Twitter CEO Jack Dorsey Gallivanting With Model Half His Age

I thought Mr. Burns was more into Smithers.

That beard (the one on his face) is atrocious.

Tim Cook is more than a decade and a half older than Jack Dorsey. Jack dating this girl is equivalent to Tim Cook dating a 39 year old, which would not cause any stir whatsoever.

Are you really getting your tits in a tangle over this OP?

He's a good looking 44 yo who is richer than God and she looks in her late twenties/early thirties. What's the issue?

I agree about the beard R2. It's out of control.

That beard is an ant trap.

Because she lets him call her racial slurs while doing her anally and pulling her hair.

She a 29” bust.

I didn’t know Jack was into ironing boards.

[QUOTE] He's a good looking 44 yo who is richer than God and she looks in her late twenties/early thirties. What's the issue?

She’s 23. Did I not already state her fucking age right there beneath the thread title? And the issue is the double standard applied to gay men.

R8, are you still saying that Tim Cook would cause a stir by dating a 39 year-old? I think you’re wrong.

He’s gay and deeply, deeply closeted… “allegedly”

David Geffen brought his 28 year old BF to the freaking White House. There is no gay double standard as long as you’re rich enough.

She's not 18 or 21, she's 23. He's 44 and rich.

Most people won't have a problem with this because we all know exactly what this is.

I applaud her. Get money, girl!

I'm 59 (but look younger!)

if I won the lottery tomorrow, I'd hire a personal trainer/massage therapist/companion; late 20s; 30s; even late 30s or 40s

Someone to get me in shape, provide companionship; if he sucks as massage, I can always hire someone else.

We'll go out and have fun as things start to open up; once I get in shape and felt better about myself I'd hand him a HUGE bonus and send him on his way and hopefully stay in touch through text or social.

That purse that she's carrying in multiple photos is a bundle of $100 bills.

Tone it down.

Swimsuit model is code for paid companion

He looks like he smokes a lot of pot. I'd still happily fuck him though.

Swimsuit model is code for prostitute.

These tech bros are revolting.

I lamented to a friend that my time with a guy who was putting himself through school was 'transactional' -- where that word came to me, I don't know.

She said every relationship is transactional.

She had a point.

It's true to a point. Particularly in the American way of thinking R19. People often seek to see what they can get out of something.

I find it refreshing that she’s not one of those generic blonde stick women.

the guy I saw off and on for a few years must have been a psych major or something; he got inside my head, pushed me further than I thought I could go, but not further than I actually could...he rocked me world, kept me from falling in love with him, and made me feel less alone; made me feel like I wasn't a freak.

I'd give anything to see him one last time.

Oh. My. God.

A rich man dates a beautiful woman half his age. I never ever, not in a million years, thought I'd see this. I'm beside myself in shock. The audacity of it all.

I mean, how can I go on?

[quote] He's a good looking 44 yo

I want to dispute that. I think he was really cute and great looking when he was 30. But something happened with him that had him age rapidly. Not even talking about the homeless look he is displaying. Let's just assume all barbers refuse to do business with him. But what about the face? That is not the face of a man in his healthy forties.

How about a look from the other perspective? Why is a 20 something woman dating a guy double his age? Because chicks will fuck a pile of goo if it had money and status.

^ double her age

R7 Spoken like a true fat frau. Her 24” waist goes perfectly with her 29” bust. Clutching your pearls under you neck rolls that someone has the audacity to be slender.

Think of the children!

[quote]. But something happened with him that had him age rapidly.

R24, he got really into "fitness"

[quote]After all, the tech CEO doesn't eat breakfast nor lunch. Dorsey reveals in an interview that his extreme diet only requires him to eat seven meals a week. ... Over the weekend, sometimes the tech billionaire would not eat anything at all. He is also a vegan and practices the Paleo diet.

So he's a vegan who barely eats!

Here's a photo from when he likely used to eat 3 meals a day, every day instead of one a day every day.

