Is Anyone Actually Having Fun Dating in 2026?
Is anyone actually having fun dating in 2026? I'm going to share my experience right now, which I hope will help you feel less alone, because it seems like dating ought to be fun, right? It seems like this should be a beautiful part of life — trying to get to know someone, making a connection, beginning your love story. Doesn't that sound like something that should be awesome? Is it just me, or has the process of even trying to date become miserable? When I was in my 20s, fifteen years ago, I remember there was some pain for sure, but I don't remember it feeling like this.
Right now, I'm waiting for a reply from a woman I've seen the last two nights, asking when she's free again. She replied to my first message in ten minutes. Now it's been over an hour. I said, "Seeing you the last two days has been fun and I'm wondering when you're free to do something with me again." Nothing for over an hour. Maybe she has to check her schedule. And isn't there a story I could tell myself here? Like, "Ooh, this is fun — the uncertainty, maybe something will work, maybe it won't." It doesn't feel fun. It just feels stressful. It just feels like now I'm distracted. Thank God I have an outlet in making these videos to at least talk about this, because if I wasn't talking about it, if I wasn't trying to help somebody else, this whole experience would seem like just unnecessary humiliation and torture. My God.
I remember going out in high school and having some fun, but I also remember it was pretty stressful back then too. I just want dating to be fun again, but I'm not even sure how to do that. It's so full of disappointment and failure. And yet I know that the results of dating are awesome. I had a fifteen-year relationship that just ended last year — a marriage, kids, turned into divorce and shared custody and all that. And the fruits of the dating were awesome. I do remember having fun dating my ex. I remember really enjoying most of our dates and looking forward to the dating. And now I can't even get someone to agree that we're dating, or call it dating, or plan a date. The confusion, the chaos, the insanity of it all. It's just like, God, I hate this. Isn't there a way for this to be fun? I feel like at this point I could get into another relationship and I wouldn't have enjoyed the process at all. And I'm not even sure exactly how I need to change to facilitate that. At least I do have the awareness now that I want this to be fun.
"I'll Never Ask a Woman Out Again" — So How Long Did That Last?
I'm tired of not having women reach out to me. I made a video saying I'm looking for a wife, and I titled it "I'll Never Ask a Woman Out Again." So how long do you think that lasted? Well, since that video, I talked to this woman — I actually got kind of fixed up with her, but I already knew her, and then we were at the same event. And she said she wants to be pursued. Where she's from, the men pursue the women. So out of the two of us, it's certainly easiest for me to change. But then all the Owen Cook people will be like, "Oh, you lost your frame now." But can't I just compromise with somebody? Can't we meet in the middle? I was talking to somebody else and they said dating ideally should be meeting in the middle, where both of you are willing to reach out first and both of you are interested in seeing each other. I was talking to a woman last night, and there was another guy there who said, "Yeah, I feel like women choose us." And the woman said, "I want to be chosen too." I'm like, God, man — I want to choose a woman too, but no woman seems to want to be chosen by me, at least so far. But then all of that can change rapidly, right? I just want to enjoy the process. I'm tired.
Off the Apps and Into Events I Hate
I've been going out to all these social events, trying to just meet women in their natural habitat instead of using dating apps — which are an unnatural habitat, superficial beyond belief, and pay-to-win on top of that. So since I deleted the dating apps, I've been hitting the social scene hard: Thursday, Friday, Saturday nights out doing stuff. Stuff that I hate. I hate listening to kirtan song ceremony stuff. I hate it — music I don't want to listen to. The only reason I even care about going is for the conversations I have with people, but I have to sit through two hours of music to get an hour of conversations. And at the last one of those I went to, there was a woman there that I liked. She said hi to me, and I felt like garbage the whole time afterwards. And of course, I had deleted her number. She doesn't message me. Then she's not at the event this week.
