In this episode, Kimberly Hill explains why men returning to dating after divorce often rely on a mental checklist that turns dates into audits, causing them to miss the most important signal: how they feel around a woman. She argues that compatibility isn’t found in perfect answers but in the space between two people, and that “interview” energy creates tension and performances rather than real connection.
P.S. If you’re a man navigating dating after divorce, don’t go it alone. My free masterclass was made for you—learn how to rebuild confidence, attract the right women, and avoid common post-divorce mistakes. Watch it here.
Ready for tailored support? Book your 1:1 dating strategy call with me here and let’s map out your next steps.
See you next week,
Kimberly
Here’s a mistake that almost every man I have known has made when he starts dating again after a divorce. Or reenter dating after the end of a long-term relationship. He builds a list and it’s not always a list on paper. Sometimes it’s a list in your head that the woman you next get into a relationship with has to be emotionally available.
She has to want to relationship. She has to have a good, decent life of her own. She certainly shouldn’t be bitter about her ex. She should be kind. Feminine, honest, physically attractive, um, looks after herself and good with kids if she has any. And here, I get it. None of those things are wrong, and those are very reasonable things to want from a woman.
But here’s what happens. You go on a date. And the whole time you’re not actually there. [00:01:00] You are auditing. You are running this woman’s answers through the filter you built with your checklist and you’re trying to figure out if this woman actually qualifies for the position of your next girlfriend. And what happens, guys, is that you miss the one thing that is actually telling you everything you need to know.
Which is how do you feel around this woman? And that’s what this video is about. It’s not a better checklist for you guys. It’s a completely different way of knowing if the woman you’re dating. Is a good match for you. Now, welcome to this channel. My name is Kimberly Hill and I’m a dating and relationship coach for men.
I support good-hearted men to attract deeply loving relationships and go on to maintain those relationships. I work privately with men on a one-on-one basis. Um, so if you’ve been watching my channel for a while, I’ve been skimming through some of my videos. Maybe you’re resonating [00:02:00] with the content or you’re thinking, Hmm, maybe at this time to reach out to Kimberly for support, then you are certainly welcome to book a complimentary call with me to see if we are a good fit to work together and if I could be of help to support you in your dating journey now.
Why does the checklist fail? Well, the checklist approach makes sense on the surface, and that’s because, look, you’re a man that has lived through a relationship. You’ve been hurt. Maybe you even were blindsided by your ex and you probably missed some red flag. In the beginning of getting to know this woman that you now really genuinely wish you had caught, and so this time you are gonna be a little smarter about it and you’re gonna be a little more deliberate.
You’re going to vet women, you’re gonna screen women, you’re gonna make sure that the woman that you get to know. Isn’t going to create the same pattern or dynamic that you had previously. That’s a smart thing to [00:03:00] do. But the problem is that when you use a checklist, it is a cognitive tool that is being applied to an emotional experience, which is dating, as you know, and compatibility, true compatibility.
It doesn’t live in somebody’s perfect answers. It lives in the space between you. So I want you to think about it this way. You could interview a woman who literally checks every single box and still you feel absolutely nothing with her. There’s no real ease. There’s no spark between you two. There’s no real sense that you can fully exhale around her, and then you could meet somebody who doesn’t tick half your list at all, and you feel more with this woman than you have in years.
So the checklist simply can’t measure that, and it was never designed to. There’s also a more subtle problem, so when you’re in this mode of I need to vet screen or audit [00:04:00] women, she can feel this, right? And it actually creates this kind of weird low grade tension like she’s on a date. But for some reason she feels like she’s performing for a job she didn’t know she was applying for, and that dynamic does not give you useful information because now you’re watching a performance, not actually meeting a person.
And you guys know what it feels like if you’ve been on the other end of that. So. Really vetting somebody is not an interview. What it is, is an experience that unfolds with time. Now, I know you guys are all going to say to me. Something like, well, Kimberly, I simply don’t have time to invest six months into somebody new, only to find out that she wasn’t right for me anyways.
