How Do I Handle Dating While In The Middle Of My Divorce?

Jan 29, 2026 by Coach Corey Wayne
Photo by iStock.com/NoSystem images

Some things to consider if you’re going through a divorce while dating.

In this video coaching newsletter I discuss an email from a viewer who’s in the middle of a divorce. He’s about to have a second date with a woman who seems to have high interest, but he’s worried about how to handle disclosing that he’s in the middle of a divorce.

My comments are in bold italics like this below in the body of his email.

This particular email is from a viewer who’s got a second date with a woman who seems to have interest, but he’s probably seen too many movies, too many TV shows that tell a guy he’s got to get all his issues out in the open, confess all his sins, confess all his fuck-ups, tell a girl everything that is unattractive about him, and somehow, magically, she’s going to fall in love with him and want to have his children.

So this guy is thinking, “When do I spring on her that I’m in the middle of a divorce? And how do I even bring it up or talk about it?” Well, the short answer is, quite frankly, it’s none of her business. This is only a second date, and if it does come up, you could just say, “Yeah, I’m divorcing” or getting divorced, and she says, “Well, why?” Just say, “Well, we just weren’t compatible. She’s a great girl, love her family. We parted on good terms, but she’s Brazilian. I’m in the States and again, we we’re not compatible, but it was a great experience. I got to see Brazil. It was awesome.”

So let’s go through his email and see what is going on.

Photo by iStock.com/tolgart

Viewer Email:

Hi Coach Corey Wayne,

A few updates on this whole situation:

So I had answered an email of his about a month or so ago when he wrote in about this, telling me what had happened, and it was pretty clear his wife was checked out and long gone. The other problem that they had was they were doing long-distance. He was in the States, she was there. Plus, he was just acting like too much of a beta male, too much unattractive behavior. So she lost interest. Plus, he also thinks that she may have really been after the green card. She wasn’t that into him. Plus, with his behavior, she was not going to fall deeply head over heels in love.

I am seeing other women. But when I say “seeing other women,” it means I’m going on a lot of first dates, around 2-3 times a week. Women have filtered themselves out for multiple reasons. Some just ghost, which I’m not too butt-hurt about. One has said she’s down for a second date, then when I text to handle logistics she hit me with, “I need more communication in early stages of dating, so I won’t be coming anymore.”

So it sounds like he’s doing a lot of online dating. I guess he didn’t jump through his butt enough and now she’s mad. Again, this is why you follow the permutations that are in the book. So women are going to get upset. Women that are boss-girl energy or too arrogant, again, especially in the dating apps, women got all the leverage. So you’re just going to have to go through a lot of these to find a good one. If you’re a social guy, it’s easy for you to meet women in person. You’re just going to have much better results with that than trying to compete in online dating. Unless, of course, you look like Brad Pitt.

Another one leading up to a first date, after logistics were set up, told me it was weird how I didn’t want to text at all. I did text her, she didn’t reply to my text, and I just didn’t chase her when she failed to reply.

Again, this is why you do this. This is all part of the vetting process. Is she serious? Does she want to meet you? Is she really interested? So she claims he didn’t want to text at all, but he texted her and she doesn’t reply. Then she blames him for not texting. What does that sound like? That sounds like a fucking fruit loop, or a girl that found somebody she liked better and just didn’t want to go out with him. Of course she blamed it on him, but again, if you’re going to do online dating, you’re just going to get a lot of that kind of flaky behavior, but if you don’t mind it, it’s another source of leads, and it gives you plenty of cannon fodder to practice on.

And so on and so forth. All this to say there are some enjoyable dates, but I’m trying not to be needy and desperate, and it looks like I’m running into a few women who are put off by the fact.

Well, what do I say? Easygoing, easy to get along with, nice to you, and flexible. These women are flexible and they weed themselves out. That’s the whole purpose of why you follow what’s in the book so you don’t waste your time, but again, if you’re going to do online dating, you’re going to encounter a lot of screwed up women. There’s catfishing going on. You got hookers and sex workers on there.

So again, you got to sort through a lot of garbage, and now you got AI coming online. I would imagine in the coming years, you’re going to have instances where guys think they’re talking to a girl and they’re just talking to an AI that’s been taught like Andrew Tate would teach an AI. So it’s just like, man, if you got a healthy social life, things are going to be so much easier to meet women in person and trying to compete in the sewer.

