Most people think they have a dating problem. What they actually have is a pattern problem.
We don’t just choose partners. We choose familiarity. And for a lot of people, that means unconsciously chasing the same emotional experience over and over again. The hot-and-cold dynamic. The anxiety. The longing. The feeling of having to earn love instead of safely receiving it.
Relationship expert and bestselling author Amy Chan explains why so many people keep falling for unavailable partners, confusing chemistry with compatibility, and mistaking chaos for passion. Because the truth is, healthy love often feels unfamiliar before it feels safe.
This conversation goes far deeper than dating advice. Amy breaks down the psychology behind limerence, nervous system activation, repetition compulsion, and why people unconsciously recreate the emotional wounds they experienced in childhood. She shares the exact patterns that quietly sabotage relationships, the role inconsistency plays in triggering anxiety, and why stable love can initially feel “boring” to people conditioned by unpredictability.
Matt and Amy also unpack modern dating culture, the pressure created by social media expectations, and the dangerous advice being normalized online. Together, they explore what actually creates lasting love: commitment, mutuality, emotional safety, integrity, and the willingness to work through discomfort instead of running from it.
Amy opens up vulnerably about her own relationship patterns, the years she spent chasing emotionally unavailable people, and the personal breakthrough that finally changed everything. The result is a masterclass on love, attachment, healing, friendship, emotional maturity, and what it truly means to build relationships that last.
If you’ve ever wondered why dating feels exhausting, why you keep repeating the same patterns, or what healthy love is actually supposed to feel like, this episode will change the way you see relationships forever.
UnSingle: The Art of Loving Yourself, Building Healthy Relationships, and Dating Smarter
Amy's website (bootcamps + more fun!)
In this episode you will:
Discover why people unconsciously recreate familiar emotional wounds in relationships and how childhood experiences quietly shape who you’re attracted to Learn the difference between chemistry and compatibility and why confusing the two leads so many people into unhealthy relationships Understand why inconsistency and hot-and-cold behavior activate anxiety in the nervous system and what emotionally safe love actually feels like Break down the four pillars of a healthy relationship: chemistry, compatibility, timing, and mutuality Explore the psychology of limerence, chasing, and emotional addiction and why some people become attached to the pursuit of love more than love itself Learn why healthy relationships can initially feel “boring” to people conditioned by chaos, unpredictability, or emotional instability Understand the role commitment plays in long-term love and why feelings alone are never enough to sustain a relationship Discover the difference between wanting love and having the capacity and ability to maintain a healthy relationship Learn practical ways to create deeper intimacy, emotional safety, and lasting connection inside long-term relationships Hear Amy’s framework for building “relational wealth” through nourishing friendships, meaningful community, and intentional human connection