My Dates Keep Failing. Why Would Anyone Pay Me for Dating Advice?

My Dates Keep Failing. Why Would Anyone Pay Me for Dating Advice?

After watching some of my dating videos, you might be surprised to learn that I actually offer one-on-one calls, Zoom calls, and dating coaching right here on my website. And one person messaged me about that. Bobby messaged me and said he's new to dating, so why should he buy my coaching if I keep talking about my failed dates, my mistakes, my wasted time, and wasted money? He said, "I don't have time or money to waste."

And I'm not saying you should buy my dating coaching. What I am doing is sharing my real, raw, authentic, lived experience here. And that's what almost no one else is doing.

What Almost Every Other Dating Coach Is Selling

Almost everyone else has systems that are set up to generate profits for them. I've watched a number of other dating creators, at least a hundred, and they mostly have these business systems that position these scarce, limited spaces. Then they sell. They qualify you and sell you on thousands and thousands of dollars. And they sell based on authority. They sell the idea that "I have all the answers, and I'm going to tell you what to do."

I've paid for one of these myself. I paid $75 for one of Bobby Rio's programs, and it was disappointing. Even though I like his videos, his program was just more of the same stuff. I don't remember finding anything useful in it at all. And what's even worse is what most people are selling. It's based on, at least as a man, using your head to date. It's about playing games with women. It's about setting up and understanding this whole game. And yes, Bobby Rio's book, The Invisible Game, was helpful. But when's the last time Bobby Rio actually went out on a date? He is working with other people.

I'm in the Arena Right Now

What's unique is that I'm doing this myself now. I'm in the middle of this now. It's like this: if you wanted to learn how to play basketball, you could certainly go to a coach. Or you might want to go to a player who's actually playing right now themselves, someone who can show you, "This is how I practice. This is how I turn my practice into a performance during the game. This is how I handle the rest of my life." I'm in the dating game, in the arena, right now myself. And that makes me unusual among dating coaches, because almost none of the other players in the arena are dating. None of the other dating coaches are transparent about what they're actually doing in their own dating life right now.

And I can tell you, it's very easy to build yourself up as an authority by saying things that sound smart, by convincing people you know stuff, by talking about all these clients you may or may not actually have, and in some cases even by stealing other people's material — taking it from another coach, calling it your own, and then selling it as a system. What I offer is radical transparency. I tell you exactly what I'm doing on my dates and what I'm learning.

The Scarcity Mindset Hiding in That Question

The first thing I would look at in Bobby's message is that it feels like scarcity to me. If you have true abundance, you do have time and money to waste. I have time. I can afford to just play video games. I can just do nothing, or create content. And I have money to waste. I've blown tens of thousands of dollars on dating, and a lot of it has not gotten the result of me having a great relationship with someone else. I have a great relationship with myself, and at the same time I have so much abundance — I have more money and time, and I can keep investing in dating.

One of the biggest things I've observed in myself is the scarcity mindset. And the scarcity mindset is so sneaky. With a scarcity mindset, you'll often be put in the exact right position and then rationalize why you shouldn't go forward. And I love that I'm out here sharing the realest, rawest dating content — realer and rawer than what anybody else is doing.

How I Make Myself Available

This is where I offer my coaching. You can just grab a quick ten-minute call with me if I'm online. If I'm not, you can schedule a thirty-minute call. That is cheaper and more accessible than anybody else is. Some of these other people offering these programs — if they had a simple way where I could just go in, schedule a call, and ask them some questions, I would do that. I offer that. If you want an hour and a half, you can book calls in a row and talk for an hour and a half. What I'm doing that I'm proud of is I make it easy to just show up and talk to me.

Most of the other people I see doing dating videos have what look to me like exploitive systems, where they are intentionally not available at all to help you. They don't tell you how much anything is going to cost you. They try to get you sucked in and committed, and then you're dumping a whole bunch of money into these programs. I personally don't like being told what to do. I don't want somebody trying to force me into their rigid system. I just want somebody I can have a real conversation with.

I'm lucky that I have several people who are like dating coaches to me, and they're free. If you can get somebody like that for you, that's the ideal option. I have a guy who has been a psychologist for decades. He'll sit on the phone with me and talk to me for an hour about dating. He will help me see what I can learn and what I can change. He'll help validate me and affirm me.