Now what happens if that goes on five times in a row, I’ll be dating for the rest of my life, which is fair pushback [00:05:00] and it’s a fair question that might be. Rising up in your mind right now, and I wanna be clear about something because I think there is a real distinction that does need to be made here.
I am not telling you to say in something that feels wrong if you are two or three dates in, and you can already see that this woman’s values are fundamentally different from yours if her lifestyle is genuinely incompatible with what you want. If you’re noticing things that. Honestly concern you, but you’re ignoring them ’cause she’s attractive.
Well, this is not what I am talking about. That is not vetting. That is. Hoping that she just like radically changes as you continue to get to know one another. What I’m actually talking about is something very different. I’m talking about the woman that you’re with. When there is genuine interest, when there is genuine compatibility on the surface, there is this genuine potential that you can see and you feel the urge to rush to a verdict.
You really wanna fast track this decision. [00:06:00] You wanna know by month two whether she’s the one so that you just don’t waste any more time. And that is the pattern that I want you to slow down. It’s the pattern that many of us get into, myself included. It’s a little bit of that anxious dating. And here’s the truth, you, um.
You actually do develop a felt sense of a person relatively early, right? You know this not on the first date necessarily, but within the first few months you start to get a read of somebody. Um, you get a sense of whether a woman has integrity, um, if she’s actually emotionally stable. That one can take a little time, but you will feel that within a few months you can get a sense of whether she treats people well.
Is there some real substance? You know, unfolding here, or is this really surface level appeal and you do not need a year to answer those questions? What takes longer? What actually requires time is the [00:07:00] deeper layer. Can we handle conflict together? Do I feel fully, uh, myself and safe with this woman? Uh, does this relationship have the kind of foundation that could actually hold the weight of a real life together?
And then that is the part that many men rush and that is the part that costs you guys now. You know that you’re not in your twenties anymore. You know that the decisions you make now carry more weight, more history, more complexity, often children, more emotional stakes, and this is not a season of your life for impulsive choices or letting chemistry override.
Your actual clarity. Now, the men that I have worked with who have built the healthiest relationships the second time around all had one thing in common. They gave themselves permission to be [00:08:00] patient, not to be passive, not indefinite patients that never actually eventuates into something, but they stayed curious.
Instead of anxious, they let the relationship reveal itself instead of forcing it to perform. We often want to have clarity early on because it relieves something within us We think, you know, now that. I am committed to this person or that we are, you know, gonna give it a go. I can finally like relax and be myself.
But that’s kind of counterintuitive. You should relax and be yourself leading up to that decision because when the right person shows up, well it’s not because you ran her through the gauntlet of questions, it’s because you’d really been paying attention to yourself and to the woman you’re getting to know.
So, to be clear. If it feels wrong, trust that leave. [00:09:00] That is your felt sense working exactly as it should be. But if it does feel right, if there is something of substance here, then do not let urgency talk you out of taking the time to actually know her more beyond this. Now before you commit to someone who could become your partner for the rest of your life, which is your goal here, if you’re on this channel, then slow down.
’cause that is not fear, guys. That is wisdom. So here is a reframe that I do want you to sit with when it comes to. You know that question you’re gonna ask yourself, well, like, how do I know if this is the right person this time around? Now, vetting is not about finding out whether somebody is good enough.
It really is about paying attention to how a relationship feels as it develops and trusting what you are noticing along the way. That is it, right? That is ultimately the whole thing that I’m talking about here. But I do wanna be specific because when I say pay attention to how it feels, you guys are going like.
What are you saying, [00:10:00] cam? That sounds so abstract. Um, so you do need to know what you are paying attention to, and the questions that matter guys are not the ones you’re asking her. I mean, they matter to a degree, but what really matters is the questions you are asking yourself. So after spending time with a new woman, not just the first date, right, but across multiple weeks and multiple contexts, then I want you to check in with yourself on questions like, do I feel at ease around her?
