Should I Settle Down With One Woman Or Continue Being A Free Agent?

How to know when to settle down & when to continue being a free agent.

In this video coaching newsletter I discuss an email from a viewer who left his 10 year marriage with 3 kids 3 years ago because he says he realized he settled. He’s been having a blast being single and having a rotation of women. However, now he wonders if he should be settling down with any of the several women he’s dated since his divorce that would have been great girlfriends. My comments are in bold italics like this below in the body of his email.

Hi, I’m Coach Corey Wayne and this is my Video Coaching Newsletter. And the topic of today’s Members Only Newsletter is, “Should I Settle Down With One Woman Or Continue Being A Free Agent?”.

So this particular email is from a viewer who’s been following me for ten plus years. And he said about three years ago he ended his ten year marriage. He and his ex-wife have three kids together, and it was like a non-contested divorce. So they parted on really good terms.

He says he realized that he’s settled and obviously he’s gun shy about doing that again. But he also wonders if he’s maybe been a little too harsh and too judgmental because in the last few years he’s dated a lot of really cool, attractive women and he says would make good girlfriends and good relationship material.

But now he’s wondering if, you know, he could have had a few good relationships with some of them. And so he’s like, “How do you know if you should settle down or not or be a free agent or whatever?”

Viewer Email:

Hey Coach,

I’m a 40 year old straight white male, drug and disease free, non-smoker here. Ha, ha.

What is DD? I don’t know what DDF stands for. It’s probably drugs. Something maybe he doesn’t drink, doesn’t drink, doesn’t do drugs or something. (Drug and disease free.) I don’t know, maybe you guys can point it out in the comments.

I’ll try to keep it short – long time follower here, 10 plus years. I’ve studied all the books, including the Quotes, Ruminations & Contemplations – Volume I, Quotes, Ruminations & Contemplations – Volume II.

Which there are actually two of those by the way. So this is the first Quotes, Ruminations & Contemplations book. It’s been out for a few years. Every time I do this, people are like, “I didn’t know you had a quotes book. I didn’t know you had a second book.”

And this is the second Quotes, Ruminations & Contemplations. These are the hardcover versions. They’re available on audible, and they’re available on paperback, hardcover, digital, iTunes just for your reading pleasure.

The Way of the Superior Man, etc. reading all of them at least 5 times over the years. I still go back from time to time and listen. Three years ago, I walked away from a 10 plus year marriage with 3 kids uncontested. Thanks for the advice on that.

Because even though I got married and divorced when I was young, we were only together for a year, we had a pretty good friendship. Afterwards, she dated a really good buddy of mine from high school for several years. And it’s like I looked at her as like family, you know, I loved her. She was a great wife and I had no complaints. Changed my life.

I’d probably be dead in a ditch somewhere if it hadn’t been for her to come along and love me unconditionally like she did. So, you know, she saved my life in a lot of ways. And she was a good woman, even though it didn’t feel right and I didn’t feel like I wanted to be married to her, I did it because she was such a good person. But I wasn’t ready to do it. I wasn’t ready to settle down and have a family and all that stuff.

I did it because everybody talked me into it. I mean, obviously I go into detail and 3% Man about that, but I have nothing but gratitude. And if you really, truly love somebody and care for them, you want them to be happy, even if it’s not with you. And so a lot of times over the years, I’ve done phone sessions with guys that are in the middle of a divorce and they’re trying not to give all their money and their net worth to their attorneys and to keep as much of it for them, for each other and their children, instead of giving it all to the attorneys.

And the more you let the attorneys handle things, their job and mission is to keep the conflict going so they can continue to get paid. Every time they write a letter, 4 or 500 bucks. Here you go. You know, they’re writing notes to each other’s attorneys every week, and it’s just sending you thousands of dollars of bills every month.

And usually the guy most times ends up paying for it anyway. So, if you guys can negotiate things together in an equitable manner that you both agree to, that’s a win win deal. It’s like you’re going to save a lot of money in the process. Because otherwise you come out of it financially fleeced and hating each other and it’s not good for your kids. So you’ve got to think about that.

Here and now I’ve been dating for probably a year and a half, having been with about 10 women in that time. I’ve got a rotation, but I’m thinking more about my long-term goals. I noticed I’m a lot less willing to compromise.

Well, as you get older, you get to the point where you really don’t give a fuck. It’s like you don’t care what other people think. And you realize most of the time when you’re younger and you’re worried about what other people think, they were thinking about other things anyways besides you.

That was a big issue with my last relationship I settled, so I’m making sure not to do that this time.

Well, you got to trust your gut and your intuition. And as awesome as my wife was, it didn’t feel right. I didn’t want to get married, but I felt trapped, and everybody told me, “I needed to go do it. I just had cold feet”, but it didn’t feel right. And I did it anyways because I trusted other people’s opinion over my own. And ever since then, that was one of the biggest lessons that came out of it.

One of the things Wayne Dyer said, “When you trust in yourself, you’re trusting in the same wisdom that created you.” And so your intuition really; when I’ve not listened to it, bad things have happened or suboptimal things have happened. Let’s put it that way. When I do listen to it, things always work out great in the end.

I start to question though, where do you draw the line and decide you’re in? Obviously nobody is going to be perfect and check every box, right?

