The Intentional Alpha: From Financial Freedom to the Chaos of Modern Love (w/Ed)

Beyond the "Nice Guy": How To Build Authentic Confidence That Attracts (w/Jason L.)

Share your thoughts, or send in questions📝 [https://www.buzzsprout.com/2542818/fan_mail/new] If you’ve ever wondered why “being a good guy” still isn’t leading to the relationship you want, this conversation puts language to the problem and a roadmap to the solution. I sit down with Jason Lange, a men’s embodiment coach and certified No More Mr. Nice Guy coach, to talk about the quiet ways men lose themselves in dating: people-pleasing, hiding desire, avoiding tension, and trying to earn love by staying “easy” instead of being real. We break down Nice Guy Syndrome, the “man box” pressure to be invulnerable, and why so many men live from the neck up, then feel confused when partners ask for emotional presence. You’ll hear the difference between domination and relational leadership, plus a surprisingly useful tango metaphor for what attunement actually looks like. We also get practical about modern dating dynamics: how clear planning builds trust, why emotional leadership matters (especially around defining the relationship), and how men’s groups create the brotherhood, accountability, and nervous system resilience that makes intimacy easier at home.  If you want a healthier form of masculinity that includes both strength and heart, this one is for you. It is also a great episode for women to understand the challenges men face in dating! Find Jason here [https://evolutionary.men] Support the show [http://buymeacoffee.com/thedatingchit] 💖 Meet the host - Tongalag [https://linktr.ee/Tongalag] ☀️Apply to be a guest [https://thedatingchit.com/application] ☕️Take me out for a virtual coffee [http://buymeacoffee.com/thedatingchit]  ✨Social Media [https://linktr.ee/thedatingchit] 📝Share your thoughts, or send in questions! [https://www.buzzsprout.com/2542818/fan_mail/new]

The Intentional Alpha: From Financial Freedom to the Chaos of Modern Love (w/Ed)

Share your thoughts, or send in questions📝 [https://www.buzzsprout.com/2542818/fan_mail/new] I sit down with Ed, a Berkeley and Stanford trained engineer who had a startup exit ($8 Billion project), retired early, and is now rebuilding love after a long marriage while staying on great terms with his ex-wife. He is thoughtful, active, and honest about what it is like to re-enter online dating in midlife with real intention. We get into the stuff people usually avoid: when chemistry turns physical fast, how sex boundaries can protect trust, and why rushing into sex often clouds judgment for both men and women. We also talk about the modern breakup problem, ghosting and ending relationships through text, and how conflict avoidance shows up as avoidant attachment behaviors. We discuss self-awareness, the perfect label, anxious attachment and communications. Ed also shares the most surprising tools he is using right now: an AI dating coach and an attachment-focused AI journaling app that helped him uncover deeper patterns through Internal Family Systems style prompts.  We close with practical relationship advice. If you want more clarity in dating after divorce, better communication, and stronger emotional intelligence, you will get a lot from this conversation. Resources: 📗 Eight Dates by John Gottman [https://amzn.to/4tSHRWH] Support the show [http://buymeacoffee.com/thedatingchit] 💖 Meet the host - Tongalag [https://linktr.ee/Tongalag] ☀️Apply to be a guest [https://thedatingchit.com/application] ☕️Take me out for a virtual coffee [http://buymeacoffee.com/thedatingchit]  ✨Social Media [https://linktr.ee/thedatingchit] 📝Share your thoughts, or send in questions! [https://www.buzzsprout.com/2542818/fan_mail/new]

How A Great Matchmaker Sees Compatibility, Insights From Matching Thousands of Couples (w/Dara Rahill)

