Sugar Daddies: The Struggles Of Being A Daddy

Sugar Daddy Confessions: "She was the most dangerous person I think I ever met."

Whether you’re on your third failed marriage or you simply never got around to tying the knot, you may find your 50s a romantic rut. Too old for Tinder, too young to forget about dating. All your mates happily (and boringly) hitched.

All hope is not lost, however. We live in a modern world. Anything is possible. You just have to pitch yourself to the right agency. As one man recently revealed to Refinery 29 on Medium, you can have a lot of fun trying. But, as he also pointed out, it’s a lot more challenging than you’d think – especially when the perception is that the one with the money has all the power – which, he claims, is not always the case.

New York based founder and CEO of a global software company, the man, who chose to remain anonymous, told Refinery 29 journalist Jessica Chou even though his net worth was north of $50 million, it’s been hard to get into conventional dating since his divorce 3.5 years ago, because he travels a lot.

“I’m 50 years old but I probably look 38. I have the mentality of someone in their 20s because I just love to have fun. I jump out of planes, you know? I’m just one of those guys.”

He also couldn’t get into conventional dating because: “My schedule just prohibited it. When I dated conventionally, it always followed the same pattern: Meet a girl, get to know them, they like the vibe. Then I start my crazy travel schedule and there’s an awful lot of stress and texting. When are you coming back? Where are you?”

“So I thought okay, what if I financially support someone and when I’m here, I have the company of someone I enjoy. It seemed like the perfect solution,” he told Refinery 29.

Another attraction, he says, was he “thought it was the only way to meet women who have not been tainted by life,” explaining, “I just found that as women and men age, they get more tainted by their experiences. They create within themselves a negative bias as a standard operating procedure.”

“I went on many dates with women in their 40s, and what I found consistent between all of them was they were immediately looking to find out how I was going to hurt them, even from date one.”

So he decided to try and date younger women, recounting his experiences – and struggles – with three of them to Refinery 29. Here’s his experience with each one.

The Upfront One

“The first woman was the upfront woman,” Anonymous Daddy told Refinery 29. “I met her for a drink and she was very open about the fact that as long as there was some chemistry, she would meet with me and sleep with me for money. Unfortunately, that’s not really who I am. I need more of an emotional connection with someone, even though it might sound weird in that environment.”

The Girl Next Door

“The next woman was someone I would call a ‘girl next door.’ She probably shouldn’t be on the website, and she wants an emotional connection, but she needs financial assistance. So I dated her for four to five months,” Anonymous Daddy said. “After two months she said, I don’t want money anymore, I just really enjoy getting to know you. It really told me she wasn’t looking for a long-term monetary benefit, and that you can have a real chemistry-laden relationship with someone.”

Great, right? Wrong. Or at least – it didn’t last. Why? Over the next two months, the age difference was slammed in our face. I remember I went out to brunch with her and her friends, and someone was whispering, you know, ‘Whose dad is that?’ It didn’t really impact me, but I saw the look on her face. When we talked about it later, she said she wasn’t necessarily prepared for that. So we decided to remain friends.”

The Mercenary

“The third woman I call the ‘mercenary,’ and she was the most dangerous person I think I ever met,” Anonymous Daddy said. “She scared the shit out of me. She would say anything to make you think she loved you. She lied about not having a boyfriend, not living with him, got all the money, gifts, trips, and plane tickets, and when her boyfriend finally threw her out, she came crawling to me.”

“She ended up moving in with me for a while, and then I got set her up in an apartment. Once, I got really ill, and I told her what was going on, and I said, hey, look we need to have a real relationship, or this isn’t going to work. And to this day, I haven’t heard back.”

The man then added, “I spent $200,000 while dating on the site, and about 90 percent of that was on the third woman. I bought her a lot of jewellery. I’d buy her a ring, she would lose the ring or say it got stolen, and I’d buy her another ring to replace the ring. Then her rent, it was $3,500, $3,600 (£2,700-£2,800), plus a security deposit. I know. It was sort of like, hey dude, what are you doing?”

Sugar Daddy FAQ

What is a sugar daddy?

A sugar daddy is someone (usually male) who supports a younger (attractive) person (either male or female) through gifts and money in exchange for sex or companionship.

How can you find a sugar daddy?

Websites such as Seeking Arrangement or Tinder are good places to start if you're looking to become a sugar daddy. The same can be said for sugar babies.

