Why Dating Feels Complicated

Most people aren’t bad at dating, they’re just trying to solve the wrong problem. We treat dating like a personality test (“Am I attractive enough? Confident enough?”) when it’s actually a multi-stage process, and each stage punishes completely different mistakes. That one misunderstanding explains why dating feels so confusing, why men and women keep blaming each other, why dating apps feel brutal, and why so much dating advice makes things worse instead of better.

In this episode of Solved, Drew and I break down why modern dating feels so broken, and why it actually isn’t. We dig into the evolutionary psychology behind attraction, why men and women are optimizing for different things, how modern culture and dating apps amplify the worst parts of the system, and the three stages of dating that almost nobody understands. We also talk about confidence, rejection, status, attraction, and why avoiding rejection is often the very thing sabotaging your dating life. If you’ve felt stuck, burned out, or quietly wondering “what the hell is wrong with dating?” — this episode is for you.

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Chapters:

0:00 Introduction

5:12 Chapter 1: Why Is Dating So Complicated?

11:03 The different challenges men and women face

17:18 Facts

29:51 What Women Find Attractive

38:16 What Men Find Attractive

51:27 Chapter 2: A Brief History of Courtship & Dating

1:06:10 Modern Dating

1:11:41 A Glimmer of Hope: The emerging offline renaissance

1:21:37 Chapter 3: Men's and Women's Dating Advice Ecosystems

1:31:13 Inside the Male Advice Ecosystem

1:44:52 Inside the Female Advice Ecosystem

2:02:07 The Collision: Feedback Loops That Break the Market

2:21:27 Chapter 4: The Pre-Dating Phase

2:36:22 Building Confidence

2:37:59 Halo Effect

2:53:20 Conclusion Pre Dating

2:57:48 Chapter 5: Meeting People and Getting Dates

3:11:17 Flirting

3:23:15 Reading People

3:29:51 Chapter 6: Going on Dates

3:38:39 Trustworthiness

3:47:09 Conversational Skills

3:56:12 Emotional Regulation

4:03:03 Boundaries

4:09:07 F**k yes or no

4:14:44 The 80/20

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