This Is Why Men Are Losing at Dating (Even With Money & Looks)
Wealthy Way
Ryan Pineda
4.9 • 2.2K Ratings
🗓️ 1 January 2026
⏱️ 12 minutes
🧾️ Download transcript
Summary
Ryan Pineda and Jack Selby explore the challenges modern men face with dating, fear of rejection, and overthinking, ultimately revealing how content creation, dating apps, and social norms shape romantic confidence today.
Watch the full interview: https://youtu.be/-jkPOKftb5c
Connect with Jack:
https://www.instagram.com/jlsselby/
https://www.instagram.com/icedcoffeehour/
https://www.youtube.com/@jlsselby
https://www.youtube.com/@TheIcedCoffeeHour
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CHAPTERS:
0:00 - The Death of Old-School Dating
1:00 - Rejection, Fear, and Dating App Addiction
3:30 - The Illusion of Options and Real Intimacy
7:00 - Real Advice: How to Actually Ask Someone Out
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About Ryan Pineda:
Ryan Pineda has been in the real estate industry since 2010 and has invested in over $100,000,000 of real estate. He has completed over 700 flips and wholesales, and he owns over 650 rental units. As an entrepreneur, he has founded seven different businesses that have generated 7-8 figures of revenue.
Ryan has amassed over 2 million followers on social media and has generated over 1 billion views online. Starting as a minor league baseball player making less than $2,000 a month, Ryan is now worth over $100 million. He shares his experiences in building wealth and believes that anyone can change their life with real estate investing.
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Transcript
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| 0:00.0 | So I met my wife in college. |
| 0:02.5 | And I think that when I got married was kind of like the end of like, oh, we meet people in person. |
| 0:10.2 | That's how you first meet. |
| 0:11.8 | Like, dude, online dating and stuff was super weird back then. |
| 0:14.8 | Meeting somebody online without having met before in person, like just DMing them out of the blue. |
| 0:20.0 | That was weird. |
| 0:21.8 | Now it's like, I forgot the study. That was weird. Now it's like, |
| 0:30.1 | I forgot the study I saw, but I think it's like 80% of relationships start online. Eventually, I'd like to do something where I go up and I like ask 100 girls on a date or something like that, |
| 0:35.4 | because I feel like it will make me less nervous if I film it, oddly enough. And could post it and I feel like that would be really good content and hopefully people could watch my now we're ringing this back to making it a YouTube video but but it will make me less nervous because I'll be like hey at least if I get rejected I have a funny video which you know and I also think that do you think you fear rejection then like is that why you're yeah |
| 0:56.2 | you're not dating you're afraid of rejection I don't think that's why I'm not dating but I fear rejection |
| 1:00.3 | for sure I think everybody fears rejection especially single guys like it's just kind of a thing and if |
| 1:04.6 | you don't you're like in the top 0.1% of guys well I understand that nobody wants to get rejected. |
| 1:11.5 | Yeah. |
| 1:11.6 | I understand that. |
| 1:12.9 | But for most people who are basically what you're describing, the fear of rejection keeps |
| 1:19.2 | them from ever playing the game. |
| 1:21.9 | Yeah. |
| 1:22.8 | So do you think that you don't play the game out of the fear? |
| 1:26.1 | Well, that's why I think dating apps are so |
| 1:28.2 | popular now is because it kind of adds a level of safety between you and getting rejected. |
| 1:34.4 | Because it doesn't feel like real rejection. And, you know, you don't see a bunch of rejection. |
| 1:39.5 | No, it doesn't. Like when you swipe and then you just don't ever see their face ever again because |
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