Jonathon Aslay (he/him)

Jonathon Aslay joined Momma on August 3, 2026 for a live Q&A via Twitch and YouTube to talk about Overcoming Adversity & Dating After Divorce

About Jonathon 

The focus of one of America's Leading Mid-Life Self-Love/Relationship coaches has expanded into a deeper, essential philosophy of what it truly means to LOVE.  After losing his 19-year-old son Connor in 2018, Jonathon Aslay’s grief led him on a soul-searching inner journey, where he became aware of an often-overlooked dimension of the dating conversation. He realized that the relationship process reveals the most common emotional health issue faced by many singles seeking a partner: a distressing lack of self-worth, self-regard, and self-love. Today, he is on a mission to encourage both men and women to fully love themselves with his book, "What The Heck Is Self-Love Anyway?"—packed with fun, engaging spiritual and personal growth practices.

Socials / Links for Guest Connection

• Website - https://www.jonathonaslay.com/

• Facebook - https://www.facebook.com/jonathon.aslay

• YouTube - https://www.youtube.com/@JonathonAslay

• Instagram - https://www.instagram.com/jonathonaslay/

• LinkedIn - https://www.linkedin.com/in/jaslay/

• TikTok - https://www.tiktok.com/@jonathonaslay?lang=en

References / Things Mentioned During the Stream

• Movie Recommendations

  • The Secret 

  • Good Will Hunting 

  • When Harry Met Sally... 

  • Wall Street 

  • Meet the Robinsons 

• Book Recommendations

  • A Course in Miracles

  • A Return to Love: Reflections on the Principles of "A Course in Miracles" by Marianne Williamson 

  • Alice in Wonderland by Lewis Carroll 

  • Eight Dates 

  • If the Buddha Dated: A Handbook for Finding Love on a Spiritual Path by Charlotte Kasl 

  • The Untethered Soul: The Journey Beyond Yourself by Michael A. Singer 

  • Attached: The New Science of Adult Attachment and How It Can Help You Find—and Keep—Love by Amir Levine, Rachel Heller 

  • Existential Kink: Unmask Your Shadow and Embrace Your Power by Carolyn Elliott 

• The Hoffman Process

• The Insight Institute 

• {The And} Relationship Card Game

• Anxious vs Avoidant Attachment: Key Signs, Differences, and Common Questions 

• Favorite Poem (song): You Can't Get What You Want (Till You Know What You Want) by Joe Jackson 

Episode Summary

For anyone dating again after divorce, grieving a loss or starting over somewhere they never planned to be, Jonathon Aslay brings blunt advice, a hundred first dates’ worth of lessons and zero interest in sugarcoating any of it.

Dating after divorce is messy, and a lot of us jump in without ever learning to love ourselves first. On this episode of Even Tacos Fall Apart, I sit down with Jonathon Aslay, a midlife self-love and relationship coach, to talk about overcoming adversity, rebuilding trust in yourself and dating again when your life looks nothing like you planned.

Jonathon was 40 when a divorce and the loss of a high-end job dropped him into the dating pool. He went on around a hundred internet dates in his first year and figured out that whatever felt off every time was him. That became a coaching career, starting with women asking him to read their dating profiles from a man’s point of view. He explains how swipe apps changed dating and why they make it easy to find a hookup and hard to find an emotionally healthy person.

Jonathon is open about the hard parts. After his divorce, his job loss and the 2008 crash, he spent about four years going to bed wishing he wouldn’t wake up, and he credits a simple phrase, keep moving forward, with getting him through. In 2018 he lost his son Connor, and he shares what it meant to choose to grieve with love instead of suffering and how gratitude became the through line of his life. He talks about the therapy and workshops that built what he calls emotional scaffolding, and about using psychedelics to feel connected to Connor and work through fear, guilt and shame. It took him about 20 years to get ready for the relationship he has now.

Then we get into the practical stuff for dating after divorce or after 40. Jonathon says you’re ready when your desire, capacity and vision for a relationship outweigh your past hurts, fears and fantasies. He calls it being committed to commitment. We cover what mature love looks like (attention, affection, appreciation and acceptance, with both people giving equally), why three to six months of regular time together is enough to know if love will show up and why real questions, honest talk about your past and owning your part all matter. The red flag people ignore most is the person who throws every ex under the bus.

He also tells a great story about a Halloween first date that changed how he thinks about who pays the bill, and how he met his partner. She messaged him on three different dating apps before it clicked, and they became friends over marathon phone calls long before the first kiss.

We wrap up with what self-love looks like as a daily practice, why he sends love to every profile he swipes left on and his magic wand wish for mental health: getting rid of judgment. He also shares a reading list that includes Eight Dates, Attached, If the Buddha Dated and The Untethered Soul.