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Why Dating Women With Unresolved Divorces & Relationships Is Risky & Painful

Dec 19, 2025 by Coach Corey Wayne
Photo by iStock.com/laflor

Some things to consider if you’re going to date women with unresolved divorces & relationships.

In this video coaching newsletter I discuss an email from a viewer who was dating a woman with an unresolved divorce. She still accepted gifts from and spent time with her ex-husband to be. He told her he was uncomfortable with this and she said moving in together would fix it. He declined because of her inappropriate behavior & unresolved divorce. She dumped him because he wouldn’t commit. He’s in no contact and wonders how a healthy relationship could develop if she comes back. 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, “Why Dating Women With Unresolved Divorces & Relationships Is Risky & Painful”.

So this particular email and again I go and I discuss this in 3% Man. If you’re going to date women, ideally you should be dating women who are completely through the divorce. It’s done. They’re divorced. In other words, they didn’t just file yesterday and they’re still living with their ex and their kids under the same roof. Or they’re still talking to the ex or living with the ex. But, you know, she’s dating and sleeping with other people.

He’s living in the house trying to get her back. I wouldn’t get involved with those. Because if you start dating somebody that’s fresh out of a breakup, you’re going to get hot and cold behavior. And anytime something goes sideways with the divorce, because especially if there’s kids involved, it’s usually very contentious and their emotions are going to be all over the ice. So one week you’ll have a great weekend together and the next week she wants space or she’s taking time to return your calls or texts.

She gets a little distant and it’s just up and down like a fucking Yo-Yo. And that’s not a lot of fun. I want you to have a good experience with the ladies and dating women. If you’re gonna date women who are in the middle of a divorce, that’s unresolved. Or like an unresolved relationship. You gotta understand it’s got to be messy and you’re the one doing them a favor. And so it’s important to set and enforce healthy boundaries and moderate expectations.

If you’re going to date a woman that lives with her ex-husband and he’s trying to get her back and the kids live at the house, she lives at the house, and she’s just basically sneaking around and dating you and won’t tell anybody that you guys are dating. Like, you’ve been dating six months and you’re supposedly boyfriend and girlfriend. But in reality, if she’s still living under the same roof and she’s going on vacations with her ex-husband and the kids because they’re doing it for the children.

Photo by iStock.com/PeopleImages

Then really, what you are is you’re a married woman’s side piece. In other words, you know the running joke about a guy having to deal with his wife’s boyfriend? It’s like you’re that guy. You’re the side piece. And if you’re a guy that’s wanting a healthy, happy, normal relationship, it’s not going to happen when she’s still living with the ex or still is in the middle of a contentious divorce, just because the behavior is going to be all over the ice. And you’ll see this. You know, this guy’s had not a very pleasant experience.

And so on top of that, the ex-husband in this case was buying her jewelry and stuff. And then she’s wearing it. He’s like, “We’re in a relationship. And yet your ex-husband is buying you jewelry, probably because he wants you back.” And her suggestion is, “Well, we should live together. That’ll solve all these problems. You won’t be worried about me because we’ll be living under the same roof.” He’s like, “I don’t really want to live with you because quite frankly, you’re somebody else’s wife.

I don’t know when or if you’re even actually going to get divorced. And plus, I don’t like how close you guys and your interactions are. Again, why would I want to be boyfriend and girlfriend and live with a woman who’s still allowing her ex husband to buy her jewelry and things because he’s trying to get her back, or he still views her as his wife?” No self-respecting man is going to want to deal with that. And so again, if you’re going to date somebody like that, it really should be more of like a booty call.

In other words, you offer her exclusivity if she’s gotten all these things out of the way first. If not, if she’s going to continue to live with the ex, then I would practice safe sex. I would treat her like an occasional booty call. I would let her do 100% of the reaching out. And you can make dates, but if you want a long term relationship, I’d be dating other women and looking for somebody who’s single and ready to mingle, not being some married woman’s sidepiece.