I went to an ecstatic dance last night. Apparently the woman I bought a ticket for — the one whose reply I'm waiting on now — had a great time. I didn't. I hated it. It was, I don't know, torture? Well, I can picture a lot worse than having to listen to a bad DJ who can't transition worth anything while you're just standing there thinking, "What was that stupid transition? Come on, anybody could have done that transition better." And we did this contact improv class, which was just terrible — crawling around on the ground. It wasn't fun at all. I'm like, well, this is stupid.
What's Actually Fun to Me
So when I expressed some of this, one of the people there asked, "Well, what's fun to you?" Seeing somebody join my family — that's fun. And you might ask, why would you want to join that? So you could talk to someone who understands. Someone who's going to listen. I've seen that something like one in six Americans doesn't even have a single close friend, and around twenty percent of people say they've felt lonely in the last 24 hours. The only thing that gets me through this show of misery is that I have so many people I can talk to about it — close friends, family.
I was just talking to a guy on the phone, and he was telling me about this other guy. This other guy is about ten years older than me, and I know him pretty well. He's a good-looking guy, and he's a crowd-pleaser. Most people like him. He's got a few haters, but most people like him. I'm not as much of a crowd-pleaser, believe it or not — I'm a polarizer. Half the people love me, half the people hate me. I go around and there are people who can't stand me. This guy doesn't have too many people like that; he seems to be mostly well liked. And with dating, he has all these women over and throws a party — and yet he's single. He's gone out with a bunch of these women, and he says they're all crazy. I don't know if that's my experience — I definitely have some overlap with that — but I'm like, can't this just be fun? I'm about to just lower my standards so much. But then I was so critical of that in the past, and I've seen that go horribly wrong.
At least the one piece of value I got out of this today is that I know what I need to offer people, because there are a lot of people who have fewer people to talk to than I do, and I could be one of those people for them. That's why I made my membership. As a member, you can literally talk to me every week on Zoom, face to face or on audio. That's powerful. That's very meaningful. And I want to hear more people's experiences, because I think what makes dating so miserable is being stuck in our own experience. Just hearing that another guy — one I would think dating would be easy for — is struggling too. It's not easy for him. And I don't know if that makes it better or worse.
It Was Easy for My Ex
It was real easy for my ex. I guess she just immediately went on the dating apps and got into a relationship with the first guy she met. But she doesn't talk to me about it anymore — you can imagine why, with Mr. I'm-on-YouTube-and-talk-about-everything. Part of the reason she wanted to get divorced is that she was tired of her whole life being broadcast on YouTube, including our sex life — and there was a lot of sex. I sure miss that. We were having sex every day or every other day, right up until we got divorced. I sure miss that, but I don't just want to hook up with some random girl either. I want to enjoy this journey of dating. I'm tired of it. I'm tired of being so miserable.
Awareness Is the First Step
I guess just knowing that I want to enjoy the process is the first step. In my experience, you can't have change without awareness — it's hard to change unless you're aware of what you'd like to change first. I'm so tired of dating being miserable. I'm so tired of every single thing that happens, instead of it being exciting. I do have some euphoria sometimes. I felt really good about 48 hours ago, after I went on a date with my ex-girlfriend, thinking, "Ooh, we have a lot in common, and maybe there'll be something here." And now I'm just like, what was I thinking? I don't even want to message her at this point, but I don't want to go back on Hinge either. And this woman is the only option I even know of.
I'm killing the rest of my social life besides AA meetings, because I'm so sick and tired of being out at these events where my only purpose is to meet a woman — because I wouldn't go there for myself. I wouldn't go to an ecstatic dance for myself. You know what I'd do? I'd put on some Deadmau5, some music that actually doesn't suck, or whatever music I want, and I'd dance to it. People were telling me at the ecstatic dance last night, "Yeah, people are just here to do their own thing." I'm like, why don't you do that at home? At home I can dance and do my own thing. I'm going out to these things — like a run club — trying to meet people, and I don't want to run. All right? I don't want to run.
Two Hours of Tennis With a Terrible Attitude
I played tennis for two hours today with a rotten attitude, and the dude destroyed me. He beat me 6-3, 6-2 — and this is a guy I've beaten before. So why was I so miserable?
