When will dating stop being so hard for Gen Z?

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.

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 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.

Where are the big girls? This is the first time I've seen a bigger lady boy and that's awesome .. you should post more of them here, nothing wrong with a thick black lady

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

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

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

Why are people saying that Trump is fat when he is an athletic 6 foot 3 and 215 pounds?

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

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.

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.

What are the most common signs that a partner will cheat before it happens?

are either

Too soon, and you’d look desperate.

Virgins

What is the naughtiest fantasy that you've lived out?

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.

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.

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

Why did my ex move on so quickly?

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.

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

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

How does a person become transgender?

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

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

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.

What should a young woman do to control sagging breasts?

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.

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

Dropped out of the dating scene

Summer Game Fest 2025 LIVE: Everything announced during the gaming showcase - Tom's Guide

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

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

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.

What are some lesser-known facts about Bollywood and the Indian film industry? Are there any insider secrets that only those in the industry would know? How reliable are these claims?

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

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

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

What are some alternatives to wearing a bra? Why do some women feel pressure to wear bras even though there may not be any benefits?

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.

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

Why is Taylor Swift re-recording her albums?

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

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

Save it for your incel group.

Boeing Stock, Up 64% From April Low, Upgraded To Buy As Trump Game Piece - Investor's Business Daily

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

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.

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

Is 1500 calories enough for a 5’3 15-year-old who is non-active?

First came the mental gymnastics of when to call.

I listen. I guide. Sometimes I protect.

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

What can I say to a scammer who thinks he loves me, but I don't want to be scammed?

he’d be the one to pick up.

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.

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.

Have you ever had sex with your husband's friend in front of your husband? Please tell about it and elaborate.

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

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.

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

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.

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.

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

It’s an epidemic.

**guys don’t approach me!**

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

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.