Why Dating Women Going Through A Divorce Is Not Ideal

Coach Corey Wayne
17 min readMar 21, 2023
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Why dating women who are going through a divorce is not ideal, and why you should avoid them.

In this video coaching newsletter, I discuss an email from a viewer who started casually seeing a woman 4 years ago that he had known for about 10 years once she became separated from her husband. She’s in the middle of contentious divorce. She is a successful alpha female who lives in another state. For the first 2 years it was effortless. For the last 2 years she’s been hot and cold, as her divorce has gotten difficult with her ex.

She will ghost him and not respond for weeks at a time, and it’s very frustrating for him trying to arrange to get together for a date. This is a classic case of why you shouldn’t get involved with women in the middle of a nasty divorce. My comments are in bold italics like this below in the body of his email.

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I get so many emails. I’ve done countless phone sessions over the years with guys that get involved with women like this. But it’s just a good cautionary tale. He was leery at first, because he’s familiar with my work, but he was like, “Well, I’ll give her the benefit of doubt.” And things are really good for two years, but when things got really messed up is when her emotions were all over the place. And so, even though it was good for a couple of years, the last couple of years have not been very pleasant for this poor guy.

Viewer’s Email:

Hey Coach!

My name is “Bob” and I’m a long-time listener, and I’ve read all 4 of your books, multiple times. I’m really digging both volumes of your Quotes, Ruminations and Contemplations books.

Obviously, he’s talking about these beauties; I’ve got two volumes out so far, Volume I and Volume II. They’re available in Audible, Kindle, digital ebook, paperback and hardcover versions. What everyone tells me about what they like about the quotes books is that it ties the concepts in the first two books together really well. So, if you guys are so inclined, go and get yourself a copy.

I have the hard cover editions of everything and have followed along on 2x speed through Audible, which makes getting through everything multiple times a breeze!

Here’s my situation. I’m 46, a successful, semi-retired entrepreneur living my best life after a brutal and costly divorce about 10 years ago, (married young, had a kid, toxic relationship and a brutal divorce that I asked for and it cost me over $200,000 PLUS 12 years of alimony and I lost a vacation home).

Photo by iStock/AndreyPopov

Yeah, if you’ve been married for a lot of years, and especially if you build a business while you’re married, and especially if you live in a blue state, the downside financial risk and just risk in general is really super unpleasant. I was only married for a year, and I live in a free state of Florida, and we didn’t have kids or anything together. I had started my business, but she got an attorney. Everything was on good terms, and then she goes and gives triple the size of a retainer that I gave my attorney when I started.

And then, what this guy was basically doing was just writing letters to my attorney, just trying to drag things out, probably because he spent the retainer money that she gave him. That’s the one thing I noticed. A lot of those divorce attorneys, some of them are broke as a joke. And when you give them a big retainer, they don’t really like having to give any of that back. And so, what this guy was trying to do was spend every last bit of it and drag it out.

It took close to three years to actually get my divorce finalized, to get rid of the property, the house that we had together, and it just wasn’t a pleasant process. And it was extremely expensive, even though we were together one full year. So, you can imagine, especially if you live in a blue state, you’ve got kids, you’ve got businesses, you’ve got assets, you’re going to pretty much get taken to the cleaners. So, from a financial perspective, a business perspective, it’s just not a good deal for the dude.

So I highly recommend, if you are going to get married, do some kind of a civil ceremony where you have like a business agreement together. Whenever you go in a business, the right way to do it is to have a partnership agreement between the partners. It spells out all of their duties, what they owe the company, the corporation, in this case a relationship, and the consequences if one or several of the partners don’t hold up their end of the bargain. How do you disengage legally? It’s like you take care of all that stuff.

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And then, if one wants to dip, wants to retire early, or has an illness, or maybe gets hit by a bus, how do you handle their part of the equity, or their relatives that are going to inherit it, that kind of stuff. So, you can do a good job with spelling all these things out in a partnership agreement. And then you guys can get each other rings, and you can have a little ceremony with your friends, and not involving any religious people, or the state for sure. And then, you have a simple agreement and you can spell out in there.

Also, what happens if you guys split up, and you have kids and all that? It really will save you a lot of grief. Because, man, when you get the state involved in these laws and divorce courts, it’s just a bad, bad, bad way to go. So, something to consider for you guys that are determined to get married and involve the state. You know, look at this guy here — twelve years of alimony, he had a vacation home he lost, $200,000.

