When will dating stop being so hard for Gen Z?

Forget the Hollywood fantasy of smirking Casanovas armed with killer one-liners and perfectly tousled hair under neon lights.

I used to date Millennials until they hit the “expiration date.” The youngest Millennials are 29 now—aging out of the sugar scene and into therapy. (The more bitter ones will be in this answer’s comment section)

And let me tell you, fathers in those days weren’t just protective; they were full-blown sentinels guarding the gates of hell.

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It’s a strange, paternalistic partnership, and God help me, I actually enjoy it.

Enter Gen Z, a new crop of frustrated souls, but the frustration is eerily familiar.

That’s the gauntlet we came from—the crucible of humiliation and raw, unfiltered chaos. The one we survived.

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Now, sugar dating? That’s a different beast. It’s refreshingly laid back—a strange, unspoken contract of mutual honesty and boundary-free conversation.

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Every word out of your mouth felt like a confession at gunpoint. You’d be sweating bullets, trying to sound like some paragon of virtue, knowing full well he was picturing you as the scumbag who’d ruin his daughter’s life.

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First came the mental gymnastics of when to call.

But when you finally did muster the nerve to dial, you’d hit another goddamn wall:

In the 90’s - you didn’t have a choice - cold approaching was just what you had to do.

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All of this is GOOD NEWS! It should seem obvious, but from your perspective, its not.

If you’re serious about learning how to approach women, then, I’m here to help. Again, I am not selling anything, I don’t want your money - I’m good.

I’ve ridden this wave long enough to see a generational shift.

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As a 48-year-old Sugar Daddy, I’ve seen the battlefield from both trenches, and let me tell you—it’s a hell of a vantage point.

That means - you’ve got almost ZERO competition. You need to start trying. I’ve got dozens of videos with GenZ women complaining about you not trying. Extremely hot - Gen Z chicks.

Buckle up, because this is a cocktail of hard-earned wisdom, poor decisions, and a willingness to wade waist-deep into the absurdities of modern dating.

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They ask for advice, and there’s no jealousy poisoning the well.

Save it for your incel group.

If I’d had the choice back then, you can bet your ass I’d have taken the easy way out. But here’s the ugly truth, my friend: all this convenience comes with a price. The grit, the effort, the goddamn humanity of it all has been gutted, leaving behind a sterile, hollow shell.

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Too soon, and you’d look desperate.

And you would. Oh, you absolutely *would*.

What I am is a dude who’s actually concerned with this problem, and, I can help. For free.

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Either way, the clock was ticking, and every passing second chipped away at your already tenuous grip on sanity.

Virgins

her dad. If she lived at home—and most of them did back then

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In short - you’ve just got no game - but its not your fault.

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They spill their secrets, their heartbreaks, their schemes, and their dreams.

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Then it’d come—the rejection, sharp and merciless, cutting through the smoky haze of the room like a knife through your soul. But that wasn’t the worst part, oh no. The worst part was the *spectacle*. Her friends would swoop in like vultures, eyes gleaming, ready to eviscerate what little was left of you. You weren’t just rejected; you were a public execution.

First of all - I am not selling anything. I am not a “coach.” I don’t want your money. I’m good. I’ve got videos of me in my Lamborghini Huracan, and Ferrari California to prove it.

And now? Now, you just swipe left or right. No awkward calls. No interrogation from dad. No sweaty palms gripping the receiver like a lifeline. It’s all neat, sanitized, and gutless.

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These girls, they open up in ways you don’t see in “normal” dating.

It sucked. It was a bloodsport—a gladiatorial brawl for your dignity where the odds were stacked against you, the crowd was jeering, and the lions were already licking their chops.

I wasn’t suprised…The girls I date are stunners, the kind of women who turn sidewalks into catwalks. Of course guys don’t approach them. Guy’s DON’T approach dimes—they’re terrified.

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It’s an epidemic.

If there are less guys approaching women - to the point where 50% of guys your age

For a solid decade, I was neck-deep in the pick-up artist scene. Yes, it works—and by "works," I mean becoming a swaggering, dopamine-addled caricature of a man. You learn the tricks, the lines, the rhythms of a social dance that’s as contrived as a daytime infomercial. But here’s the rub: it turns you into an unholy blend of desperation and bravado—a full-tilt douchebag with a veneer of charisma. Eventually, you start to hate your own reflection. That’s when I bailed.

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If you’ve got a reason for NOT approaching women - don’t watch my videos…

The only mercy was time—time to stew, time to replay every stumble, time to promise yourself you’d never be that stupid again. And then, inevitably, you’d do it all over.

And let’s say, by some unholy miracle, you got her number. Don’t start celebrating yet, cowboy—you were still deep in the trenches.

he’d be the one to pick up.

They’d answer with a voice like gravel and demand to know your name, your intentions, your SAT score—hell, maybe even your blood type.

I listen. I guide. Sometimes I protect.

Wait too long, and she’d forget you even existed.

So, I dug in, peeled back the layers of this sociocultural onion, and yeah, I’ve figured it out. I know why men aren’t stepping up. And more importantly, I know how to fix it.

No, it was more like strapping on a blindfold, stepping into a minefield, and praying you didn’t explode into a million pathetic pieces.

**guys don’t approach me!**

Dropped out of the dating scene

And there was no goddamn escape hatch. No apps to swipe your failures away, no digital armor to protect your ego. You were exposed, raw and bleeding, stranded in the harsh fluorescent light of reality. You’d sit there, a monument to your own humiliation, drowning in the bitter cocktail of shame and regret.

But as I listened more and started connecting dots, I realized this wasn’t just a hot-girl problem.

Right now, your natural instinct is to give me a “reason” why you can’t.

Both groups—Millennials and Gen Z—are grumbling the same refrain:

That first "uh, hey" would leave your lips, shaky and desperate, and she’d glance at you like you were a stray dog begging for scraps.