Or am I performing a version of myself? When something bothers me in this new dating experience, do I feel like I can actually say it? Or am I shoving it under the rug, right when this woman is having a hard time? Do I actually want to show up for her? Or does it feel like a burden that I didn’t really sign up for?
Do I feel respected, not just liked? Do I feel [00:11:00] respected, and is this woman curious about who I actually am? Or does she seem more invested in who she wants me to be? Right? So none of those questions can be answered on a first date. None of them. They reveal themselves across time and across experiences with this woman.
So they show up. Pardon me? When you’ve seen her stressed out, right? When you’ve had your first minor disagreement, when you’ve met some of her friends, when the novelty of like the first kind of. Month or few dates has actually softened a little bit, and the real texture of the connection starts to show itself.
And that is what time does. It doesn’t just build trust, it builds information that no question and answer session or checklist on a date could give you. So let me be clear about the things that actually matter as you’re getting to know a new woman, and none of them require a. Single direct question.
They [00:12:00] do require observation across time. Now, the first is, how does conflict get handled? You guys know you need to see this. You know it, and you think, well, we have nothing to fight about ’cause we’re so perfectly aligned. Oh, you just wait. You just wait guys, because it’s a comment. So you don’t need to manufacture conflict to test her.
I highly advise against that. It’s gonna show up naturally. Um, miscommunication, A difference of opinion. A moment where one of you gets frustrated over something. So when that happens, pay attention to what is going on. Does this woman go very cold? Does she escalate very quickly? Does she get very defensive and make it all about to her, or does she stay in this conversation and stay connected to you as a man and a person and work through it?
Now, she doesn’t need to handle conflict perfectly. But she does need to be participating, right? So the moment that you see. How she responds is worth a thousand [00:13:00] answers to, are you emotionally mature? Because every woman will tell you, yes, I am emotionally mature, and then the proof needs to be shown down the road.
Now, secondly, how does this woman treat people who can do nothing for her? That means the waiter, the parking attendant, her assistant, if she has one right the way. A human being, woman or man treats somebody in a position of less Power is not incidental. It is a character reveal that happens whether you’re aware of it or not.
So be mindful of this. Now, you also wanna notice. What your own nervous system is doing around this woman. So this is one of the most underrated signals that many men dismiss. Many women dismiss it, and it’s not attraction like, do I feel really extracted to her? That is different. Let’s put this to aside for a moment.
What I mean is, do you feel calm around this woman? Can you even think clearly? Do you feel like you can take up space, share your opinions, say no, be [00:14:00] imperfect. Without bracing for a reaction. Now, I wanna caveat here, because if you’ve been in a prior marriage where you tried to open up and then you got like vitriol right from your ex, you probably learned to brace yourself, right?
And then not to speak up moving forward, because that just was ugly, ugly conflict. So even with a new woman, you might still have that pattern in you where you’re like, woo. Who, I’m gonna say something. I’m gonna share an opinion. I’m gonna say no and I’m who, I’m kind of bracing for this reaction. You might do that, but how she responds, what is really happening there?
You gotta, you gotta see her behavior. Right, because a dysregulated nervous system around someone you’re dating is not always chemistry. You might be like, oh, all of these like feelings might mean something. Or I, I’m just bringing in this old pattern into relationships expecting something to go wrong when this woman is actually revealing that she’s quite levelheaded and accommodating and kind to me, and I’m going like, this is [00:15:00] weird.
I’m not used to this. Right? So there’s a lot to learn from here in terms of how your nervous system is feeling around this woman. And whether you’re bracing for a reaction because that’s a pattern of yours, or you’re bracing for a reaction because you’re getting a negative reaction to literally just being yourself or saying no or being imperfect.