I had a friend of mine that married a girl, and her family is very wealthy. They had investment properties, and so he was going to give her the home that they lived in, and he was going to keep the investment properties and his office. And so, like a dummy, he just signs a quit claim deed and hands it to his wife. And then, when they’re going through the divorce process, he lost the house because he signed it over like a dumbass. And then, on on top of that, she’s like, “I want half the investment properties.”

And after it was all said and done, she basically told him, “I didn’t want you to have enough money left to where you could have another family.” In other words, she wanted to be the only one that he had kids with. And so, she smiled to his face, and lied her ass off, and had every intention of stabbing him in the back. And I’ve known her pretty well. We’ve known each other 20 years, as well. I knew his wife, and I was like, geez! I was surprised that she did that, it was disappointing.

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But, man, when emotions get involved, there’s no logic, there’s no reason, especially with a woman. They just they look at things differently. When their emotions get involved, they’re going to get really squirrely. Like I said, my buddy, he figured they had everything worked out. Just like myself and my ex-wife. We had everything agreed to, but she just turned it all over to her attorney. And unbeknownst to her, he’s writing all these letters back and forth. And obviously, every time my attorney writes him back, I get charged for each letter going back and forth. And this is going back 25 years ago, I spent thousands of dollars in his letter writing campaign.

Also, my ex-wife-to-be, her attorney could basically not have to refund any of the retainer that she had given him. But for the attorneys, the longer the conflict goes on, the more money they make. It’s in their interest to keep it going and keep it contentious. And we were divorcing on good terms. But what ended up resolving it, and I wrote about this in my book, was I ended up calling her father and told him what was going on, because he was like, “Why is this still not finished yet?” So, I told him, I was like, “Hey, man, I could use your help.” And when I told him what was going on, he thanked me for it. He hung up the phone with me, and called her attorney, and basically told him to knock it off and to get the signed separation agreement over to my attorney. And my attorney called me literally the next morning and said, “Hey, I’ve got the agreement here.” We scheduled the hearing, and then 30 days later, I was finally officially divorced.

You guys have really got to think very carefully before you get involved, because even when things seem nice, you get attorneys involved… And my buddy, he eventually left his wife, because the last three years of their marriage they weren’t having sex, and it was just a bad situation. But he thought they had everything worked out. And so, like a dummy, he just trusted that she was being honest with him and signs over his the personal residence. And the judge was like, “Hey, you signed a quit claim deed. You’ve got nothing.”

Photo by iStock/AndreyPopov

And so, he ended up losing half of his investment properties as well. All because she was vindictive about it, and was trying to punish him financially, and make it so he couldn’t afford to go and have another family with somebody else, which he ended up doing anyway. But you know, it sure would have been nice because that was probably over $1 million worth of net worth. He lit a match to $1 million. Poof! Gonzo. All because he was gullible and trusted his ex wife, who hadn’t had sex with him in over three years. But the goal is, I want you guys to learn from this stuff, especially younger guys. Learn from us older dudes that have been through it and got a few nicks and bruises here and there.

I learned that you can’t put a price on peace and happiness, and I’ve been dating some of the hottest women, but have no desire to be married ever again.

About 4 years ago, a woman I’ve known for about 10 years, and who now lives in another state, became separated from her husband. She began reaching out and pursuing me before she even filed for divorce. I was reluctant to get involved.

Well, I even talk about this in “3% Man,” why you shouldn’t get involved with these women. Because, again, women are emotional creatures, especially when there’s butthurt involved. It’s very likely that they’ll say one thing, and then somebody starts talking in their ear. It could be a friend or a relative, it could be a new boyfriend.

That was another thing. My ex wife started dating this guy, I don’t know, six, eight months after we had split up. And he was trying to be helpful, so he started creating problems, just because he was trying to get her to go after me. He thought he was being a helpful boyfriend, and it just kind of gummed up the works. So, you just never know. That’s why I said, when you get the state involved, oh god, what a nightmare.

But the connection was one of those once in a decade type ones you talk about. For 2 years it was effortless on my part, and I began to make myself too available to video chat or talk on the phone, (normally something I wouldn’t do with women I’ve dated who live in my city, but the long-distance thing threw me off).

Photo by iStock/FilippoBacci

So, his game was tight for about two years, and then he started to become an emotional tampon on the telephone. So, on top of her divorce becoming contentious, he starts becoming more of a therapist on the phone, and then spending less time in person, therefore, she lost respect for him. And once she lost respect for him, then that just exacerbates the situation when her divorce becomes difficult and contentious.

