In this episode of The Self-Confidence Project, Kimberly delves into the real challenges men face when dating after a divorce, especially those in their 50’s, 60’s, 70’s. Kimberly outlines common obstacles such as insecurities around age and attractiveness, the complexities of feeling attracted to younger women, and dealing with a shrinking social circle. She offers actionable steps on how to move forward with confidence by redefining one’s value, clarifying relationship goals, and enhancing connecting skills. She emphasizes the importance of having a meaningful life outside of dating and provides strategies for men to build rewarding, deeply connected relationships.
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.
And as always, subscribe, leave your comments, and join the conversation—this is a space for growth, insight, and connection.
See you next week,
Kimberly
Here’s the transcript:
Hey guys. Welcome back to another episode of The Self-Confidence Project. I’m your host, Kimberly, and today we’re diving in to the real challenges that men are facing after divorce when it comes to dating, what might actually be holding you back, and how you can move forward with confidence and clarity.
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Because guys, if you’re retired. Or you are divorced, and that doesn’t mean you don’t have a fricking pulse. It doesn’t mean that you’re ready to give up on connection or companionship, but now you are thrust into this world of modern dating and it feels like you are on a different planet. So if you are a man in your fifties, sixties.
Seventies, eighties, who still feels healthy? You’re sharp. You are full of life, but you are struggling to find your footing in the dating world. Then this video is for you. Like I said, I’m gonna break down some of the common and real challenges that men are facing when they’re dating after divorce, maybe.
Which one of [00:01:00] these challenges or obstacles might be holding you back? And of course, I’m gonna talk about how you can move forward with confidence and clarity. Now, before I dive in, of course, my name is Kimberly Hill. I’m a men’s dating and relationship coach. I’ve been doing this now for many years, and, uh, it’s my joy and pleasure to support good hearted men, to find deeply loving relationships.
Now, everybody’s journey is different. Some men just wanna get out there and just connect more effortlessly with great women. Some are looking for, um, really deep companionship. Some men are really interested in marrying again. So no matter what your goal is when it comes to dating or connection or companionship, if you notice that you are struggling or things aren’t really connecting for you, or you just want some healthy perspective and guidance, or maybe you wanna learn a couple skills to just up your game when it comes to.
Navigating the modern dating landscape, then I’m your gal, or it could be your gal. Um, and I just invite you to book a complimentary call with me. We’ll get to know each other, see if coaching is the right fit for you, and if it [00:02:00] is, then let’s do this. We can have some fun. And I’m here to help you connect with amazing women who are going to enrich your live, not to take years away from you.
Okay, now let’s talk about the common struggles that men are facing in dating, especially in their kind of fifties, sixties, seventies, and eighties. Is, and the first one guys, is insecurities around your age and insecurities around your attractiveness. Now obviously, you know, men are going to be wondering, um, as we get older women too, right?
But are women even attracted. To me at this age or women even attracted, uh, to my body in the way it’s changed. And so just like women have insecurities about their bodies and their attractiveness, of course men do as well. And this can be a real stumbling block if you are still kind of comparing [00:03:00] yourself to younger men.
Or you might even be comparing yourself to the younger version of yourself. Yeah. Well, when I was dating, before I was married, I was all these things. And you know, in the height of my last relationship, I was all these things and I was working out and doing this stuff. And so oftentimes, um, there’s this, there’s this beautiful famous quote out there called, I don’t know, the author.
Um, but comparison is the thief of joy. So oftentimes you guys, as you get out there and you date at this kind of new chapter in your lives, you’re still comparing yourself to a different version of you or to younger men, which might be increasing that insecurity around your attractiveness or your age.
And there’s this internal struggle between. Really wanting to have a vibrant partner, but maybe fearing that you’ll be rejected because of your age or because of where you are at in this juncture of your life. So what’s important to remember here, guys, is that [00:04:00] great connection isn’t just about looks great.