Right? Be mindful of this. Now, I also want you to pay attention to whether the relationships have. Two things. Ease and depth, right? Because some connections can feel really easy. Oh, it’s so easy, but they’re shallow. You might have a great time, but nothing’s actually getting said or revealed. Whereas other connections feel intense, but exhausting because they’re always emotionally loaded and they’re always a little bit.
Fragile. So what you’re looking for is a relationship that can be both easy or have ease, and also have depth and be real. It’s light and it’s serious, it’s fun, and it’s honest, and that combination doesn’t happen overnight. But you do start to feel its [00:16:00] early signs within the first few months of getting to know someone that again, you’re with because you’re genuinely curious about the potential.
Now, I want you also to be mindful of this one. This is a big one. How do you feel when you are not with this woman? Do you feel settled? Do you feel super anxious? Do you feel good about. The time you spent with her earlier today or yesterday. So these quieter moments of reflection between the times you see each other often carry more honest information than the time you spend together.
Because the performance pressure is off. So really tune into what is happening in your mind, in your heart, in your soul, in your body, in your gut, when you’re not with this woman. Now, I wanna say this as clearly as I can. Time ain’t your enemy in dating, okay? It’s actually your [00:17:00] most valuable tool. Now, if you’re a guy that’s coming out of a long marriage.
You’re, you’re naturally gonna feel a sense of urgency to figure things out fast, right? Because you kind of quickly wanna know if this person is right for you and you, you don’t wanna waste time. I mean, nobody wants to waste time in dating. And so that urgency that it creates is very understandable. But rushing the getting to know you process, the vetting process, the screening process, it doesn’t protect you, it bypasses it.
And real compatibility shows itself in seasons. Right. You need to see how this woman handles stress, how she shows up when she’s not feeling good or at her best, what she’s like when the relationship stops being completely shiny and brand new. How the two of you recover from a hard conversation and none of that is available at month one.
And sometimes it’s not available at month three either. And so that doesn’t mean you wanna drag things out indefinitely, of course not. But it does mean resist the pressure to reach a verdict with this new woman [00:18:00] before the evidence has come in. And if you guys had done this the first time around, I guarantee you, you would’ve made different choices and you know that.
So stay curious, stay present, let the relationship show you rather than, um, trying to force it to prove itself because there is a real difference between being patient, right? Letting it unfold naturally. And of course then being passive, you know, patience means you’re still in this, you’re paying attention, you’re continuing to show up, um, and you’re letting the clarity come as it comes.
So here is something that does not get said early enough in this conversation. Um, vetting works both ways. You guys know it. So while you’re paying attention to how this woman is showing up, she’s experiencing how you show up. And one of the most honest things you can do is you reenter dating after a significant relationship is take your own darn readiness for relationships.
Seriously, not in a self-critical way, just an honest way. [00:19:00] Are you available emotionally? Not just logistically can you really let somebody in, or do you find yourself keeping a very careful distance and then wondering why things? Stall, you know, are you really bringing your actual self to this dating process?
Um, or are you bringing a very well managed or curated version of yourself that is ultimately actually designed to not get hurt? So the men who vet screen get to know women the most effectively aren’t just watching these women. They’re watching themselves. They’re noticing when they’re showing up genuinely and when they’re actually managing everything.
And that self-awareness is not a weakness. It’s actually what makes healthy relationships possible. So here’s the summary. Don’t audit. Throw away your checklist. I mean, in the grand scheme of things, you kind of, you already know what you want from a relationship. So instead, start paying attention. Trade the checklist for being present and trade [00:20:00] the interview for having a good experience and trade the verdict.
For being patient, patience is a virtue. So the goal is not to find a woman who is passing your tests on the first date or second date or third date. The goal is to find someone who in real time, across real moments, in real conditions, like the road trip you might take, we’ll actually make you feel like the relationship is worth being in.
And that is not something you can think your way into. You have to show up to get there. Thanks guys. Okay.
