Spotting & Avoiding Women Who Are Difficult & Structured

How to spot & avoid women who are difficult & structured.

In this video coaching newsletter I discuss an email from a viewer who kept dating a woman who was displaying signs of being difficult and structured. A few months in she started complaining about him and what she didn’t like in and out of the bedroom. Then she got sick and he became her caretaker and the sex stopped. Eventually he left & realizes it was a mistake to stay. 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 Newsletter is going to be, “Spotting & Avoiding Women Who Are Difficult & Structured”.

Well, this particular email is from a guy who, despite the signs that she was difficult and structured, he continued dating her. And then a few months in, she started complaining about him, especially in the bedroom. She didn’t like how he was doing things, but she couldn’t really explain things in a way that made any sense. And no matter what he did, she was not satisfied with it.

So and then she got sick, I guess she got cancer. And then he became her caretaker. As soon as that happened, the sex stopped, and eventually he left. And he realized it was a mistake to stay. And he was like, “man, was she structured from the beginning? Should I have dipped out early on?” The obvious answer is yes. This is why you don’t date structured women. Because they’re quite frankly a pain in the butt.

They’re not easygoing. They’re not easy to get along with. They’re difficult. They’re argumentative, often disrespectful. And they expect you to jump through a bunch of hoops that are usually ridiculous. And even when you do it, you’re not doing it right, which as you’ll see here.

Viewer Email:

Hey Coach,

Thanks again for all the work you do. Your material has been a big part of helping me get clarity in my dating life. This is my second letter — the first one you covered was, “Should I Reach Out To Her Or Wait To Hear From Her?” September 25, 2024. Since then, I’ve read your book several times, watched countless videos, and worked to internalize your principles. I’ve dated a lot, not chasing sex, but looking for a woman who’s truly worthy of my long-term affection.

Well, easygoing, easy to get along with. And she’s got to be nice to you. Nice and respectful. Not constantly breaking your balls, trying to make you question yourself or doubt yourself, or constantly insulting you. Or like in this case, constantly saying you’re doing things wrong, but yet she can’t explain exactly what you’re doing wrong. There’s some people who go through, as Wayne Dyer said, “some people go through life looking for occasions to be offended.” And just some people are like that. Some women are like that. Even when things are good because of how they were raised, they just start looking for reasons to bitch and complain just because that’s the way they are. You want a woman that will make your dick hard, not your life.

In mid-November 2025, I met a woman who seemed like a great catch. She was 49, an attorney who excelled in her career, kept her life in order, stayed fit, and carried herself with class. By all appearances, she looked like a competent woman.

Maybe she acted like a man. It’s tough dating female attorneys. They can be very difficult and argumentative just because that’s the way they are. They argue all day for a living. I remember I’ve told this story. I had a good friend of mine. He was dating a woman who was an attorney. This is probably 16, 18 years ago. And this, this friend of mine made a lot of money when he was younger in the tech industry, and he’s basically 25 plus years, has been just living off his interest and investing. He’s been an equity investor. I had him on my podcast, The Corey Wayne and Bob Podcast.

And so he was dating this woman who was an attorney, and then she was bringing up them getting married. And with a straight face she expected him just to agree to this. She says, “well, I want a prenuptial agreement that basically says, if you cheat on me, I get all your money.” I was like, what? I remember when he told me I was like, what? You’ve been dating this woman for a year and a half. You and everything you went through to earn this wealth. And not only to earn it, but to keep it and to grow it since you’ve been out of the industry.

And it’s like, she just expects you to go, “oh, yeah, that’s a good idea. If I ever cheat, I’ll just give you all my money and basically be broke and homeless.” It’s like what? Well, needless to say, within a matter of days, he pulled the rip cord and he was out of there. But to her, that seemed like a normal request. And she could be difficult and argumentative because, again, she was an attorney. That’s what she did for a living, was argue with people. Argue and negotiate.

On our first date, the conversation flowed and there was attraction, but when I went for the kiss, she gave me the cheek.

What does the book say? She’s structured and not interested. Either way, on to the next.

She was still warm and friendly, but looking back I now see that hesitation as an early sign she might be structured.

Again. It’s in the book. It’s in the book. We don’t date structured women because again, they’re difficult and they’re a pain in the butt. They’re not easygoing, they’re not easy to get along with. They’ve always got to set of rules. They’re never satisfied. There’s always some other kind of protocol they want you to satisfy. Again, this woman’s an attorney, so she argues for a living. She’s used to being difficult for a living.

That’s how you get the other side to cave and negotiate and give up more than they normally would have, by just basically being a pain in the ass and dragging things out and getting to the point where they’re just like, I just want this to go away. So that’s everything she does. And she’s 49, he said, so this is her whole world. This is her life. This is what she does. So you can imagine trying to take that kind of armor off and then come home and be a sweet, feminine, girly girl that’ll let you lead and submit to you. Probably not going to happen.

Within the first few dates we had sex, but it wasn’t very good. The connection just wasn’t there. At first it slowly improved, but then she started complaining about how I touched her.

Yeah, that’s a drag. If you’ve been with a woman and then she’s like, “Oh. My ex used to touch me like that. Or he used to do this to me. And I don’t like that. I prefer this position. Here, do this, do that.” That’s just a pain in the ass. You want a woman that submits and just lets you have your way with her, not like fucking bossing you around like a mechanic. Or tighten that bolt. Loosen up that fan belt.

Her feedback was so vague it was impossible to figure out what she wanted.

She wanted to complain and argue because that’s what she does. That’s just normal to her.