Open Heart Instead of Head Games

What's important with dating is not just approaching it with your head and having a rigid system. What I'm proud of is that I'm looking at dynamics like: am I approaching dating with an open heart? Of all the guys I've watched talk about dating, almost none of them talk about having an open heart and putting some genuine feelings of love out toward the woman on a date. It's all head games. It's all tricks. It's all playing this invisible game. How about you just show up and love the person in front of you, say thank you, and pay attention to them? What I'm intending to do is show up on a date with an open heart and an open mind toward a woman. That's the opposite of what a lot of people are teaching — to show up with checklists, to show up with games and routines ready to go, to show up and mess with her in a way that tries to spark attraction. Some of that stuff can work really well to generate hookups, but it doesn't generally work well to make a heartfelt, long-lasting connection.

I have had a fifteen-year, mostly amazing relationship with a beautiful woman. I have a couple of kids, and I had a kind divorce from that. I don't see any of these other dating coaches transparently offering any of that. I'm here in a way that is available and supportive — if you don't need me, or if you'd rather get sucked into one of these guys' programs and pay a whole bunch of money to them, that's your call.

The $1,200 I Paid a Real-Life Dating Coach

I personally have paid $1,200 for an in-person, real-life dating coach. I got out to real in-person events with her. She even set me up on a date with one of her friends. Now, none of the events got me a woman to date, and the date with her friend, whom I already knew, did not go anywhere — but the date was fun. The events helped break me out of my comfort zone. She took some pictures for me, which I still use for my business; I've got them as profile pictures. We had a fun time going out to the pier.

The only person I've paid serious money to for dating coaching is a friend I knew in person, and it was well worth it. We hung out. We had fun. We had great conversations. She got me in the habit of going to events to meet women in person, so now I know where to go: run clubs, free yoga, comedy events. We did a comedy event together, and it was fun. That money supported her and her business. So yes, I've paid $1,200 for a dating coach — in person, in real life, with a woman.

Everything I've Tried This Year

At the same time, there's nothing better than my own lived experience with dating. I'm doing this right now. I didn't date ten years ago and then just coach a bunch of people. There's a big difference between "I'm in the arena now" and "I did this before." I remember I used to do dating courses and videos about dating when I was married. What I can say is my stuff now is much better, because I'm actually in the game.

Unlike basketball, which is very similar from decade to decade even as the players evolve, dating changes fast. I like playing basketball — I've taken my daughter to play, and I can hit two or three three-pointers in a minute, about one three-pointer every thirty seconds, which is pretty good for a dude who was born in '84. Yet the game of basketball tends to stay pretty similar. The dating game evolves pretty quickly, and I'm in it right now, trying all kinds of different strategies.

Where I can help support you is if you're not sure what to do. I've tried matchmaking. I've tried dating apps. I've tried going to events in person. I've tried cold approach and warm approach. I've tried getting fixed up by friends. I've tried just praying and hoping. I've tried not asking women out. I've tried going out with an open heart and attracting women. I've tried running mental games. I've tried texting a lot, and I've tried hardly texting at all. I've tried so many different things, and I've done all of this in the last year. I've gone out with a woman who was trying to get a job. I've gone out with a woman who was 23, a woman who was 57, and everywhere in between. And I ask other people their stories. Because of that, I have a lot of real lived experience from this year.

What's beautiful about working with me is that I'm not going to tell you what to do. If you hate being told what to do, I can provide support. I may suggest, "Maybe you should read this book," or, "I tried this, and you might think about it." What I find is that you need to have people you can talk to about dating — people who have more experience than you, or who have been doing this more recently or for longer than you. My friend has been married and divorced three times and has kids. Any story I have, he's got five similar stories. It just helps to talk with someone who has more life experience than you, even if it's just a little more, or even if it's the same amount of life experience and it's a little different.

For example, some strategies I have on the back burner: if I don't have a relationship in the next few months, I'm going to save up some money and go overseas, try a few different countries, and see if I can meet a woman overseas.

