abernathy and Lilly Wehman to reflect on their podcast journey so far. Together, they explore how their conversations about dating, growth, and self-awareness have shaped their own relationships and perspectives. The trio dives into topics like communication, setting intentions, evolving expectations in modern dating, and what commitment really looks like in your twenties. They also share what’s next for the podcast and how it continues to evolve alongside their personal lives. Takeaways The podcast started as a resource for clients.Lilly and Amelia's relationship has deepened through their discussions.The podcast has helped them connect with friends and clients.Amelia feels less different in her dating experiences.Conversations on the podcast have made them more confident.Dating is seen as fun and exciting, not embarrassing.Expectations in dating are influenced by media and societal norms.Communication is key to understanding intentions in dating.Commitment is a signal to begin the hard work in relationships.They aspire to create more interactive content for their audience.Related Episodes: The Narcissism Conversation: What’s Real, What’s Overused, and How to Heal With DeVona AlleyneDating in Your 20s Series: Male Perspectives on Dating with Oren MattesonDating 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 | LinkedInAmelia Abernathy: Millennium | LinkedInOren Matteson: Millennium | LinkedIn This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

    31 min

  8. 10/02/2025

    The Narcissism Conversation: What’s Real, What’s Overused, and How to Heal With DeVona Alleyne

    In this episode of Dating in Your 20s, Amelia and Lilly sit down with Rev. DeVona Alleyne, LCPC, Clinical Director at Millennium Counseling Center, for a candid conversation about the complexities of narcissism in relationships. Together, they break down: The traits of narcissistic tendencies and how they can show up in datingThe phenomenon of love bombing and its emotional aftermathThe role of gaslighting and why it can be so disorientingHow to recognize red flags and set boundariesThe importance of self-awareness and compassion—for both yourself and othersDeVona shares wisdom from her clinical perspective and pastoral lens, offering guidance on how to protect your mental and emotional health while navigating the highs and lows of dating in your 20s. This episode is an honest and empowering look at how to prioritize your needs, trust your instincts, and approach relationships with clarity and confidence. Takeaways Narcissistic tendencies can manifest as a lack of empathy.Love bombing often covers up underlying shame.Recognizing red flags early can prevent emotional turmoil.Gaslighting is a common tactic used by narcissists.Setting boundaries is crucial in any relationship.Compassion for those with narcissistic tendencies is important.Attachment styles can influence relationship dynamics.Dating in your 20s requires self-awareness and reflection.It's essential to prioritize your own needs in relationships.Healthy relationships should allow for personal boundaries. Related Episodes: The DMs Are Open: Listener Q&AWhy You Ghost, Cling, or Chase: Attachment Styles with Hilary RosenbergDating 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 | LinkedInAmelia Abernathy: Millennium | LinkedInRev. DeVona Alleyne: Millennium | LinkedIn This podcast is powered by Millennium Counseling Center in Chicago, IL. To learn more visit: millenniumhope.com

    36 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

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.

Information

  • Creator
    Amelia Abernathy & Lilly Wehman
  • Years Active
    2025 - 2026
  • Episodes
    20
  • Rating
    Clean
  • Copyright
    © 2026 Amelia Abernathy & Lilly Wehman
  • Show Website
    Dating in Your 20s