The Ticket Story
Well, because I went out to this event, and there's some comedy material here. I paid for a girl's ticket. At least I paid for this woman's ticket — and then she literally invited the other girl, the one who had been over to my house before, the one whose texts I hadn't responded to because I didn't know what to say to her. I'd decided she was too crazy for me. So literally the one I paid for invited the one I was talking to before, and I'm thinking, you've got to be kidding me.
Then I felt bad that I didn't reply to that girl, but my close friends said, don't reply to her. Stop this with her. She's a disaster. It's not going anywhere — you and her aren't aligned. And meanwhile I'm thinking: I just want to stay home and talk to people on Zoom. I'll go to AA meetings and parent my children. I'll go to a yoga class and do my techniques. God, there's got to be a better way, man. I just want to have fun.
Can't Dating Be Fun?
I would hate to get into another relationship and feel like it was just miserable getting there. I keep thinking: at what point can I open my heart and have fun and be excited about this process? Every time I start to get a little bit excited, I get dumped on — whether it's her being way too crazy (not a little bit too crazy, but way, way past reasonable crazy — I can handle a little crazy, maybe even medium crazy), or they just stop responding, or it's the "I'm busy" nonsense, or the half-lukewarm interest. Every time I start to feel a little excited, I just get crushed. But maybe I won't in the future.
Can't this be fun? Can it be fun? I want it to be fun. Don't you want it to be fun? Don't the girls want a dating story that's fun — fun for them? Can't we all just somehow make this whole process enjoyable instead of miserable?
I'll at least say this for some of the dudes I know who are just sleeping with as many women as they can: they're ridiculous. They'll do anything to get laid. In my experience it's both inspiring and sad and pathetic all at once. And one of the guys who was living that lifestyle just disappeared. That lifestyle clearly is not sustainable or satisfying in the long term, but at least it provides some enjoyment in the short term — although it's often short-lived and comes with a high price tag.
What I would just love is for a woman to see my videos and appreciate me being a real man — one who's honest, who wants a family, and who's doing everything to be able to provide for a family just on YouTube, really helping people instead of ripping people off like a lot of YouTubers do. How cool would that be? That would be awesome. And funny enough, right as I was saying this, a woman actually joined my membership. What are the odds of that? Not zero — but a rounding error away from it. I can fantasize all I want, though, right?
This Is What "Above Average" Looks Like
And here's what's sad. I think I'm above average in looks — I'm not going to claim I'm some Chad or anything, but I'm lean. I don't have a six-pack, but I used to be 80 pounds overweight, and my abs look about the best they've ever looked. I'm lean, I'm healthy, I'm energetic. I have YouTube, which some people see as a status symbol — I've been famous, people run into me who've watched my videos all the time, and lots of times people don't even remember that they watched my videos a decade ago. I'm probably in an easier situation than the average man. And that's what really makes this crazy: this is what it's like to be above average. What are the guys below me doing? Well, a lot of them are just not dating or even trying. I understand why you would give up in this environment. It's nuts, man. It's nuts.
There's got to be a better way, and I'd like to think the better way is clear, honest communication like this. I did practice this with the woman I talked with.
Her Reply Came In as I Was Finishing
And then — oh no — right as I was wrapping this up, she got back to me. Let me react to it honestly, because I really didn't want to do this. Her message: "Let me get back to you on that. My next three…" Her next three weeks are booked. Man, I'm so tired of this. I shouldn't even be on Messenger — it's so stupid. She doesn't have a job, she needed me to buy her a $25 ticket, and her next three weeks are booked? This is so bad. I wish I could say this is so good — if I enjoyed feeling like garbage and being humiliated, maybe it would feel good. "Let me get back to you on that." You know what? I'm done.
But hey — aren't I an awesome guy to talk to? Seriously, I'm a guy you could talk to and think, "I can tell Jerry what I'm going through, and Jerry will understand." And you know what? I might be able to help you more than I can help myself. Ironically, a lot of times it's actually easier to help someone else than it is to help our own selves.
If you want more raw, honest stories like this one from my dating journey, they're all collected in my Dating playlist. That's it for today.