When will dating stop being so hard for Gen Z?

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.

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.

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.

'Kindness isn't a weakness,' Steve Carell tells Northwestern grads at commencement - Chicago Sun-Times

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.

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.

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.

How does someone start doing urban exploration?

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

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)

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

How did you get to be a leftist?

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

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

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

How do I become an intelligent man?

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

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

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.

Why does my mother care about my sister more than me?

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

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.

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.

What is the most gay experience with your dad?

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

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.

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

How do you handle your mother-in-law after you heard her talking badly about you in the next room?

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

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.

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.

What are some life hacks for living on your own?

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.

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

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

What happened to everybody's thick skin? It used to be that people really didn't get offended, now however, everybody gets offended by the least little thing.

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

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

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

How does it feel to have sex with a 40 year old curvy aunty?

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.

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

he’d be the one to pick up.

Is it true that schizophrenia can sometimes be a demonic attack or black magic?

are either

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

First came the mental gymnastics of when to call.

Report: New Development in Trey Hendrickson Contract Situation - Sports Illustrated

Dropped out of the dating scene

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

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

I have a bad reputation and need help. What should I do?

Save it for your incel group.

I listen. I guide. Sometimes I protect.

Don’t put your loser negativity in the comment section.

Is there a possibility that we are living in a simulation and that there is a concept of rebirth?

**guys don’t approach me!**

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.

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

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.

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.

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

It’s an epidemic.

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

Virgins

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

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.

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

Too soon, and you’d look desperate.