Connection has a heck of a lot to do with energy. Your presence and how grounded you are in the man that you are. Today, not who you were 10, 20, 30 years ago, but the man that you are today. So that is, this is just a very common challenge that men are facing now, another common challenge, guys, is just feeling attracted to younger women and dealing with the complexity of that, right?
It is supernatural to have a desire for youthful, vital, beautiful young woman. It is biological. That’s totally normal. However, this can often be paired with unrealistic expectations, or in fact, mismatched emotional maturity, right, and even massive lifestyle differences. And I have a whole other video where I talk about this too, but this can lead to repeated disappointments.
Or it can even [00:05:00] lead you men to just have surface level connections with women because maybe you are going for young women, but you’re not quite sure how to move those connections past surface level. Or the question, you know, is, you know, isn’t, can I attract younger women? But the question is, can I create the type of relationship that I’m looking for with younger women?
That’s fulfilling. That’s aligned. That’s emotionally reciprocal. So there’s this natural desire to wanna be with a young, beautiful, vital woman. Um, but what are, what’s the realistic expectations in terms of the relationship you’re seeking? I. Um, and how are you going about, you know, forming connections and attracting these types of women?
It is a complex issue, right? Um, but it is often one that men in their fifties, sixties, seventies, eighties, are facing as they get out there back into the modern dating world. Now, there’s also a real [00:06:00] common issue, uh, men of having undefined or really idealized expectations of relationships. So it is natural to want to have companionship, to wanna have a partnership.
But what does that mean? What does that mean at this point in your life? Right? Because oftentimes others are unknowingly expecting a partner to fill the emotional gap that has been left by the divorce that you’ve had, and is left by feeling a sense of loneliness. So you might be expecting a very traditional relationship that maybe is what you were creating in your past relationship, but isn’t actually reflecting where you are in your life right now, or maybe reflecting modern values.
So this is hugely important, right? Is. Is getting full [00:07:00] clarity on what you really want from a relationship and what you’re actually able to give. This is key because if you are dating again, right in your fifties, sixties, seventies, eighties, whatever your age is, and you know you are expecting, or you have this vision of a relationship where you’re gonna meet a woman who doesn’t.
Have kids, right? Um, who wants to just move in with you? Who is where you’re at from a career standpoint? Who’s financially independent? Who has time to travel with you? Who can do all these things that you dream of doing in your retirement? Well, that might not, I. Be the true representation of where women are at that are single at this point in your life.
They probably have children or maybe they’re still working in their careers. And so this vision that you might have for your relationship, um, might not really reflect the truth of the women that are out there that are seeking [00:08:00] relationships. So. It’s really important to get clarity on what you’re looking for and to understand that relationship dynamics might have shifted from the relationship you had prior.
And you wanna keep up with, you know, the, the kind of realistic relationship dynamic that you might, uh, be able to obtain at this point in your life. Right? So here, here’s another issue, right? Which is having too much idle time. Which will allow you to have too much mental energy that is focused on dating.
Okay? So when anybody, whether you’re in your career or maybe you are retired, or maybe you just are, no, you’re still working, but you’re no longer in a relationship. Maybe your kids are grown, therefore you have more unstructured time in your life. Okay. More than you had before. If you’re retired, I mean, that’s a huge identity shift.
You have a lot more time on your hands, which can lead to, I [00:09:00] hands can lead to overthinking. It can lead to fantasizing. It can lead to obsessing about women and dating outcomes. And this can create this pressure on the interactions you are having with women and it can lead to feelings of a lot of loneliness and discouragement.
This is, this is natural, right? When you. May have got out of a relationship that you were in for 10, 20, 30, 40 years, even if that relationship, um, suffered towards the end, which led to a divorce. Um, and you probably experienced loneliness in the relationship, that might feel very different than the loneliness you feel being in an empty home with your kids grown and you don’t have 40, 50 hours of work to occupy your mind.