She flew out to see me multiple times and invited me to come stay with her and we rendezvoused to multiple vacation spots all over the world. She’s a successful alpha female who runs her own business, and she has the flexibility to travel regularly, just like me, (as opposed to many women I’ve dated who only get 2 weeks of vacation a year and are not available to travel).

Yeah, that’s the other thing. If you’re an entrepreneur, and you can make your schedule, and you can come and go as you please, and you’re dating a woman that has a corporate job or the type of job where she gets like 1 or 2 weeks of vacation a year, you’re like, “Hey, let’s go away for the weekend and take Friday and Monday off.” She’s like, “Oh, I’ve got to put in a request 60 to 90 days in advance to get those days off.” And it’s like, ugh. It’s nice not having to deal with that.

She’s playful, feminine, smart, matching love languages and hands down the best sex of my life. About two years ago, she went cold and completely stonewalled me after an international trip that I thought was amazing. She went from video calling me multiple times every day to sending a vague “I miss you” or “I love you” texts every few weeks. When I’d respond with variations of “Great hearing from you! I miss you too, when are you available to connect?” I would be met with silence for 3 weeks before getting another I love you text.

The other thing to keep in mind, you can’t put all of this on the girl. Because this guy, his game seemed to be tight for two years, and as he admits, he got really sloppy and started violating principles. If you’re trying to make a date and then you get ghosted for three weeks, you’re going to try one more time to make a date. And if you get the same response, then you’re going to stop bringing up getting together until she brings it up next.

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And she’s in the middle of a divorce, part of the problem is two years in, this guy is emotionally invested, he’s projecting his fantasy onto her of what he wants her to be, or who he believes her to be, and he’s ignoring the fact that she goes to him for three weeks. And then he goes right back to the same behavior — overpursuing, being too nice, too available — when he should have just looked at the situation and recognized that he made a mistake, or had made a lot of mistakes, and just kept dating other women.

I backed off completely, using your “7 Principles to Get an Ex Back,” and took note of your advice about dating women who are going through a divorce, (and hers is messy, like mine). This worked, and 8 months later she reached out and said her divorce is almost done, she doesn’t want to live her life without me, and asked if I would consider seeing her again. I probably should have made her earn me back a bit more, but things just seemed to pick up right where we left off, (except this time I didn’t make myself as available to talk or video chat and probably did 5% pursuing, if that).

Okay, so he took corrective action, which is good. So, good job on that. But he’s still involved with a woman in the middle of a divorce that’s not going well.

She flew out 3 times, and I spent most of last summer out with her, (though I got my own place for the weeks she had her kids), and we did two more trips together. The last trip, about two months ago, was great, but when we got back, it was a repeat of the stonewalling.

Maybe he was acting dopey in the trip. More than likely, also, things are really screwing with her emotions because of the divorce..

It took her 3 weeks to reach out after we got back, and she had some very loving words and even told me I’m her soulmate.

Oh, “I’m your soulmate, but I haven’t heard from you in three weeks.” Sure. You’ve got to look at the actions there. And part of the problem is this guy’s a little dopey over this girl. It’s the best sex he’s ever had in his life. And, again, he’s looking at his fantasy of who he imagines her to be and ignores the fact that she ghosted him for three weeks. I mean, that’s just rude. That’s not loving, that’s not kind.

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And this guy should have been dating other women but, again, he’s just got this girl on a pedestal. He’s being extra nice to her, and she’s not really having to do much to earn him. It seems like he’s just sitting around waiting on her to reach out to him, and that’s the only thing he’s got going on in his personal life. And that’s part of his problem. He’s doesn’t have the same level of cockiness and swagger that he had in the very beginning. Plus, he’s enabled her behavior by teaching her that it’s okay to treat him this way, and he’ll just drop what he’s doing to see her as soon as he hears from her.

I responded playfully and asked when she’s available to have a video date and was met with silence. So, obviously there’s no congruency with her words and actions.

Well, you shouldn’t be pursuing somebody when they’re trying to earn you back. You shouldn’t reach out for any reason, because you didn’t talk for a whole eight months. So, it’s obvious that, yeah, there was issues going on with the divorce, but for a woman just to disappear for eight months, that tells me that her feelings had completely gone away for the most part. And she may have been sleeping with somebody else that lived closer to her. You really don’t know, because you’re living long distance from each other.