Well it will feel right. It’s because you want kids and a family with her and you want to spend your life with her. And you know, being with one person that you want to build something together, a family unit, you and her. Maybe you add some kids. Maybe you’ve already had kids. You’re an empty nester, and maybe you’re going to have dogs and cats or whatever, or parrots or something. Or you just want to enjoy each other’s kids and grandkids, whatever it happens to be, depending on what stage you are in life.

I’ve got kids in high school that are following me, trying to get a date for prom, and dudes that are 70, 75 years old that just lost the love of their life that they were with when they were 15. So I’ve got everything in between. My job as a Coach is to help you get what you want. And at the end of the day, do you want to build something with this person, or would you want to see what else is out there?

And when you find the right person, you know, when you really want to be in a relationship with them, you know, your intuition is screaming from the inside of you. It feels right. And so just the fact that he’s writing this tells me that as awesome as these ten women have been, he shouldn’t have been with any of them long term. He did the right thing. There’s nothing wrong. You didn’t do anything wrong.

You’ve always ever done what you were meant to do anyways. What happened, happened, and it couldn’t have happened any other way. You know, as guys we get to a point where we’re comfortable and we’re stable and we want a stable relationship. You know, some of us like to be dads. Sometimes we get to be stepdads. Sometimes we get to have our own kids. Sometimes we have a mixture of some of their kids, some of our own kids together.

You know, it doesn’t matter. The idea is that you want to build something together. You and her, you’re content. She’s content. You don’t want anybody else. You don’t want to be single anymore. You just want to be with her because you jive so well. So when you light up on the inside and you feel it in your heart and your soul, then you’ll know your feelings are your truth anyways.

A couple of these girls, we really clicked, but it wasn’t completely there for me.

Well, at the end of the day, remember “Woman Of Your Dreams.” “Winning The Heart Of The Woman Of Your Dreams”. Not how to attract somebody mediocre. That doesn’t really do it for you. You’ll know there’s a big difference.

I would notice this early on, 1 to 2 months, and end the relationship immediately to spare wasting anyone’s time which I think is the right thing to do. Obviously, I’m a great catch. I’m constantly working on myself, I make outstanding money, and keep myself in good physical shape, I’m great with kids. These girls are devastated, and I feel bad, but we’ve got to be honest.

Yes, you have to, because the worst thing in the world is to be dishonest with yourself and the other person, and then have to look them in the eyes and break their heart because you married them or decide to be in a relationship and you didn’t really want to. That’s, you know, like I said, the worst thing in the world, one of the worst top five things I’ve ever had to deal with in my life was sitting in bed and telling my wife that I didn’t want to stay married to her anymore.

I felt horrible, but afterwards I felt so relieved. And so from that point forward, I really started speaking from my heart and my core and what felt right for me. And it just became a lifelong pursuit to live that way. And never again would I doubt myself in that way and go back on what I felt was right.

If, for example, the sex was lacking in experience, or she just wasn’t at the same stage of life as I am, no kids experience, versus having kids. When do we decide some things can be worked on versus accepting nothing but the best?

Well, think about your closest friends. Your best friend, even. You just jive. It just works. You like hanging out with them. They like hanging out with you. You love each other. Hopefully, you’ve been in each other’s lives a long time. You know, it’s like one of my best friends I ever had came over yesterday because I always exercise equipment showing.

And he and his oldest basically put it together just because he wanted to do it and come over and put stuff together. It was like, this is awesome. So we’ve got a full gym on the fourth and the first floor, got all brand new gym equipment coming. So I’m pretty excited about that. So everybody gets to use it, including yours truly.

I guess that comes down to each individual and their own tolerances, but I feel like at this point I’m being extremely selective. 

And you should be. Again, how often do you meet a new best friend? Once a decade, maybe? Every 15 years. It’s like great people they’re good to you, good for you, good for your soul. They almost never come along.

Which, for the record, I have no problem being single, I’ll probably be single the rest of my life. But I do wonder if I’ll pass up on some potentially great relationships in that time. And some of these girls I really would like to be friends with, our minds work together really well, but I don’t think they would go for that, so I just let it go.

Yep. Because again, when you find the right girl, it’s like you’re not going to want to hang out with these other chicks and your girl’s not going to want you hanging out with these other chicks either. That’s the bottom line. Unless, you know, you’ve got multiple girlfriends or multiple wives. I’ve got clients like that too. So you do you boo boo. Whatever makes you happy.

Maybe these are all test by the universe preparing me for something bigger.

Well, I found that to be the case.

I know it’s still real early in the game and time will tell, but just thinking out loud for now.

Thanks,

Bob

Dude. Keep moving. Keep circulating. Keep your practice squad going. Remember, you’re adding to your practice squad. You’re dropping girls from your practice squad. You’re keeping girls on your practice squad. And if a new prospect comes along, she comes to your practice squad and she goes quickly from your practice squad your active roster.

It’s like, well, then you’re going to probably drop your whole entire practice squad and focus on the main girl on your active roster. And you’ll know. It’ll feel right. Just like when you meet the people that became closest to you, you just know there’s something special about that person, about that relationship that’s beyond the physical. You’ll know in your heart and your soul.

Again, your feelings are your truth and trust that, like Steve Jobs said, “You’ve got to trust your heart, your curiosity, and your intuition. Because they somehow already know what you want to become.” And again, like I said earlier, because you want to build something together with that person and nobody else.

So, if you’ve got a question or a challenge and you’d like to get my help, go to UnderstandingRelationships.com, click the Products tab at the top of your screen on any page, and book a coaching session with yours truly. Until next time, I will talk to you soon.