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Dating Coaching

Dating Coaching

1 month, 4 hours of Zoom calls, and text messaging support between calls for creating your best love life, most attractive self, and maximizing the opportunities you have to meet someone amazing.

Who this is for

This is for you if you're not sure what to do next in dating and you want someone to talk to who is in it right now. I'm 42, I was with my ex-wife for fifteen years before a kind divorce, I'm a single dad of two in St. Petersburg, Florida, and I've been sober since 2014. I've been dating since my divorce and I've made plenty of mistakes in public. If you're a man or a woman dating after divorce, especially with kids, a lot of this will be relatable. If you're sober and dating without a drink to lean on, I live that too. And if the advice online keeps contradicting itself, I'm comfortable with the complexity, and I break things down ultra simple.

It's also for people who hate being told what to do. I don't like it either, and I'm not going to force you into a rigid system. I'm going to listen, tell you what I've tried, and give you a point of view that might be helpful.

What happens in the month

You get four hours with me on Zoom spread across one month, and between those calls you can text me. On the calls I want to hear what you've actually been doing: where you're meeting people, what your profile says, what your messages look like, how your dates have gone, and how you feel while all of it is happening. Then I share what I've done in the same spot and what came of it. I may say, "Maybe you should read this book," or, "I tried this, and you might think about it." What I won't do is hand you a script.

A lot of the time we'll be looking at the questions I ask myself. Are you showing up with an open heart? Do you feel excited, do you feel respect for the person in front of you, do you feel attraction, or are you analyzing them and running routines in your head? How do you feel when you're texting them? Those answers show you what's really going on faster than any checklist.

Why me, when my own dates keep failing

Someone messaged me asking why he should buy coaching from a guy who keeps talking about his failed dates, wasted time, and wasted money. Fair question. Here's my answer. If you wanted to learn basketball, you could go to a coach, or you could go to a player who is on the court right now and can show you how he practices and how he handles the rest of his life. I'm in the dating game, in the arena, right now. Almost none of the other dating coaches are, and none of them are transparent about their own dating life. What I offer is radical transparency: I tell you exactly what I'm doing on my dates and what I'm learning, no matter how embarrassing it is.

Tiger Woods has a golf coach who is not as good as him. The coach is there to help him be at the top of his game. I pay for coaching myself. I paid $1,200 for a month-long program with an in-person dating coach, and it was well worth it. She got me out to real events, audited my profile, took the pictures I still use, and sat me down with a circle of women at her house to talk about dating. Altogether I've spent tens of thousands of dollars on dating, between matchmaking, apps, coaching, and everything else I've tried, and I've been out with more than twenty different women since my divorce. I've tried matchmaking, apps, in-person events, getting fixed up by friends, texting a lot, hardly texting at all, and going out with an open heart. That's lived experience from this year, not a decade ago.

And I'm not teaching tricks. Most of what gets sold to men is head games meant to spark attraction. Some of that can generate hookups, but it doesn't generally make a heartfelt, lasting connection. I've run game on beautiful, intelligent women and felt nothing myself because my heart was closed. That's not what I want for you.

What people usually bring

  • Profiles and apps. I've spent over a thousand dollars on dating apps and deleted them three or four times because they sabotaged my confidence. When I was on Hinge, I rebuilt my profile to be rigorously honest, with a video at the top so a woman could look me up before we met. We can go through yours the same way. For women who just want dates from the apps, the easiest thing is to have me go through the apps with you and set the dates up, so you only decide in person.
  • Messaging and texting. A lot of my second dates didn't happen because I wasn't putting in effort over the phone. Effort is attractive, and when the other person isn't putting much in, that's your cue to back off.
  • Mindset. Scarcity is sneaky. It puts you in exactly the right position and then rationalizes why you shouldn't go forward. I've caught it in myself, landed on "I am the prize," and stopped chasing. I'll give everything I've got, but I want mutual enthusiasm instead of convincing someone.
  • Dating after divorce, and dating sober. Dating after my divorce has been one of the hardest things I've done since I got sober. It showed me every way I had gotten sloppy in my personal life. If you're coming out of a long relationship, you're in an entirely different dating environment than the one you left.
  • The rest of your life. A lot of dating, to me, is cleaning up the mess in the rest of your life. How I eat, sleep, think, and parent is why I look and feel the way I do. We'll talk about that too.

What you leave with

I don't provide guaranteed results or certainty, and nobody else does either. What I can give you is clarity. I believe clarity is kindness. By the end of the month you'll have an honest read on your own dating life from someone who is living his, the lessons I paid for and learned the hard way, and the habit of talking it through with someone instead of bottling it up. If you don't have someone like that, this is a month of having one.

How the texting support works

The calls are where we go deep. The texting is for everything that happens in between, because that's where dating actually gets decided: the message you can't figure out how to send, the date that just ended, the day you want to delete the apps and quit. Text me what's going on and I'll reply myself with what I see and what I'd try. Having someone to talk to while it's happening is the part most people never get.

Questions you might have

Do you guarantee results? No. I offer support, a point of view, and my real experience. If you want certainty, I don't provide that, and I don't believe anyone honestly can.

Is this for men or women? Both. The help men need is often different from the help women need, and I'm available for either.

Are you going to tell me what to do? No. I'll tell you what I've tried and what I'd think about. You decide.

Do you teach pickup lines, games, or routines? No. Show up with an open heart, pay attention to the person in front of you, and say thank you. That's the opposite of what most people teach, and it's what I'm practicing myself.

Does it matter that you're sober? I've been sober since 2014, so if sobriety is part of your dating life, I can talk about it from experience. If it isn't, that's fine.

How is this different from one call? One call is one conversation. This is a month of calls plus texting while your dating life is actually happening.

If you want this, add it to the cart above.