Here’s what most men get wrong about a dating rut: they treat it as a motivation problem. Push harder, or quit entirely. But a rut isn’t a motivation problem. It’s information — and if you learn to read it, it will tell you exactly what needs to change.In this video, I break down the three distinct types of dating rut I see in the men I coach — online and offline — why each one requires a completely different fix, and the private self-checks that get you moving again without hustling harder or pretending to be someone you’re not. If you’ve been going through the motions, or you’ve quietly stopped without ever deciding to stop, watch this before another month slips by.
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
Dating apps are broken, there’s no real good women out there anymore, and women are incredibly hard to meet. These are the three sentences I hear most from men, and here’s the thing, you’re not entirely wrong. Dating in midlife is a completely different landscape. You guys know this. It’s very different from the one you left when you dated 20, 25, maybe even 30 years ago, or prior to the significant relationship you had that just ended.
And online dating apps are a harder environment than they have ever been, and the dating culture has shifted. There’s a very large grass-is-greener mindset you have to contend with. So some of what you’re up against is very real. But after many years of coaching men through exactly this, I can tell you, we build walls.
We don’t realize it. When you have found yourself in a dating rut, the part of the wall that you can actually do something about [00:01:00] is almost never where you think it is. And a dating rut isn’t just a motivation problem. Many of us think it’s a motivation problem, we try harder. It’s actually information, important information if you listen to it.
Something about how you are dating has drifted far away from why you are dating, and that part of you has quietly stopped cooperating. Now, that part isn’t broken, it’s trying to tell you something. Today, I wanna talk about this. I wanna talk about what happens when you find yourself in a dating rut, what it’s actually telling you, and of course, what to do next so you can find yourself having the dating experiences that lead you to the relationship you’re really here for.
Now, welcome to this channel. My name is Kimberly Hill. 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. Now, if you’re new to this channel and you’d like somewhere to [00:02:00] start, I’ve put together a free guide called Why You’re Not Finding Love.
It’s nine chapters, it’s very direct, and if you’ve been wondering why the same patterns keep showing up in dating, no matter how hard you’re trying in dating and with women, it’s gonna show you exactly why. It’s free, and the link to grab that or to sign up and get it is in the YouTube description. Now, if you have been on this channel for a while, you’re already past the point of reading about this, and you’re ready to actually do the work, Dating Mastery for Men is my self-paced program built specifically for you.
It goes places this channel doesn’t go, and it’s structured to take you from insight to real change. You’re gonna find clarity on the most frustrating aspects of dating and know exactly what to do about it, and how to attract a healthy, loving relationship. That is why you guys are here. Now, the link to read more about that is in the YouTube description as well.
But let’s get into today’s video. What happens when you find [00:03:00] yourself in a dating rut? Well, first thing to understand is not all dating ruts are the same rut. If you misdiagnose which rut you are in , you might just apply the wrong fix, and you could even dig yourself in deeper. Now, most advice is gonna say one of two things.
Try harder, okay? You need to be doing more in dating or you just need to take a break altogether. And to be honest, either one of those can be right or wrong. It’s really depends on what rut you’re actually in. And this isn’t just about dating apps. This is all about being, you know, online, out in the world, or using both.
These ruts will show up in all of these domains. The terrain changes but the pattern doesn’t. Now, I see about three different ruts Of course there could be more, but I bet money you’re gonna recognize yourself in at least one of these. Now, the first rut is what I call the [00:04:00] effort rut. So this is the guy who, maybe this one’s you, who’s out there doing everything you feel you have been told to do in dating, but you’re getting nothing back.
So online it might look like this. You’re on four or five different apps at once. You’re sending lots of messages to women. Mostly you’ve gotten to a point of figuring one message works and you’re copying and pasting that to different women. When a conversation does get going, you try very hard in that conversation, you follow a formula, you say all the right things y- that you’ve read somewhere recently, and none of it really lands because none of it comes across as genuine.
From the inside, it feels like a lot of effort is coming from you, but it isn’t. It’s actually spaghetti at the wall , okay? It’s throwing a lot of stuff up there and just hoping for something to work out. You’re just seeing if something sticks. Now, offline, this effort rut is the same pattern [00:05:00] in different clothing.
You’re saying yes to every single event, every meetup, every invitation that you get. You’re being everywhere. You’re hoping proximity alone will do the work for you. You’re showing up with no real intention beyond being out there. Then you go home wondering why nothing is really coming of it. And here’s what’s hard to see from the inside of either of these versions.
Presence without intention doesn’t register. A message that could have been sent to anybody reads as no interest. A man that’s circulating a room hoping to be noticed isn’t connecting with anybody. The problem was never how much you’re doing, it’s that none of it is specific or genuinely yours. So if you have found yourself in this effort rut, the fix is counterintuitive.
It has nothing to do with adding more [00:06:00] effort. It’s all about redirecting it. Cut your activities in half and double your specificity. Online, that means fewer matches or fewer messages that are chosen more deliberately, messages that could only have been written to this one specific woman. And I know that’s difficult, ’cause I’ve seen a lot of women’s profiles and- Many of them give you very little information to go on, so sometimes you do have to think and be a little creative.
Now offline, that means fewer commitments. It’s chosen because you genuinely want to be there, not because you think, “I have to be there to meet somebody.” And when you’re somewhere you authentically want to be, conversations will stop being a performance, and they actually start feeling better or more natural.
So you don’t actually wanna burn yourself out by effort that isn’t directed. So a little private self-check for you guys is nobody has to see you do any of this, right? [00:07:00] Before you hit send, you ask yourself, “Could I send, uh, this message to any woman on the app?” If it’s a yes, maybe don’t send it. Now, before you accept an invitation, you might wanna ask yourself, “Would I want to be at this event even if no women were here?”