That will add value to what I'm doing. I have four more dates left on my matchmaking. I'm thinking about trying dating apps again. I'm going to speed dating and a mixer. I'm in the middle of this. That's why my dating channel has taken off — because I'm not out here telling you all what to do.

Why Generic Dating Advice Backfires

What most of these people get wrong in their dating videos is giving all this generic advice. The problem with dating is that you're often looking for an outlier — someone who's not going to respond to you like everybody else. A lot of the things you can do to deal with the masses will actually push an outlier away. For example, I can run game on a woman, get her interested in me, and play these games to get her attracted to me. But is that going to do anything more than generate a hookup? Because if I want a real heartfelt connection with a woman, I need to really feel her, and she needs to really feel me.

I've gone on a couple of dates with beautiful, wealthy women who were very intelligent, and I just ran game on them. They liked me after the first date. But the messed-up thing was I could hardly like them, because I was focused on staying in my head, running game, and doing what these other people had suggested. I couldn't feel a connection to them. I remember the woman I was out with two weeks ago — so beautiful, so smart, so compatible in so many ways, not compatible in some ways. I remember feeling sad. I thought, I can't feel this woman. She's here. She's next to me. She's talking. She's sharing. And I'm analyzing her, reading her logically, processing her — but my heart is closed and I don't feel anything.

It's hard to text a woman when I don't feel anything. When I feel something for her, I can easily be flirty and fun and just text her, and it feels good. But with the woman from a couple of weeks ago, it was agonizing to text her, because every time I had to run through all these routines in my mind to figure out what to say.

Comfortable With the Complexity

There's so much advice out there that might work in certain situations and will also destroy other situations. What I am comfortable with in dating is the complexity. Some of these creators said one thing a year ago and are saying a different thing today. Some of them tell you to act like a top guy, take your time with text messages, and play all these games. The women I've had in my life — I didn't play any stupid games with them. That taking-four-hours-to-respond stuff seems to mostly turn women off, though there are perhaps some kinds of women it turns on. That's what's tough about dating: your situation is unique, and there's so much complexity. I'm comfortable with the complexity, and I break things down ultra simple.

Look — show up with an open heart. Are you able to go on a date with a woman and feel her? Do you feel excited? Do you feel love for her? Do you feel respect for her? Do you feel attraction to her? How do you feel with the woman when you're on a date with her? And if she said something really disturbing, would you feel hurt and sad and ready to leave? That will show you're open-hearted. How do you feel when you're texting her? Do you feel excited? It's fun texting her when it's naturally easy to flirt and send messages that turn women on, because I'm feeling that way myself.

What I Actually Offer

So I'm not saying anyone should pay me for dating advice. I'm saying I'm available — if you want someone who's in the game now, not someone who played the game twenty years ago and has been coaching the whole time since then, not someone just telling you what to do without being transparent about what they're doing. I'm a holistic person. I look beautiful because of how I eat, how I think, the sleep I get, the way I parent my children, and the kind divorce I had with my ex-wife. A lot of dating, to me, is cleaning up the mess in the rest of your life. One reason dating is a challenge for me is that the rest of my life, by comparison, is easy. I take care of myself. Parenting my kids is easy. I get along with most people, and I have friends, family, and people I can talk to for free about all this stuff. I have a family member who just coached me on online dating for free for about an hour on the phone.

And I'm just here if you need me — if you need someone to listen to you, to support you, and to give you a point of view that might be helpful, I'm here for you. If you want support, I can offer that. If you want guaranteed results and certainty, I don't provide that. And these other people are not providing that either. They're the same as me in that way — the difference is I'm out here hustling, and they're out here tricking you.

Some of these dudes selling dating coaching are not the kind of guys I'd be friends with or trust in real life. These are guys where I wouldn't want my daughter to go out with a man acting like that, talking like that, and treating women with that kind of a mindset — a guy who's proud of how many women he's hooked up with. Ew.

So if you want what I have, here's what I have: no matter how much this doesn't go well, I talk about it. I share it no matter how embarrassing it is — you can see every one of those stories on my Dating playlist. And I keep trying. I don't quit. Everything I do is a learning opportunity, and then I try to teach others. I think that's very admirable.

I'm here if you want the help. And if you want something else, go get it.

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