So, I’ve gone back to no contact, only responding playfully when she reaches out and asking her availability to talk or video chat.

Again, two times in a row. And if you’re met with stonewalling or they won’t make time, you’ve got to understand –and this guy should know better at this point when he’s read all my books like this — when a woman is reaching out like that, and then you try to make dates, and then you get silence, what she’s really doing is stirring the pot and just seeing if you’re still on the line, so to speak. In other words, just seeing if you’re still interested, still on the hook. And soon as she gets that validation, poof, she’s gone. There may be another dude in the picture on her part.

I’m prepared to walk and never look back and I’ve stopped asking her availability to get together when she does reach out.

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Again, the book says no more than twice. So does “7 Principles To Get An Ex Back,” but it doesn’t seem like you followed that, because you’re trying to force her to want you more and to make more of an effort, instead of letting her come to you at her pace.

But I still respond playfully and unperturbed. My divorce took 2 years, and hers seems to be taking even longer to complete, (ex-husband trying to go after her business, parenting schedule, etc.). In the meantime, I continue to date 2 or 3 local women, but I don’t have the same chemistry or spark as what I had with her.

Well, what you’ve got to look at is that, so what? It’s like, you’re not seeing her. And what’s happening is this guy is projecting his fantasy onto her, and he’s making all kinds of excuses and rationalizations for her behavior. And plus, on top of that, he’s enabling it. It’s like, every time she finally does reach out, he’s begging her to spend time with him or video call, and then she just blows him off. And then, as soon as she does reach back out, he goes right back to overpursuing a little bit.

I feel like I know your material enough and have not repeated the same mistakes as the first go around…

But you got to understand, it taught her that you’re always going to be available and you’re always going to be waiting around. You’re always going to be willing to jump through your butt to spend time with her. You’ve given her all the leverage in the relationship. In other words, you kind of made her the leader and the man in the relationship, and you became the chick. And that’s why you’re sitting around with blue balls and your thumb up your butt.

…with the exception that I should have told her to just call me when her divorce is final.

Photo by iStock/LinaDes

What should have happened when she came back, and I discussed this in 7 Principles To Get An Ex Back,” but it doesn’t look like you listened, is that she has to do 100% of the calling, texting and pursuing from there on out. And it seems like once you started spending time together again, that you kind of went back to pursuing, as you said, 5%.

But as it talks about in “7 Principles To Get An Ex Back,” if she’s trying to earn another chance with you, she’s got to make the effort. She messed it up, she’s the one that ghosted you. She’s the one who disappeared for eight months, and then she’s the one that asked you for another chance. But when she asked for another chance, it doesn’t mean you go back to pursuing her again, because that’s part of what got you rejected the first time around. That’s why when you’ve gotten dumped, you’ve gotten blown off, as it says in “7 Principles To Get An Ex Back,” she’s got to do 100% of the pursuing. And you didn’t follow that, because you were in la-la land. You’re too dopey over this girl.

My plan is to continue dating, but I’m half tempted to just ignore any future messages from her due to the disrespect in ignoring my question about getting together. I would love to hear your thoughts. Fruit loop?


Well, again, you keep asking her to get together when you shouldn’t be doing that. You’re not following what my book teaches. So, I’d be nice, I’d be playful, but unless she brings up getting together, I wouldn’t mention it at all. And again, it says right in “7 Principles To Get An Ex Back,” when you ask a girl to get together and she won’t make the plans, you don’t ask. You ask twice max, two times in a row. Then after that, she’s got to bring it up. And unless she brings up getting together, you’re not going to mention it.

Photo by iStock/fizkes

I wouldn’t be doing any FaceTime calls or any of that stuff. And I would honestly be looking at this like putting a fork in it. But part of the problem is that you’ve got a woman that’s going through a nasty divorce. And on top of that, you’ve continued to overpursue, even after she blew you off and disrespected you, I don’t know how many times. It’s like, your behavior didn’t change until she basically ghosted you, and that’s when you finally recognized that you were overpursuing. And even then, when she started coming back, you went right back to pursuing. And that’s just the opposite of what I teach.

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 and book a coaching session with yours truly.



Coach Corey Wayne

Life & Peak Performance Coach. I Teach Self-Reliance. Subscribe To My Newsletter To Read My eBooks “3% Man” & “Mastering Yourself” Free: http://bit.ly/CCWeBooks