So it can really open up this. Time for you to obsess about dating and obsess about a partnership. And the truth is, man, that the more meaningful your life is outside of [00:10:00] dating, right, the more attractive and grounded you are within dating, right? So what does a meaningful life look like to you? This is definitely something to consider.
Now, another common issue that men are gonna deal with, uh, navigating modern dating. Is this fear of, you know, being seen as like creepy, this fear of being this weird old man or feeling really out of touch. And it’s just so common that the men that I work with tell me, look, I’m, I’m a little bit hesitant to approach women like in public that I’ve never met before, um, because I’m kind of afraid of coming off as creepy or being weird or, you know, being perceived as this like.
You know, just this person that I’m not, and sometimes we’re thinking, well, I have this lack of dating experience and maybe I’m second guessing these normal interactions I’m having with women because maybe I have too much time to hyperfocus on it. [00:11:00] Now, guys, the key isn’t avoiding women. It’s honestly, it’s learning how to express your interest in an attractive woman in a way that is respectful, that is confident, and that is.
Age appropriate to a degree, right? So these are some of the meteor common challenges that men are facing as they get back out into the dating landscape. But there are some other common challenges that may be taking place for you too, and that might be a little bit of isolation or a shrinking social circle, and that might be because your friends are married, that they’ve moved away.
Or people are just unavailable because where they’re at in their lives and their relationships doesn’t give them the same amount of time or unstructured time that you might have. And naturally, it is harder to meet people naturally, um, when you don’t have a lot of effort or intentionality, or let’s be honest, I mean, typically, or stereotypically women are these social coordinators of [00:12:00] relationships, not in all cases.
So sometimes when men are getting divorced, um, you know, friends pick sides or. Naturally gravitate to more per one person more than the other, or those kind of casual, um, you know, barbecues and things just aren’t taking place. And so the social life has shrunk. Or maybe when you got divorced, you know, you left your wife with the family home and now you’re living somewhere else.
And maybe where you decided to move as a couple was a more, a smaller town. So now you’re living in this smaller town and just environmentally you’re more isolated or you live in a more rural area. That was fine when you had the kids running around and your, and your wife there. But now, as a single individual, um, you’re going, this probably wouldn’t be the place that I would choose to be to, to date again, or my options feel really limited.
It. So isolation is a big factor. A shrinking social circle can be a really, really big factor that leads to the sense of isolation. And again, this hyper focus on finding [00:13:00] somebody to fill the gap that you might be feeling socially. And then of course, guys, there’s just limited online dating success. I don’t know how many times, I mean, you know, I’d be a millionaire if I could count how many times I’ve heard men say that they are trying to date online, but they’re being scammed.
So a lot of men are having very limited dating success online, um, for that reason. But also it’s because online dating bios feel a little bit awkward to write sometimes, or we’re not really sure how to talk about ourselves at this point in our lives, or the apps are just feeling really shallow. Um, conversations are stalling online, or you are putting effort into getting to know a woman online, or you’re excited by it, and then you find out she’s a scammer, or you find out she just never, ever responds to you, and that’s reflecting back on you.
It feels like rejection. It’s contributing to your feelings of isolation and frustration and loneliness. But the thing with online dating apps is. You know, it [00:14:00] is difficult to showcase depth and warmth through a screen, right? Um, texting is a great way to miscommunicate and misinterpret how somebody is feeling.
So, um, you know. Moving, dating and building a romantic connection to a tiny little screen, um, is really challenging for a lot of people. Some people, it, it comes a little more naturally, but you know, also we have to think about, you know, you weren’t texting 30 years ago. That just wasn’t a part of communication.
So when you might have been dating previously, you were dating very differently than you are expected to date today. And online dating is naturally very difficult for a majority. Of men. In fact, the last time I looked at the stats, and I know the numbers are really close to what I’m gonna say here, I might not be a hundred percent accurate, but I’m very close.
But it’s like 10% of the men online get about 80% of the likes and activity. The ratio is quite skewed that way. So for a lot of men, they’re just not having, they’re still having fun online. Okay, so [00:15:00] the other common challenge guys that you might be facing is, is just generally unhealed pain from your divorce.