Share your thoughts, or send in questions📝 [https://www.buzzsprout.com/2542818/fan_mail/new] Today, I am joined by Dara Rahill, a former top-ranked premium matchmaker at the country's largest matchmaking platform, and now the founder of Dara Rae Matchmaking, to reveal what actually predicts a healthy long-term relationship when you look beyond photos, height filters, and perfect-on-paper stats.  We dig into the behind-the-scenes reality of modern dating:  “checklists”, dating profiles, and how dating app culture amplifies snap judgments.  Dara explains how real compatibility is assessed, plus the intuitive “art” a matchmaker develops after interviewing thousands of singles. We also unpack why even highly sought-after people sometimes choose high-end matchmaking services. One of the most eye-opening parts is who can be hardest to match and why. We also challenge the myth of instant chemistry, exploring how attraction can grow through repeated exposure. If you’re tired of guessing, lower-stakes clarity starts here. Great episode for both men and women. 🎀 Dara Rae Matchmaking [https://www.dararaematchmaking.com/] 🫶 Dara Rae Instagram [https://www.instagram.com/dararaematchmaking/] Support the show [http://buymeacoffee.com/thedatingchit] 💖 Meet the host - Tongalag [https://linktr.ee/Tongalag] ☀️Apply to be a guest [https://thedatingchit.com/application] ☕️Take me out for a virtual coffee [http://buymeacoffee.com/thedatingchit]  ✨Social Media [https://linktr.ee/thedatingchit] 📝Share your thoughts, or send in questions! [https://www.buzzsprout.com/2542818/fan_mail/new]

What Dating Bay Area Engineers Really Feels Like (w/Violina)

Share your thoughts, or send in questions📝 [https://www.buzzsprout.com/2542818/fan_mail/new] Dating a Bay Area engineer can look perfect on paper… but feel unexpectedly lonely in real life. In this episode, we get brutally honest about what it’s actually like dating engineers in Silicon Valley—the parts that feel safe and stable, and the parts that quietly hurt. Violina is back, and we’re sharing real stories, unpacking patterns we kept running into, and reflecting on the moments that led to some big realizations. We also talk about the green flags—what draws so many people to engineers in the first place—and why those same traits can sometimes create disconnect in relationships. This is about understanding what works, what doesn’t, and what actually matters in the long run. If you’ve ever felt like you’re dating someone who tries to debug emotions instead of actually feeling them, this conversation will hit home. Whether you’re dating in the Bay Area, seeing a software engineer, or you are an engineer wanting to understand how this dynamic can land, this episode offers clarity—and some practical questions you’ll wish you had asked earlier. Support the show [http://buymeacoffee.com/thedatingchit] 💖 Meet the host - Tongalag [https://linktr.ee/Tongalag] ☀️Apply to be a guest [https://thedatingchit.com/application] ☕️Take me out for a virtual coffee [http://buymeacoffee.com/thedatingchit]  ✨Social Media [https://linktr.ee/thedatingchit] 📝Share your thoughts, or send in questions! [https://www.buzzsprout.com/2542818/fan_mail/new]

Bay Area Alert!! A Growing Number of Men Are Quietly Avoiding Dating Here - Why? (w/Mike)

Share your thoughts, or send in questions📝 [https://www.buzzsprout.com/2542818/fan_mail/new] In this episode, we explore dating situations in the Bay Area, why some single men are not feeling great about it, and what happens when someone changes their dating “ecosystem.”  My guest Mike—a thoughtful, twice-divorced tech professional who took five years to reset after his marriages—shares how he approaches dating today. We talk about the reality of swiping, slow replies, and the quiet chase for the “top 1%,” and how these dynamics can make dating feel harder than it needs to be. Mike also shares an interesting experiment: changing his dating locations from San Francisco to places like Chicago and Southeast Asia. Along the way, we unpack what truly predicts compatibility beyond checklists.  This conversation invites both men and women to rethink their strategy: maybe the issue isn’t that good partners don’t exist, but that the environment—and how we approach it—needs a reset. Support the show [http://buymeacoffee.com/thedatingchit] 💖 Meet the host - Tongalag [https://linktr.ee/Tongalag] ☀️Apply to be a guest [https://thedatingchit.com/application] ☕️Take me out for a virtual coffee [http://buymeacoffee.com/thedatingchit]  ✨Social Media [https://linktr.ee/thedatingchit] 📝Share your thoughts, or send in questions! [https://www.buzzsprout.com/2542818/fan_mail/new]