The other thing you got to remember, it’s like most of the people that are on the dating apps are men anyways, so why go where you’re outnumbered? Go to places. You’re going to have better results. Go to a Pilates class that has nothing but women than trying to compete against a bunch of Chad Thundercocks that won the DNA gene pool lottery and are incredibly handsome.

Photo by iStock.com/Mininyx Doodle

With Virginia, her weekend trip to Nashville went by seemingly without a hitch. I texted her this morning saying I hoped she had a good time, and telling her I’d love to see her at the restaurant we were discussing in our past date. I’m going to transcribe the messages exactly as they are below:

Me: “Hey, I hope you had fun in Nashville! Let’s get together this weekend for Italian. How about Friday, 7:00 p.m.?”

I would typically say, “Hey, I’d love to see you this weekend. What’s your schedule like?” But you can do that too. I mean, either way, you can try both ways, but it just saves texting. Instead of saying, “How about Friday at 7?” And she’s already got plans, “Oh, I can’t do it Friday,” You say, “OK well, what day are you open?” If you just opened with, “Hey, I’d love to see you this weekend. When are you free to get together? Hey, I’d love to see you this weekend. What’s your availability?” Then let her tell you, because you’re trying to get to the finish line with as few steps and as few texts as possible.

Her: “Good morning! I’m having some issues with my messages, so I only briefly saw your text this morning before it disappeared. But I would love to meet up this weekend! I’m free Saturday or Sunday evening.”

Uh, that just sounds like BS. “Oh, I didn’t see your message.” A girl who’s always on her phone didn’t see his message, or his messages just disappear because her phone’s broken because the messaging service is broken, that doesn’t make any sense. That sounds like he texted her and she waited to text him back until the next day or something, and then basically says, “Oh, your text disappeared.”

Me: “That’s OK. I’m going to try again and let’s see if it sticks. I’ve got a reservation at the Italian place we talked about earlier on Friday at 7:00 p.m.” (She hearts this message)

Her: “That sounds lovely!”

“You’re so lovely.”

Me: “Great! Do you want me to pick you up, or would you rather meet me there?”

Well, instead of giving a choice, I would say, “Hey, what’s your address? I’ll come pick you up.”

Her: “Would it be really out of your way? It looks like I’m only 11 minutes from there, but I’m not sure which direction you’d be coming.”

Me: “It’s not out of my way at all. I’m happy to pick you up, and it’d save you the Uber ride.”

Her: “Cool, then that works for me.” (I heart this message)

Me: “See you Friday.” (She hearts this message)

Well, I would have gotten her address because it doesn’t sound like he has her address.

Her: “Do you like classical music? Specifically, old Russian composers, ha? I forgot I have two tickets to the Symphony Orchestra’s performance of a selection of Tchaikovsky on Saturday evening.”

I know I butchered that name.

Me: “Yeah, I’m into classical actually. That sounds like a great way to spend Saturday. I’d love to join you.” (She hearts this message)

Photo by iStock.com/Deagreez

Her: “Ah nice! It starts at 7:30 on Saturday at the local concert hall.” (I heart this message; She sends a link)

Me: “Great! I’m looking forward to it!”

Her: “Me too! I’m glad to have the company!”

So from what I can tell, I handled myself well in the first and second dates. I was careful not to pursue. I was present and in the moment, with decent conversation, and I made sure to kiss her on both dates. I even dropped her back at her house on the second date.

OK, so he knows where she is then because he’s been there. So if you’ve already been there, just “Hey, I’ll pick you up at seven,” instead of “Would you like me to pick you up or do you want to meet there?” You want to control the controllables.

My biggest issue is I don’t know how to handle the ongoing divorce thing. If it kills the momentum completely with this woman, then fine, it is what it is.

I don’t see how it would. It’s all about how you handle it, how you answer it, and quite frankly, it’s really none of her business. If she asks you, “Are you married before?” Just say, “I’m divorced,” and if she really digs, just say, “Yeah, I was married to a girl in Brazil, but we just weren’t compatible and just waiting for things, the paperwork to be finalized,” and there’s no reason to dwell on it. You don’t have to confess your sins or tell her the whole story. It’s not going to help you. It’s not going to make you look more attractive. So whatever you say, have a positive spin on it, just like the book talks about.

