Wealthy Way

This Is Why Men Are Losing at Dating (Even With Money & Looks)

5 snips
Jan 1, 2026
Jack Selby, a content creator and podcaster known for The Iced Coffee Hour, dives into the complexities of modern dating. He discusses how dating apps create a false sense of security while also fostering rejection anxiety. The duo highlights the disparity in attention men receive on these platforms, which often leads to frustration. They also explore how dopamine-driven hookup culture undermines real intimacy, and provide actionable advice for overcoming fear and hesitation in dating. The key takeaway? Be direct and don't overthink your approach!
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INSIGHT

Most Relationships Start Online

  • Online dating has become the default way couples meet, replacing most in-person first meetings.
  • Ryan Pineda notes a study showing about 80% of relationships now start online.
ANECDOTE

Filming Dates To Dull Rejection

  • Jack Selby describes planning to ask many women on dates and film it to reduce nervousness and create content.
  • He admits fear of rejection drives his idea to make the attempts into videos so rejections feel less painful.
INSIGHT

Apps Soften Rejection, Fuel Instant Gratification

  • Dating apps add a perceived safety layer that softens rejection and feeds instant-gratification behaviors.
  • Jack argues apps create addictive dopamine loops and often favor hookups over long-term intimacy.
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