Because again, you can waste a lot of time and then you have to deal with a breakup when it doesn’t work out, especially if she doesn’t resolve the issues. And so when she suggested he move in, he’s like, “I don’t feel comfortable with all the stuff that’s going on. So unless that changes, no, I’m not ready to live with you.” And so after that, she dumped him saying, “Well, I dumped you because you wouldn’t commit to me.”

Photo by iStock.com/nd3000

So who wants to commit to a married woman? I mean, that’s kind of silly. “Oh, hey, this is my girlfriend. But, you know, she is married and has a husband and lives with him and their kids. But, you know, we’re in a great relationship, mom and dad.” And your parents would be like, “What?”

Viewer Email:

Hi Corey,

I recently came across your videos while dealing with a difficult relationship situation and felt they really resonated with me. I was in a relationship with a woman I cared deeply about. However, when we met, she was still legally married, and that created ongoing trust issues.

Yeah, especially if there’s no space between her and the husband, especially if they’re living together. I’ve seen guys in these situations over the years that I’ve coached, that have sent in emails that are dating women exactly like this. They live under the same roof with the husband and the kids, and they’re doing family trips. And yet they supposedly buy a house together with the woman who’s still legally married to somebody else. They spend all the money, they make all the payments, and they just put her on the deed and give her half the house, basically when she’s not really contributing anything.

And then they get the house and then she goes back to the husband. And so now they got a house to be together. But yet she decided to give the marriage another chance. And now you got a house that she picked out that you’re on the hook for. Or they buy her a $300,000 car. Or just, you know, insane things that I’ve seen over the last 20 years doing this that guys that don’t know any better do.

There were also challenges around her social environment, frequent partying.

So she’s constantly acting like she’s single.

Photo by iStock.com/monkeybusinessimages

Once she met her husband and he gave her a necklace, and certain boundaries I struggled with for example, she continued wearing jewelry from her husband despite me expressing that it hurt my trust.

Yeah again, if he’s buying her jewelry, he’s not doing that because he’s just wanting to be a good ex-husband. Most ex-husbands don’t buy jewelry for their ex wives. They just don’t. They do that when they’re trying to keep their wives, and they don’t want them to become an ex-wife. And so, in other words, you’re dating a woman who’s basically, like, monkey branching to see if she can find something better. And acts like she got a hall pass.

Over the last six months, she pushed strongly for us to live together. I wanted commitment too, but because of unresolved trust issues, lack of clarity around her divorce, and instability in the relationship, I didn’t feel safe taking that step yet.

Yeah, think about it. You move in together, and yet she’s still spending the night under her husband’s roof. And so you’re laying in bed in an apartment or a condo or a house that you got for the two of you. And yet she’s still living with the husband. You know, you’re gonna be laying in bed at night going, “What is she doing? Why doesn’t she want to stay here? We got this house to live together, and now she’s still living there.” Again, that’s what happens when you’re the side piece.

She believed moving in together would fix everything, but I felt it would put all the risk on my side without a stable foundation.

Yeah, exactly. Your Spidey Sense was tingling. And the good news is, you listened. So good job there.

Eventually, she ended the relationship, saying I wasn’t serious enough.

I was like, well, she’s not serious enough about getting divorced because she’s still married.

Photo by iStock.com/Lyudinka

This was painful, as I genuinely loved her and invested a lot emotionally. She said it was the best sex it was and will miss it. I’ve now gone into no contact and wished her well. My question is, beyond no contact, what should my focus be if there’s ever a chance of a healthy reconnection in the future? Is the goal simply to fully let go, work on myself, and move forward even if that means dating others and building a life independently?

Thank you for your content and for taking the time to read this.

Kind regards,

Bob

Um, dude. Newsflash for you, you’re fucking single. She broke up with you. You don’t have a girlfriend. You were fucking somebody else’s wife. That’s what was going on here. And more than likely, she probably went back to him or has given the marriage another chance. Because she’s still living there. She’s not living with you. She’s living with him. So women vote with their feet. If they’re with you, it means they voted for you. And unfortunately for you, she is living. Or fortunately, she’s living with the ex-husband still. So we have to assume that they’re probably still hooking up and she’s giving him another chance.

