Dating, Solved: Why Finding the “Right Person” Feels So Hard Now
Wed Feb 04 2026
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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We also put together a free companion guide for this episode with all the takeaways, references, and tools to help you get your sh*t together once and for all. Download it here: https://solvedpodcast.com/dating
Sign up for my newsletter, Your Next Breakthrough. It will help make you a less awful person: https://markmanson.net/breakthrough
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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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. Get your first month of Shopify for only $1 at https://shopify.com/solved Let Rocket Money help you reach your financial goals faster. Sign up for free: https://www.rocketmoney.com/solved Ready to stop listening to podcasts and actually start taking action? Join the Solved Community, a group of like-minded people who are taking small steps every day to make big changes in their lives: We also put together a free companion guide for this episode with all the takeaways, references, and tools to help you get your sh*t together once and for all. Download it here: https://solvedpodcast.com/dating Sign up for my newsletter, Your Next Breakthrough. It will help make you a less awful person: https://markmanson.net/breakthrough 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 Learn more about your ad choices. Visit megaphone.fm/adchoices