Am I Dating A Red Flag Factory?

How to know if you’re dating someone with too many red flags.

In this video coaching newsletter I discuss an email from a viewer who’s been dating a woman who’s the opposite of easy going and easy to get along with. She’s moody and gets easily upset and gives him a hard time when her unreasonable expectations aren’t met. He says it’s exhausting. He seems like he’s always walking on eggshells and wonders if she has too many red flags.

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

Well, if you have to ask…

So this particular email is from a viewer who it looks like it’s pretty obvious he’s dating a woman who is the opposite of easy-going and easy to get along with. She’s moody, she gets easily upset, she takes things the wrong way, and she gives him a hard time when her unreasonable expectations aren’t met, which usually she hasn’t informed him of, and he’s like, “It’s exhausting.” He’s walking on eggshells and he wonders if she’s just got too many red flags.

I see this all the time. If you’re going to get into a long-term relationship, it’s got to be with a girl who’s easy-going and easy to get along with. Somebody like this, I mean, he spotted this behavior right from the get-go, but he kept dating her anyways, and now he’s been seeing her for a while and it’s just things don’t get any better. Everything’s just a catastrophe.

Viewer Email:

Hi Coach,

Hope you’re doing well. A while back you answered one of my emails on the members-only content about a girl I was seeing. Your advice worked, but ultimately I ended things because she couldn’t handle the emotional conflict between us having sex and wanting to wait until marriage due to her upbringing and past trauma, so I decided instead of the back and forth I wanted to move on to someone who was more aligned with my values. 

Just kind of seems like he went from one difficult girl to another one.

Not long after, I started dating another woman. Ironically, we’d actually met a couple years earlier when she had a boyfriend. Then in September of 2025 she pursued me at an event, got my number, and we started talking. It’s also worth noting that she broke up with her ex in August, so I was letting her do all the pursuing since her emotions were still raw.

This is exactly the right course of action, because you date enough, you’re going to come across girls that are coming out of a relationship and things are going well with you and her, but the ex is not completely out of the picture yet. So in those cases, you really got to let the woman do most of the pursuing, if not all of it, as quickly as possible, because pursuing a woman in that scenario where the other ex is still in the background and it’s not completely over, especially when he’s trying to get her back, any mistakes you make will drive her into his arms. That’s why it’s better to let her come to you at her pace. She’ll do the same thing with the other guy, and usually he’ll flail around and actually chase her into your arms. So a reconciliation ideally won’t ever happen with them, and you’ll live happily ever after with her, hopefully.

She did mention she’d been over it for months though, and had even cut off sex with him for a month before breaking things off. Anyway, I made definite plans and took her roller skating. We had an amazing time. Honestly, it was probably the best first date I’ve ever been on. The chemistry was effortless. The next morning she texted me first and was clearly pursuing. We set another date for the following Friday. Monday, she texted me first wishing me a good day. I replied and told her I loved seeing her name pop up on my phone and wished her a good day too. Then Friday arrived. I showed up to the date. She didn’t.

So keep in mind he made a date with this girl, had a good first date, makes a second date, and then she just doesn’t even show up.

After waiting about 10 minutes, I texted asking where she was. She replied that because I hadn’t texted her for three days, she thought I wasn’t interested anymore and didn’t want to go.

That’s not normal behavior. You’ve already been on a date with this girl. You make plans. She accepts. You go and show up, “Oh well, you haven’t texted me, so I’m just not going to show up.” That’s cuckoo. This is why you apply what’s in the book, so you can spot the girls that are cuckoo and do things like this. This shouldn’t be a green light like, “Yeah, let’s get another one of those.” You’ve got to pay attention to these things.

I immediately thought, “A normal healthy woman with a good self-esteem would respect that plans were made and show up because she expects her date to show up.”

Well, if she’s raised right and her father teaches her to keep her word, she’s going to do that. If she comes from a broken home or hates her dad, well you can kind of get this flaky behavior.

“And if she’s questioning it she’d just reach out to confirm, not just flake.”

Correct. “Hey, are we still on?” Very simple. It just shows that she’s not very cultured.