Divorce is a. Is, you know, is a, is a big deal. It’s a massive life stressor and it comes with multiple other life stressors, finances, moving job loss structure around how you spend time with kids. Um, and, and that that’s something that needs to be healed from. And, you know, a lot of people have fear of repeating old patterns.
So the most common thing I hear from men that get divorced is they. Jump into a relationship very quickly with a woman who just seems to represent the opposite of their former partner. And you go from one extreme to another. And I often hear stories that those relationships also didn’t work out, or those women were very toxic, or they got into a toxic relationship because really they got into a relationship born out of low self-esteem.
And then they, they come to dating coaching or to YouTube videos and they go like, what the heck is going on? Um, because look, the [00:16:00] truth is we repeat what we don’t heal and things like trust wounds or men that have either. You know, had affairs on their partners or women that had affairs on, on, on you, um, or just, you know, really losing trust in women because for the last 10, 15 years of your relationship, she was cold, she was distant, she didn’t care about physical affection with you, and you sucked it up to try and do the right thing for the relationship.
But it ended anyways. And now you know, you really have some core wounds to process and you know, you might have built some emotional armor that makes it really difficult to connect with somebody, or there’s a little bit of this trust factor going on, or maybe a little bit of resentment towards women. So, you know, these are, I’m talking a while ’cause these are a lot of challenges that a lot of men are facing with modern dating.
And I wanna just name it to tame it because you’re not alone in a lot of these feelings. And that leads me to talk about the fact that you might just be feeling a lot of shame or embarrassment about kind of being [00:17:00] out of the game. You feel outta practice, you feel like you’re starting from scratch later in your life, and there’s a lot of emotional complexity that comes with that.
But I know that you men, right? Especially the men that I work with, you know, you’re really wanting a great connection. And I know it’s not just about. Sex. It’s not just about that one dimension of intimacy. Um, you’re not looking for surface level companionship either. You are looking for a, a partner, right?
A woman who brings joy and depth and inspiration into your life and vice versa. There’s mutual respect. There’s emotional intimacy along with physical intimacy. There’s shared values, um, and there’s this second, or sometimes even third chance at love. With lessons learned and so I wanna share for a few minutes here guys, how to move forward with confidence if you are in fact going, oh [00:18:00] shit, everything that you’ve said, cam, I feel like there’s some truth in that in my experience, and this isn’t to make you feel bad about it.
It’s to bring light to the fact that these are common challenges that men are facing and you can move forward with confidence. And it honestly starts with redefining your value. Um, you know, understanding where you bring wisdom and experience and steadiness into this world, into relationships. You need to own that.
It’s not about competing with younger men. It’s about leading with your maturity. Because a man who is grounded and has learned his lessons in life and can speak eloquently about the trials and tribulations he has gone through and how that, that he’s overcome those things and the lessons he’s learned, um, women admire men that can share their experiences without, um.
Um, you know, a trauma dumping, so to speak, right? So you know who you are and what you like and where [00:19:00] you’re at, and that’s a very attractive quality. You can move forward by being clear about what you want and being realistic about what you want, what you want. It’s not, I’m just looking for. A nice woman, right?
It’s really defining and understanding with some serious clarity, the emotional, practical, and romantic connection you actually desire and wanna have. Because if you don’t know what you want, how are you gonna get it, right? If you don’t, if you’re playing golf and you don’t know where you want your ball to land, it’s not gonna land there if you’re just swinging at random.
So that’s my great analogy, right? I also want you guys to take some pressure off dating. It’s, it’s funny because a lot of men that I work with, they come to me ’cause I’m a dating coach and then sometimes in our first couple of conversations I’m actually asking them about what they do outside of dating.
And they’re going, well, I just wanna learn how to date so I can find that person. And I’m going, you know what? Sometimes you just need to take the pressure off dating. What makes your life meaningful outside your search for partner. So whether that’s joining groups, exploring new passions, [00:20:00] building and connecting.
