21 The Dating Mistakes Every Man Makes. The American Masculinity podcast

2d ago 1:00:51

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Dating in 2025 asks more of men than ever before. Apps can feel like a grind, rejection hits hard, and old scripts like “the man should always pay” don’t always fit.

In this episode of American Masculinity, Tim sits down with Damien Diecke, Founder & Head Coach of the School of Attraction, to talk about what actually helps men thrive in today’s dating world. Damien’s coaching emphasizes presence over performance, empathy over pressure, and real-world skills over gimmicks.

Full Show Notes: www.americanmasculinity.com

Connect with Damien: https://schoolofattraction.com/

Tim's Episode on School of Attraction: https://open.spotify.com/episode/1j2yZPowYrLzS62VkIzuEp?si=8394be6f489148da

In this conversation:

How men can reframe rejection as practice, not failure
Why subtle indicators of interest matter more than lines
What the data actually says about who pays on the first date
How to move from apps to in-person connections
Why authentic masculinity looks less like control, and more like presence

Damien brings years of coaching experience and a commitment to helping men date with maturity and integrity. Whether you’re on the apps, out in the real world, or just trying to build confidence, this episode will give you tools that work without the gimmicks.

👉 After listening, tell us in the episode survey: What dating script are you updating this year — paying, reading signals, or handling rejection differently?

The American Masculinity Podcast™ is hosted by Timothy Wienecke — licensed psychotherapist, Air Force veteran, and men’s advocate.
Real conversations about masculinity, mental health, growth, and how men can show up better — as partners, leaders, and friends.
We focus on grounded tools, not yelling or clichés. If you have questions or want a tool for something you're wrestling with, leave a comment or send a message — your feedback shapes what we build next.
Note: While this doesn’t replace therapy, it might help you notice something worth exploring.

Chapters

1. Cold Open (00:00:00)

2. Meet Damien Diecke (00:02:00)

3. The Biggest Dating Mistakes Men Make (00:05:30)

4. Reading Real-World Interest Signals (00:12:15)

5. Reframing Rejection as Practice (00:18:45)

6. Who Pays on the First Date? (2025 Data) (00:25:20)

7. Building Presence vs. Performance (00:32:10)

8. Apps vs. Real-World Social Skills (00:38:30)

9. Practical Dating Scripts That Work (00:44:15)

10. Wrap-Up & Key Takeaways (00:50:00)

25 episodes