There are plenty of other women out there, a bus every 15 minutes, etc. If I can move on from my wife leaving me, I can move on from a woman I haven’t even slept with yet deciding this is too much baggage for her.

Again, I wouldn’t be worrying about this at all. It’d be a non-issue. The only way it becomes an issue is if you make it an issue, and it looks like you’re clearly worried and concerned about it. So if it’s not a big deal to you, it won’t be a big deal to her. You should explain it in a way that’s just kind of very matter-of-fact with a positive spin. “Oh, what happened? Why didn’t work out?” “We just weren’t compatible. I mean, she’s great. We parted on good terms. I was on good terms with her family. They loved me, wished me well, and I wish them well. It was really nice, actually. I have plenty of friends that got divorced and it was really nasty and contentious, but that’s not us. I’m just happy to move on. Now I’m here with your cute face,” and then change the subject.

It’s just that that particular outcome would suck, and I would like to stack the deck in my favor as much as possible.

Again, she’s not your priest. You’re interested in sex and romance, so she doesn’t need to know all the details of your divorce. If you’re in a nasty custody battle, she doesn’t need to know that. As far as she’s concerned, everything’s handled. It’s going great. You’re divorcing on good terms. Then change the subject. It’s not important.

What I told her before was that I was in a two-and-a-half year relationship that recently ended. I want to break this news in a way that feels like I wasn’t lying, and that it’s 100% done with my ex and it’s only paperwork at the moment in an uncontested divorce.

Well again, what you told her was enough. You don’t need to elaborate it on any more. Just say, “Your divorce hasn’t gone through yet?” Just say, “We’re just waiting for the paperwork,” but again, I already told you what to say. It’s like you’re worried. You’re creating a mountain out of a molehill. This is really not an issue to be freaking out about.

She revealed to me that her last relationship was six years. That she wasn’t ready to move too fast, which worked out for me because I’m also not looking to jump headfirst into a full relationship.

How would you handle this?

Well, what is your job in the courtship? As the book says, it’s to create an opportunity for sex to happen, to hang out, to have fun while you’re hanging out, and when the signs are there she’s ready to be touched, ready to be kissed, ready to be seduced, to seduce her. Very simple. Create the opportunity for sex to happen.

Photo by iStock.com/Johnce

You’re not there to confess all your sins and give her all the dirty laundry about your pending divorce. It’s not important information. She doesn’t need to know it. It’s not going to help you look better or more attractive. So just tell her what she needed to know. You recently got out of a relationship, yeah you were married, but you’re just waiting for the paperwork to come through. You divorced on good terms, you’re on good terms with her family, she’s on good terms with yours, and you live happily ever after.

We have our date this Friday. I’d like to get this out in the open…

No, don’t bring it up. It’s like, dude, you think you got to show up and confess your sins? It’s ridiculous. You’ve been watching too many TV shows and too many movies that have brainwashed you. This is not important information. You want to be doing and saying things that are going to raise your attraction, which are all detailed in the book. If you’re new and you haven’t read it, it’s free to read at UnderstandingRelationships.com. Just subscribe to the email newsletter.

…So I’m not in a situation where things get sexual, she finds out, then she blows up at me and ghosts me for being a liar.

Thanks again, Coach.

Sincerely,

Bob

Again, there’s no reason for you to be freaking out about this. This is absurd. It sounds like the excuse that you gave her initially. You just got out of a relationship is enough. If she presses you on it. “Well yeah, I was married. We were getting divorced. It was long-distance. We weren’t together for very long. We just realized we weren’t compatible. You know, her family’s great. We all got along, but her and I, we’re just not compatible. I wish her the best. She’s already dating somebody else. At least I have a nice, clean divorce, not a contentious one, because everybody knows people going through divorces that are really nasty and contentious,” and then change the subject. If it’s not positive, it’s not uplifting, if it’s not going to make you look more masculine and attractive, keep it to yourself.

Again? I wouldn’t bring it up. Hang out, have fun, and hook up dude. It’s a very simple formula. She had a breakup. What she really wants to do is escape from life and have a good time with you, and hopefully beat up her pelvis and give her lots of happy finishes. That’s what you should be focusing on. Again, the divorce is like that big. It’s not even important. You’re only making it important because you’re worried about her approval. That’s not masculine.

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Published on January 29, 2026

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