Read Next


A Dating Expert Reveals Why Paying For Your Date Can Ruin Your Chances

Do love interests really care about the size of account?

It’s the age-old argument which is still relevant till this day – does spending your hard-earned cash on women (and men) guarantee you dating action?

There is some primal validity to it – women are naturally attracted to security and resources as much as men are naturally attracted to perky boobs and tanned legs.

As a dating coach I often get this question quite a bit so today we’re going to set the record straight before you go ahead and book that lavish dates on daddy’s credit card.

What Flaunting Money Actually Gets You

For one, it gets you attention, no doubt about it. For two, it gets you followers. Let’s face it – people are attracted to shiny shit, and they will happily ride the money train as long as the doors are open.

If a four-foot tall witchy-looking lass hits me up with “Yo sexy, wanna come on an all expenses paid, champagne flowing, trip to Italy?” I’d say yes. But would I bump the midget? No. No I would not. Would I even follow up and see her again? No way.

That’s a weird hypothetical, but it does explain an important point – don’t mix up attention with attraction.

If you’re throwing your cash at women, of course some will follow you. Who wouldn’t? And they’re probably also going to blow rainbows up your arse to keep that cash tap flowing.

But does this mean they will go to bed with you? Maybe, depends on the girl and if she sees it as a worthy exchange.

But obviously, and as cliché as it is there are points to consider:

  • Are they banging you, or your wallet?
  • Does she actually like you for you?
  • Is she or he with all their gold-digging equipment actually blocking the doorway for a person who would actually contribute to your life, rather than just suckling from it?

All are valid questions which lead us to the below.

‘Less Is More’ Is Always Attractive

I once coached a huge property guy in Melbourne; I’m talking wealth to randomly buying a city apartment on a morning walk.

Yet he played his money down. He never mentioned it. He was careful about taking girls to his house, or them finding out about his business life. But even so – did his value radiate from him? Hell yes.

Within a month he had women fighting over him. Because he was rich? No. Because was awesome. He knew his value, he knew his lifestyle, he knew what he was bringing to the table – he didn’t need to bribe women like some needy trust fund baby.

Compare this to another chap who comes to mind, one that I had the pleasure of meeting one night long ago in a bar in the city. My female friend had to deal with him waffling on about his wealth, job and water front apartment.

She was happy to take share in his endless supply of Dom Perignon, but it reached a point where even that wasn’t enough and she bolted, leaving old mate with a lighter wallet scratching his head.

Avoid Laying A Bad Foundation

Love, sex and connection are not things that you should have to buy or bribe from a love interest; those things should be mutually beneficial things.

If you’re buying her time, her sex, her affection – what foundation does that set for the relationship? You’ve just slotted yourself into the provider role. Cool, but when ovulation hits, it’s not you that her animalistic brain is making her crave. Trust me, I see it every weekend when the dolled up housewives of Melbourne come out to play.

Money Can Never Buy You Lasting Sexiness

This bad foundation doesn’t help you, and it certainly doesn’t help her or your own perception to potential lovers.

How can you help a woman grow and develop if she just lives a perfectly cushy life with your coin? Ronda Rousey has awesomely founded the ‘Don’t Be A Do Nothing Bitch’ movement. She gets it.

The “DNB” in the long-run will likely end up crying on the couch, longing for her slimmer glory days, desperately trying to prevent her husband from upgrading with a newer purchase.

No one needs that kind of drama in their lives. Do it once, do it right.

The Right Way To Go About Things

Go about things how you like, I’m not here to tell anyone how to live their life. If you want to Bilzerian it up, awesome. But if you want girls who you can actually tolerate the company of you after sex, it’s probably not the best strategy.

Personally, I think a chill normal date is the way to start. A drink, a coffee. Boring you say? Well it is if YOU’RE boring.

RELATED: A Dating Coach Reveals The Real Reason Why You’re Single & Dateless

Money won’t make you interesting. If you’re awesome and you click, that’s all you need. Who you are, the success you’ve had, the money sitting in your bank account… you’d be surprised at how much this shows through. And a real charmer doesn’t make a big deal of it.

The Money Shot

Be awesome. Don’t buy girls. If you’re dating a girl and she is awesome – buy her unique cool shit, take her cool places, do cool things with her. Be a gentleman but don’t bribe her into a relationship with you. Don’t bribe sex out of her. You’re better than that and so should your future partner.

RELATED: 20 Things That Will Send Women Running