So at the end of the day, quite frankly, you did the right thing because she’s not single and available. She’s married to somebody else. I mean, think how ridiculous it sounds to tell all your friends and your family. “Oh, this is my girlfriend, but she still lives with her husband and hasn’t even initiated divorce yet.” So if she reaches back out as the book says, your job really is to create an opportunity for sex to happen. Hang out, have fun, hook up. If you really want to continue screwing some other guy’s wife, well, that’s on you.

I would let her do 100% of the reaching out. You’d invite her over to make dinner, hang out, have fun, hook up. I would treat her like a booty call. I wouldn’t take her out on dates. And if she complains, I just say, “Look, you live with your husband, and you haven’t moved your divorce along at all since I met you. And on top of that, I’m going to continue dating other people. You can date who you want, but I just look at what we had was I was just your side piece. And I’m not going to be sexually exclusive with a woman who lives with her husband.

Photo by iStock.com/nd3000

And whose husband, quite frankly, is actively trying to get her back. Because he’s buying you shit. He’s buying you jewelry. Ex husbands don’t buy jewelry for their ex wives. They buy jewelry for the wives that they’re trying to keep, and I’m not going to get in the middle of that. But if you’re going to tell me that you’re moving your divorce along, we can be friends with benefits. We could be fuck buddies, sex playmates. But you’ve got to understand, I’m going to be dating and sleeping with other women. And when I find somebody I really click with, I’m going to get serious with her and I’m not going to be able to see you anymore.

So there’s a time limit on this. So if you want to lock me down and you really want something exclusive, then you’re going to have to leave your husband. And no, I’m not going to move in with you as a condition for you leaving your husband. You’re going to have to leave your husband because you don’t want to be married to him anymore. Get your own place and get your own life and get stable again. If you don’t want to do that, then we can be fuck buddies until I find somebody to have a relationship with.” That’s what I would do if I were you.

But I would not consider this woman a candidate for, because you don’t really know anything. She could just totally be in her marriage, and all her friends and family think that she’s still with her husband, and meanwhile, she’s just carrying on an extramarital affair with you and blowing sunshine up your ass, making you think it’s a real relationship. And the real reason she’d want to be sexually exclusive with you is just so you’re not sleeping with other women, and potentially, especially if you’re raw dogging it.

Give her some kind of funky gift that she ends up giving to her husband. Because, again, if she’s still living with him, that’s who she voted for. So we have to assume if she’s living under his roof and accepting his gifts, that they’re probably still sleeping together and you’re just one of the dudes she’s sleeping with, she might have 2 or 3 other guys like you on the side that she was dating. You really don’t know what you don’t know. So exclusivity should be something that a woman earns because she comes to the table with characteristics, goals, and values that align with that.

Photo by iStock.com/Jacob Wackerhausen

And in this case, it just looks like you’re dating, or you’ve been hooking up with a woman who’s having an extramarital affair with you. And she ended the affair. You know, again, what I’ve seen when guys do this, they go and they rent a place. Usually what happens is they get a place together. She has a key and everything, but she’s not on the lease. And she’ll say, “Oh, well, I can’t be on the lease or anything because I’m in the middle of a divorce.” And so the guy pays for a place for the two of them. And occasionally she comes and stays over, but doesn’t stay the night.

And now the guy’s on the hook for a bigger place than he wanted. Because he thought he was going to be living with her. That’s what I’ve seen happen in these cases when they’re not dunces with the husband. And she doesn’t look like she’s dunces with him. So she can be a booty call. She can be part of your rotation or your practice squad. But until she’s completely done with her divorce, I wouldn’t agree to be exclusive with a woman that lives with her husband. That’s just crazy.

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.

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Published on December 19, 2025

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