Coach, we’d only been on one date and she was already acting this way.

I know, this is why I say easy-going, easy to get along with. That’s what you’re supposed to be after. You don’t see this kind of behavior and go, “Oh, I’m going to give her another chance. This is great!”

We talked on the phone and she eventually came, but she spent part of the date explaining that I needed to text her more and that I should confirm dates beforehand. I told her that when I make plans, I show up. Unless something changes, confirmation is already built into the fact that we made plans. I also explained that I’m much more of an in-person guy than a texter. At the time I brushed it off. Looking back, I think it was the first sign of a bigger issue.

It’s like, yeah, you just can’t go, “Oh, this will be fine. ” he’s showing you that she’s kind of nutty. So I have a dock behind my place, and so my next door neighbor has a boat that’s sinking basically, and they’ve pumped it out several times and it was sinking. So I’m assuming the dude’s showed back up to try to pump it out, and obviously the dogs freak out about that, so I apologize. That’s the only reason that they would continue to be barking like that.

The issue wasn’t really texting. The issue seemed to be that she needed constant reassurance. The next night we slept together. Probably the freakiest girl in bed that I’ve met. 

Well, there you go. She’s a little cuckoo and she’s great in bed. That’s the thing with crazy girls. They’re amazing in bed, but they’re crazy.

A few days later she went out of town. At the time I was still dating multiple women and wasn’t heavily invested yet. She called me twice while I was out with friends. I missed the calls and called back later, but it went straight to voicemail. Months later in January 2026 we ran into each other and she told me she had blocked me because she thought I was ghosting her.

Jesus. Why would you want to fucking deal with that?

Fast forward to March of 2026. We reconnect and begin dating seriously.

Seriously?

That’s when I started noticing a pattern. Anytime something didn’t go exactly how she wanted, she seemed to interpret it as evidence that I didn’t care enough.

Then, of course, she goes and does something like that, passive aggressive behavior. “I’m gonna punish you! I’m gonna get back at you,” that kind of shit.

One example was scheduling. One day we had plans for 8:30. She got called back into work and asked if we could move it to nine. No problem because it was a legitimate excuse. At 9:00, after I’d already arrived, she asked if we could make it 9:30. At that point I simply said let’s do another day because it seemed like her schedule was packed and I’d rather spend quality time together when neither of us is rushing around. The next time we hung out she told me she felt like I didn’t care about her.

Ah, this is so tiring.

Her reasoning was that if I really cared, I would’ve waited for her that night. That confused me because I wasn’t rejecting her. I wasn’t upset. I wasn’t withdrawing. I was simply saying the timing wasn’t working that day.

Well, yeah. She keeps pushing it back and you’re fucking sitting there and she’s like, “Oh, how about a half hour later?” That’s just rude. It’s OK to waste his time, but her? Oh, no!

Yet somehow it became a conversation about proving my feelings.

So this is like when a woman is insecure and no amount of reassurance that you care is enough. That’s somebody that didn’t get enough hugs and I love you’s from mom and dad. It’s very tiring. They’re very needy.

This happened often. Another example happened recently. I temporarily didn’t have access to my car one day. A friend had offered to let me use his vehicle and said he’d leave me the keys. Unfortunately he accidentally fell asleep after driving all day and never left them.

Well that’s unfortunate.

Instead of waking up an exhausted friend who had been on the road all day, I told her I’d be running late because he had fallen asleep with the keys, but I’d walk to her, a 15-minute walk away. She became upset and told me I cared more about him than I cared about her and that I should’ve just woken him up. I was simply trying to be considerate of someone who was exhausted. But from her perspective it seemed like the issue wasn’t the situation itself. The issue was that I wasn’t putting her wants above everything else.

Yeah, it’s like things are going along good and she decides it’s something you did as a slight against her, and there’s going to be hell to pay. It’s like, why would you want to deal with that? Easy-going, easy to get along with.