With new people or deepening existing friendships or reaching out to lost connections. Let dating be a part of your life, not your only source of connection. That goes for anybody dating at any point in time. Now, you also might need to brush up on some of those connecting skills, and that’s about connecting men.
It’s not about. Performing. So maybe that’s just learning to smile and not feel like smiling at people is weird, right? Maybe it’s just learning to smile or have just some, you know, interesting conversation that goes for a couple minutes or just feeling. Proud to compliment somebody and that genuine presence that you can bring, that focusing on the mindful connecting versus performing.
It’s not performative behavior. It’s not what can I do to win this affection, or what can I do to get this number? It’s just how can I connect with this human being because connection is the lifeblood of our longevity. Right. There’s a, a, a [00:21:00] 80, it’s a 80-year-old Harvard study now that says the number one indicator living a long, satisfying life is the quality of your social connections.
And that outweighs habits like excessive drinking and smoking and exercise that is a bigger predictor of a healthy, long life, um, than those other, uh, than reducing those other elements and guys being willing to grow. So. It doesn’t matter what your age is. If you are fixed in your thinking, you’re fixed in your ideas of things, you will be fixed in your results.
Right? Dating today is different, um, but connection of course is still human, and it’s about learning to show up in this chapter of your life as your most grounded, self-aware self, right? Not trying to act like you were 20 years ago. There’s a disconnection that takes place here, so. I hope this has been helpful.
I really wanted to just highlight these are the common [00:22:00] challenges that most all of my clients are dealing with. I tend to work with a lot of men that are dating, again after a divorce, a separation, um, or even men that are dating again because they are widowed, which is a really difficult. Situation to deal with.
All of these situations are difficult. So if you’re in your fifties, sixties, seventies, eighties, you’re dating after a divorce, you’re dating after a relationship that has ended for various different reasons, and you are in fact craving connection, then you’re not alone. You’re definitely not alone. And guys, you don’t have to settle, right?
You don’t have to be somebody you’re not, or act young. You have to figure out how to be you. The best, clearest, most connected version of yourself at this stage in your life. And to understand what that looks like and how that feels for you. And that’s more than enough, and that’s what’s gonna get you the [00:23:00] success with connection with women in a way that you may not have imagined in a relationship dynamic that might be different than what you originally expected, because.
That, I mean, that’s what I want from my clients. I, I think that everybody out there, we deserve more healthy relationships. Um, it would be great if we could lower that divorce rate, um, and we could have people thriving in their relationships long term. But meaningful relationships do take work and they take a lot of self-reflection.
So I do hope that today’s video was insightful, that it was helpful, that it made you, even if all you did was feel less alone by watching this video, then I’m really happy you tuned in and thank you for tuning in. I, um, I’m excited to make these videos for you guys every week. It’s my pleasure. It’s my honor to talk about things that, you know, sometimes other coaches don’t wanna talk about or talk about in this way.
I’m really passionate about what I do, and so I’d love to hear your thoughts. I’d love to hear your comments. And you know what, maybe, uh, if you followed me to the very end of this video and who, who knows how, how much of a [00:24:00] video each person is willing to watch, but if you’ve stuck with me to the end, um, then I would love for you to drop some advice to other men watching this video.
So what is something that has helped you? What is a mindset that’s helped you? What is a dating? Skill that has helped you? What is a life skill that has helped you feel confident being the person you are today? Let’s share some of those thoughts and comments for other people so that they come to this video and it’s a real source of inspiration.
Um, not just another video, uh, making men feel like they need to radically change themselves to please women, but to really help you understand that. You know, a lot of people are on a journey to find a great relationship, so I’d love to hear your thoughts. Please share them below, and of course if you haven’t subscribed to my channel, if you like the video, subscribe helps me out and it’s lovely to see the channel grow and I look forward to bringing you guys another episode next week.