The Tom Hanks Castaway cosplay is not working for him

[quote]I find it refreshing that she’s not one of those generic blonde stick women.

True. But alas still a stick woman. My titties are big than her's and I'm a dude!

OP - do you disapprove of the age difference, and if so why? Do you disapprove of gay guys dating men half their age? I don’t get your point here.

Too much money makes you crazy. Example #5,268,323.

When exactly did age differences become such a big deal? Older men have been dating younger women (and men) since The Flintstones times. Why is it all of a sudden a problem now?

"Older men have been dating younger women (and men) since The Flintstones times."

1960-1966?

[QUOTE] OP - do you disapprove of the age difference, and if so why? Do you disapprove of gay guys dating men half their age? I don’t get your point here.

My point is that when gay men want some young ass, it shouldn’t be frowned upon.

OP, I came here to say: "Thank you for using [italic]gallivanting[/italic]." Love that word.

Jack turned out nutty. Will he be the modern-day Howard Hughes?

R36 -- As an eldergay who dates younger guys (20 - 30 years younger) I find it is mostly frowned upon by a certain group of commenters here on the DL who just seem hung up by the whole "Daddy" scene. In real life nobody much gives a shit.

What ages are we talking about exactly, R38?

20 and above, R 39; over the last 20 years. Currently 58 with as 29 year old boyfriend.

[quote] Dorsey Gallivanting

Of course he is.

He's Irish and Irishmen drink and gallivant.

It's not the money that has made him go crazy, it's what the NSA has commanded him to do with his beloved twitter. Obviously.

He gets to deduct 1 year from his age for each billion $ he owns!

I don’t care about the age difference. What creeps me out is his obsession with black culture. It’s like he fetishizes it. Also creepy how this girl looks similar to his previous girlfriend.

Oh, and I still think he’s gay.

[post redacted because linking to dailymail.co.uk clearly indicates that the poster is either a troll or an idiot (probably both, honestly.) Our advice is that you just ignore this poster but whatever you do, don't click on any link to this putrid rag.]

If I was a rich gay, that’s how I’d control my harem of twinks. Put them in nice houses, and inside each master bedroom on a wall ensconced in a recessed picture frame is the deed to the house with my name on it.

He is an intensely creepy fucker.

I imagine him liking anal.

Every man likes anal.

Flora is the NEW Jean Peters!

R50 I don’t know what that means.

Look her up, R51. Wikipedia is always educational.

Hot body and probably a nice dick.

But that beard! I expect him to say "Excuse me sir do you have a couple of dollars you could spare, I haven't eaten since yesterday"

I think he's uncut for some reason

That beard suggests he wears Kleenex boxes for shoes around his barely furnished, enormous mansion.

Do you think Jack likes missionary or doggystyle?

Didn’t know Jack could be pleasant looking

Do-able

He lied under oath. Will they go after him?

Jack likes showing off his feets.

From 10 years ago

R59: yeah, perjury

Not so good

[quote]When exactly did age differences become such a big deal? Older men have been dating younger women (and men) since The Flintstones times. Why is it all of a sudden a problem now?

Yeah, what IS this all about lately? People are so hung up on it. If everyone is above the age of consent, then I don't see the issue. Some people are acting like there is a law somewhere about age gap limits that others are breaking.

As another poster said though, it's probably all online ranting. I don't notice it in real life either. I myself have dated men 20+ years older than me before.

OP, get a life.

R59, this is for you

Oh no

Protekkk duh childruns

Those tits make mine look like inflated funbags!

She makes Calista Flockhart look busty!

“BUTTWIPE OP ATTEMPTS TO REVIVE THE WORD ‘GALLIVANTING’’ WITH ONLY MODERATE SUCCESS’

He has the hawt hobo look. Sometimes you just want that.

I like the word "gallivanting" as well.

Dorsey was really cute in his late twenties - he almost still looked like a teen choirboy.

You wouldn't expect a rich man to date old.

they both like to starve themselves. they get along great!