Motion and progress are not the same thing. The effort rut is what happens when you confuse them Now, rut number two, guys, is the meaning rut. Now, this one’s a little sneakier because from the outside, it might look like things are working. You are meeting women, you’re going out on dates, and every single one of those dates feels hollow, interchangeable, like you’re rewatching the same episode.
Now, I did have a client that was in this rut. He kept chasing the same type of woman, women who, if he was being very honest with [00:08:00] himself, were never gonna be right for him, and he kept getting the same poor outcome. So here’s what stopped me. There were good women, genuinely good women, paying attention to him, showing real interest, but he would dismiss those women, and the reason why is because their interest was freely given to him.
There was nothing to earn or win. He had confused the feeling of chasing with the feeling of attraction. Let me repeat that, ’cause this is more common than you think. He had confused the feeling of chasing with the feeling of attraction. If a woman wasn’t making him work for it, some part of him decided she didn’t count.
Now, if that is you, this rut isn’t happening on dates. It’s in your selection and how you show up. [00:09:00] Because when you chase, you ultimately end up in a audition. You spend the whole date trying to be picked by her. You try to be pleasant, agreeable, performing like you’re a great job applicant. And auditioning is…
it’s exhausting. It’s hollow work. No wonder every date feels the same, because you were never actually truly in any of them. Now, the move here is a single question that you can ask yourself privately before any date you go on. What do I wanna find out about this woman tonight? Not, how do I make this woman like me?
What do you want to learn about her? Is she kind under pressure? Does she ask about your life or only talk about hers? That one question can really flip you from performing to evaluating, from being an applicant to being an equal. And women will feel the difference in a [00:10:00] man who’s assessing fit versus a man who is seeking approval.
It’s one of the most attractive shifts you can make, and it costs you nothing Now, rut number three is the quiet quit rut. Now this is a, a one that a lot of guys won’t admit to, so I’m gonna describe it and you can nod your head and say, “Okay, yeah, this is probably me.” So in this rut, you haven’t actually decided to stop dating, you have just stopped.
So the apps, you haven’t deleted them, they just sit unopened. You’ve stopped accepting invitations. Your world has quietly shrunk down to work, home, routine, or work, gym, home, or work, kids, home, gym, routine, this kind of thing. Now, if a friend asked, you’d say you’ve been very busy, and you have been, conveniently, with everything except for dating.
Now, usually this traces back to [00:11:00] one specific disappointment that you’ve had. So oftentimes men do the quiet quit because a promising connection that you were very excited about fizzled out, and then the drift started from there without you ever really intentionally saying, “I’m gonna just take a break.”
You just did this quiet quit. Things are active, but you’re not actively involved. Now, that is not a true break. A break is a decision. This is a drift, and drifting is only truly … and is the only truly wrong answer because that’s how six months, if not longer, of your life kinda disappears without you really saying, “I chose to spend them that way.”
So you end up thinking, “I’m not having success with dating,” even though deep down you know you haven’t really been doing anything. It’s just that you never made an intentional decision, decision to step away from it. Lot of men end up here. It’s the quiet quit. [00:12:00] Okay? So here’s the move. Make a decision tonight.
Two honest options. Option one: take a real break. That’s okay. You are welcome to take a break from dating. It can be very frustrating and exhausting, and it can capitalize a little bit too much of your time and energy. If that’s what you need, be deliberate about it. Put an end date on your calendar.
That’s legitimate, and sometimes exactly what an individual like yourself might need. I’ve hit walls in my own life and business and in dating previously where I was pushing very hard and only coming up against resistance, and what I needed was not more force or a new strategy or a new tactic.
Sometimes we just need to clear a little space, and all of a sudden the insight we need or the connection we need comes to us. A chosen break that creates space is intentional, but a quiet quit or a drift doesn’t. Now, the second option is re-enter dating with a small, [00:13:00] low-stake action this week. One thoughtful message, one invitation accepted, one evening spent somewhere new.
Not a campaign, a single deliberate act that puts you back into motion. Either chores- choice, guys, is respectable, but refusing to choose isn’t. You don’t wanna end up kind of drifting along. Now, what do all three of these ruts have in common? The thread running through all three of these is that a rut is often a little bit of our self-respect leaking out slowly.
In the effort rut, you’re tolerating a process that is treating you as disposable, and you might even be inadvertently treating women the same way without even meaning it. Now, in the meaning rut, you’re abandoning yourself on every date by performing instead of showing up. And in the quiet quit rut, you’re breaking a promise to yourself [00:14:00] so slowly you never really have to notice it.
Now, getting out of a rut was never about hustling harder, trying more. Many men that I’ve worked with, that I’ve had on this channel watching my stuff, you guys try very hard. You put a lot of effort into a lot of this. And what I really want you to take from this is dating in a way that you can respect, you yourself, not your friend or what someone else is doing.
It’s dating in a way that you can respect online and in person, wherever you’re meeting women, where your effort means something, your presence feels very real, and your choices are actually choices. Diagnose your rut. Make your move, guys, because that’s the work for you this week if you’ve found yourself in one of these three ruts.
Now, of course, before I go, first I just wanna thank you for your time. I mean, there’s a lot of YouTube channels out there talking about this stuff, and if you’ve landed here, I genuinely thank you for being here. [00:15:00] And of course, if something has connected with you today, you have lots of options, so take today’s content and run with it. Download the free guide. Look at the Dating for Ma- Dating Mastery for Men course. The link to all of my information is below in the YouTube description, and I’ll see you guys all next week. Ciao.