Another incident bothered me even more. I was dealing with some stressful work-related issues and had become a little more distant than usual for a couple days. She noticed and reached out asking if I was busy that night. I reassured her that I wouldn’t be able to hang that night, but my distance wasn’t about her. I told her I was just dealing with some things and that I’d see her soon. What stood out to me was that she never asked what was wrong. She never asked if I was okay. She never asked what I was dealing with. Instead, the conversation immediately became about how blindsided she felt and how she starts feeling like she’s forcing things with me when I get distant. The crazy thing is, I literally just didn’t text her at all that day. One day, Corey, and she started spiraling again.

Dude, I say it constantly. Easy-going, easy to get along with, and she’s nice to you. Does that sound like a woman who’s easy-going, easy to get along with, and who’s nice to you? No. Should have never got this far, dude.

The entire conversation then completely shifted away from what I was dealing with and became about how my stress was making her feel.

That just kind of sounds like a narcissist. Everything’s always about them.

That was probably the moment where I really started questioning things. Sometimes it feels like she cares about my emotions only when they’re affecting her. She’s only warm and affectionate when I’m giving her adequate attention, if she feels like something’s off she immediately goes cold and withdraws even if nothing’s wrong.

Yeah. So you’ll set her off and then you’re just like, “I haven’t heard from her in a couple of days. What’s going on?” And she’ll just be mad stewing. Then you call her up after a week. “Hey, what’s going on? Are you OK? Haven’t heard from you.” Then you find out that she’s mad or pissed. “I’m mad. I need a few days to get over it.”

I had a girlfriend that was like that once. I couldn’t do it, man. It’s like, things would be going great, and then all of a sudden something would upset her and she wouldn’t want to talk to me. I mean like, I literally would call her, try to figure out what’s going on. She’d hang up on me and then just ignore me for like three days. Then three or four days go by, she’d call me up and want to talk like nothing ever happened. I was like, “Well, what was that all about?” “I don’t want to talk about it,” and I just got sick of it. That’s just immature. It’s not normal behavior, and you shouldn’t put up with it either.

On top of all this, she’s frequently moody.

Yep. Been there, done that, got the t-shirt.

I already know you’re probably smiling and hearing, “Easy-going and easy to get along with” in your head.

Yeah, it’s like I say it for a reason, man.

She comes from a broken home.

Well, there you have it.

Was raised by a single mother from Africa, openly hates her father, and has told me she used to hate all men before she started dating me.

OK. It’s like, all I can do is tell you what the characteristics are and the kind of women that you should consider for long-term relationships, but you haven’t been listening.

I genuinely have compassion for that. But sometimes it feels like I’m paying interest on emotional debt that I didn’t create. Some days she’s affectionate, warm, and great to be around. Other days I feel like I’m walking through a minefield trying to figure out what set her off. She’s called me ignorant for asking harmless questions about her culture.

Like, where’s the upside? The woman is supposed to bring joy into your life. She’s supposed to make your dick hard, not your life, and she sure seems to excel at making your life difficult.

I’ve heard that she has yelled at co-workers. I’m naturally playful and sarcastic, but sometimes jokes that most people would laugh at will upset her.

Yep. I had the same issue with the girl I was talking about earlier. I’m always joking around and teasing people. I would tease her, and almost 99% of the time, she took the shit personally. I would be like, “I’m just joking.” It’s like, “No, you’re not.” So she wouldn’t believe me when I would tell her. Again, she grew up without a father as well, so there’s that.

And she’ll go quiet for periods at a time. I don’t let it affect me but it’s just very off putting. The last thing I’ve noticed is that she often seems to test me instead of simply telling me what she wants.

Recently we were at an event together. She was visibly moody and distant the entire night. I chose ahead of time once I recognized this that I was gonna have fun regardless of her behavior and mood. 

Well, you should always decide ahead of time that, “I’m going to have fun tonight, no matter what.”

At one point she asked why I was sitting so far away. I honestly hadn’t even realized I was. I told her to come sit next to me. She told me no and said I should scoot closer to her. 

OK, so it’s like a dick measuring contest here. It’s like being in a relationship with a dude. You’ve got boss girl energy.

Eventually she came closer to me, but it left me scratching my head. If she wanted affection, why not simply come get affection?