It felt like she had one script in her mind for how intimacy was supposed to look, and if I didn’t follow it, she grew frustrated.

It’s like, yeah, I’ve come across a couple of women who are like that. They want you to, “oh, it’s got to be in a certain way. Sex has to be this way. You have to pull down. Push this way.” It’s like. What? Come on.

That’s when I started to wonder if this was what you describe as a structured woman.

Well, it would have been helpful if you read the book. It’s free to read in the Members Area on the Website.

After that, I stopped exploring new ways to please her and just reached for the Hitachi, which turned intimacy into a chore.

Reach for the Hitachi? I don’t know what that is. He says. The Hitachi. Is that a TV remote? Somebody help me in the comments! I don’t know what the hell he’s talking about. Probably a joke that just sailed over my head, but okay.

A couple of months later, she was diagnosed with breast cancer. I supported her through the first two rounds of chemo, and during that time our sex life stopped completely. After the first round, I noticed her pulling back. By the second round, she went cold and distant, and it was clear she was having serious issues with the relationship.

Yeah, I don’t think he had actually read the book when he was dating her. Maybe he thumbed through it. I’m just surprised that he was, even now he’s scratching his head going, “is she structured?”

Meanwhile, I had slipped into more of a caretaker role than a lover. I lost interest in sex with her.

Well, it doesn’t sound like sex was very good.

Didn’t see things changing, recognized the negative impact this dynamic was having, and ended the relationship last week.

Well, at least she pulled the ripcord finally.

Looking back, it seems clear why things unraveled. Her structured nature in general turned me off. I just wasn’t excited to be with her sexually. On top of that, I slipped into more of a caretaker role during her treatments, which likely turned both of us off and killed attraction.

From her side, the lack of intimacy clearly pushed her to pull away.

Well, it wasn’t such a bad thing that you were taking care of her when she was sick. A good boyfriend would do that regardless. But you’re dating an attorney who’s a structured pain in the ass, and no matter what you did, she’s not satisfied with it. And she couldn’t give you directions on what to fix. And it sounds like she’s just a miserable, unhappy person. And no matter what you were going to do or say, she’s going to be displeased with it. Because, again, as Wayne Dyer used to say, “some people just go through life looking for reasons or occasions to be offended.” “Oh, don’t touch me like that. Oh, you’re reminding me of an ex. Oh, I don’t like it when you do that.” Like what?

So I’ve got two questions for you.

Number one, was I seeing signs of a structured woman?

Yeah.

Number two, how do you support a partner through a health crisis without slipping into the caretaker role and killing attraction?

Number three, any insight would be greatly appreciated. And thank you again for all the work you do. Your material has truly made a big difference in my life.

Well, you’ve still got a date and court her, and you’ve got to have fun with her. Most importantly, hang out, have fun. Hook up. Right? Remember the formula. The have fun part, you were hanging out and you were hooking up, but it doesn’t really sound like even from the beginning, it was a lot of fun to be with her. And you just ignored that. Probably because she was pretty and you liked her, but you ignored the fact she was a structured, difficult pain in the ass. You’re not going to have an easy and effortless relationship with her. You want a woman that’s got a bubbly, happy personality. Happy to see you, happy to be with you.

It’s kind of like dogs. Dogs are always just happy to be around you. They don’t need much. As long as they’re with you, they’re happy. Cats on the other hand, tend to be a little fickle and difficult, but not all of them. But this one in particular is just cranky. And no matter what you would have done, she probably would have been complaining about it. Because again, that’s what she does for a living is she complains and she makes people’s lives difficult in order to extract as much money and wealth from the other side as possible. That’s what attorneys do. They just wear you out with letters back and forth.

They drag it out over many months, so you get tired of paying your attorney’s bills, and you just want to settle and make them go away. So their whole lives are about being a difficult, structured pain in the ass, if you will. Because there’s a method to the madness. And she clearly cannot take that work negotiation, armor off and act like a fun, playful girl. She was putting on a good act at first, but as soon as you got to know each other and she felt comfortable and felt like she had you, then she just basically behaved the way she always was.

Again, when you go to kiss a girl and it sure looks like she’s interested, but yet she gives you the cheek and gives you something like, “Oh, I only kiss after the fourth date”, or some ridiculous thing like that, don’t date structured women. I say it all the time, but, you know, I still get emails from guys like this who don’t really listen. And, you know, just think all the time in the emotional and mental energy wasted on this girl and how frustrating it is to date somebody like this. Because, like, no matter what, you don’t feel successful at making her happy. And as men, we want to feel like we’re successful. If our girl is happy, hey, we’re the shit. If she’s miserable and unhappy, well, we suck. We take it that way.

And when you’re with somebody for a long enough period of time. And no matter what you do, they’re never happy. They’re never satisfied. They’re always complaining and getting upset with you. It’s just eventually you check out and you give up because you’re like, “no matter what I do, she’s not going to be happy. So fuck it.” In the future when you spot this behavior, get out. Unless you’re a glutton for punishment like this guy was.

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.

And if you haven’t already signed up for our Exclusive Premium Members Only Content in the video description of this video, there are links to join on YouTube or Spotify or our Website UnderstandingRelationships.com just click the “plans” tab when you get there. And you can sign up for a seven day free trial to check out what content you get for your money. And if you choose an annual plan, you can get a 25% discount at the end of the seven day free trial. So go to UnderstandingRelationships.com, click the “plans” tab, sign up for a premium free trial. And until next time, I will talk to you soon.