Dude, I say it all the time. You’re dating a girl from a broken home and trying to have a normal relationship. I told you, it doesn’t fucking work, but you know, there’s always somebody that wants to go, “This one’s the exception, Coach. I can fix her.” It’s like, she’s not normal. That’s why she behaves this way. She hates men. So she hates men, she’s automatically gonna assume that you’re a dickhead for whatever it is you did or didn’t do. “You’re a dickhead. It’s your fault.” That’s her attitude. She presupposes that.

There’s even times when she’ll say she’s more affectionate than me, and asked me why I’m not touching her. I’ve told her multiple times that if she wants to touch me, hug me, kiss me, hold my hand, or cuddle up next to me, she doesn’t need permission. I love when she does. Instead, it often feels like she’s waiting to see whether I’ll do it first so she can measure how much I care. The same thing happens with scheduling. If she tells me she doesn’t know when she’ll be available, she expects me to keep my evening open and wait around until she decides. When I explained that I think both people’s time should be respected and that I’d rather make definite plans, she rolled her eyes and told me every other guy before me waited around for her. I said, “That’s why you’re not with them anymore” with a smirk. 

Coach, the more I think about it, the more all of these situations seem connected.

It’s a girl from a broken home, dude. I mean again, it’s like, you shouldn’t be this far down the road with her and be shocked that it’s turning out like this, but it does make for a good email because there will be other guys who’ll be listening to this going, “Holy shit, Batman! That’s fucked up!” No, thank you. Check, please. Then they’ll start dating a girl and start showing the same red flags, and they’ll do the smart thing and go, “That’s not easy-going.” I remember what the hell that chick put that guy through.

Whether it’s texting, scheduling, affection, conflict, or everyday inconveniences, everything eventually circles back to her needing reassurance, and not caring about anything else except how she feels. I know you mention women don’t care about how you feel, only how they feel about you, but I’ve been with women who are much easier going and don’t treat me this way.

Well again, you’re dating a girl from a broken home. You’re like, “Captain Save-A-Hoe to the rescue!”

It often feels like my role is to constantly prove that I care.

Yeah, dad didn’t do a good job. This is what happens.

The problem is that no amount of proving ever seems to be enough.

It’s like, yep.

A new reason for why I don’t care enough always pops up, and I feel like this is the start of something that could become super toxic down the line. It’s only been three months…

Again, after that performance for the first date, I would have not gone out on a second date. A girl that’s just basically you have one good date and then the next date, she’s not going to show up because she decided she’s upset that you hadn’t texted her, so she’s just going to stand you up on purpose. Like that’s a good thing to do. Again, dad didn’t do a good job. That should have been all she wrote, bro, but you’re like, “Oh Coach, you don’t understand. She’s really hot and the sex is amazing.”

…But I’m already feeling it. I know what it’s like to date a healthy woman with a good self esteem and the difference is night and day.

Yep.

Of course the sex with my current girl is crazy good…

There’s the rub.

…But it’s not enough to keep me around long-term if this behavior continues. 

Dude, this is the way she is.

I care about her. I’m loyal. We’ve built a lot together.

That’s built in quicksand.

But lately I’m emotionally exhausted because I never know which version of her I’m going to get. One joke. One schedule change. One misunderstanding. One busy week. And suddenly we’re having another conversation about whether I care enough. Am I dealing with a woman who is simply insecure and needs time to heal, or am I looking at deeper character issues that are unlikely to change?

Thanks, Coach.

Bob

Character is destiny, dude. I say this constantly in my videos. I’m surprised that you wrote this long, it was a well written email, a lot of detail, and you’re scratching your head going, “Gee, why is it not easy to have a relationship with this girl?” It’s like, she came from a broken home, hates her father. Girls that love their dads are great girlfriends. They make great wives. Women that hate their fathers, they’re fuck buddies, friends with benefits, sex playmates. That’s it.

So if it was me, I’d be like, “See you later, dude,” but if you are a glutton for punishment, then have at it. Again, the book is designed to reveal this behavior right away, which it did. Yet you proceeded anyway.

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.

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