Everything You Ever Wanted To Know About The World Of 'Sugar Daddy' Dating

Business Insider

Eight years after it launched, sugar daddy dating site Seeking Arrangement is still generating controversy.

There's still a taboo around an older man paying lavishly for the company of a much younger woman — while the women are sometimes portrayed as either victims or prostitutes.

But not every Sugar Baby is a 20-something trying to pay her way through school.

We spoke with "T", a 40-year-old consultant who lives in Virginia. T makes $150,000 a year, and uses the site to find what she calls "mutually beneficial" relationships. She talked about what it's like to be a Sugar Baby, her past Sugar Daddies, and if the site is really as bad as it seems.

Why did you sign up to be a member of Seeking Arrangement?

I have been in two long-term mutually-beneficial situations in the past. My intention was to go on the site and meet like-minded people.

How many people on average reach out to you a day on the site?

It varies. It can be anywhere from 15 to 20, to as many as around 100. A lot depends on the time of the year, actually.

What's your profile like?

My profile tends to intimidate, it's kind of a weeding out process. The Sugar Daddies that may approach other women would not necessarily approach me.

They wait, and if I approach them they say, "I saw your profile, but I was a little intimidated so I'm glad you reached out to me."

What makes it intimidating?

It could be the photos, or my height. I mean I'm 5'10'' — if you put 6'' Louboutins on me, I tend to be a little scary.

Or it could be my education level. I've had a lot of men comment on how highly educated I am.

And then when you get to the meat of my profile, you can see it's not my first time at the rodeo, and that I know what I'm looking for. I'm very blunt, to the point, and no nonsense.

Would you consider yourself a typical Sugar Baby?

What most people would commonly assume to be a Sugar Baby — someone in their early 20s, a college student, easily influenced and manipulated — that is not me.

I'm more of the "Grand Dame," if you will. I'm older, but then I've found there's something for everybody and every taste, just like any typical dating site.

Is there a typical type of Sugar Daddy?

The men that I tend to attract are very dynamic, successful, been-there-done-that kinds of men. They don't want the typical airhead that they have to lead around.

They want somebody who they can speak intellectually with, talk business with, and who they are proud to be seen with by their business compatriots.

But also someone who can twist them into a pretzel in the bedroom.

What is a typical arrangement like on the site?

Everyone on there is going to be looking for something different. You're going to find a lot of people who are just looking for basic relationships.

They want somebody that's going to be loving towards them, and that will take care of them.

What is your typical arrangement like?

For me specifically, I've come to the point in my life where I appreciate a man who knows how to take care of a woman. I like being spoiled and looked after. 

But also, I'm working 70-80 hours a week, so if he's working 70-80 hours a week too and we're both traveling, somebody's going to have to cut back on their work schedule.

I'm at the point in my life where I'm willing to do that. So that's where the allowance comes in, or the stipend. I work crazy hours so if you want me to be on your schedule, you're going to have to accommodate me and make sure that I'm taken care of financially.

What do you look like?

I'm in my 40s. I'm 5'10'', blonde — I've been told I look a bit like Sharon Stone. I don't know if that's a good thing or bad, but I guess it's in the eye of the beholder.

Do your friends or family know that you're on SeekingArrangement?

Yes. My family does, and some of my friends do. I have a very close-knit group of friends.

Do you currently have a Sugar Daddy?

I have a couple of gentlemen who are interested, and I guess who are "applying" for the position.

How many Sugar Daddies have you had?

I've had two long-term arrangements that were about four years each. They were off and on. One was married, one was not.

Both of these individuals were very high-profile people, very famous — one of them was a little bit of politics and a lot of business, and the other one was in entertainment and dabbled a little bit in business as well.

I'm still friends with both of these gentlemen to this day.

The man who was married — did you ever have an encounter with his wife?

His wife knew about me. She wanted the power, the prestige, the money, the social standing — but she didn't want anything to do with him. It was somebody who was equally as well-known as her husband.

We had an interesting luncheon when I first met her. And she said, "Look, this is the deal: Be discrete, take good care of him, and just understand my position, as I understand yours. As long as we're fine with each other it shouldn't be an issue."

Have you ever tried any other online dating sites?

I have tried other sites. Oh god, I tried Match.com and it was atrocious. It's just the dregs of humanity, it's horrible.

On MillionaireMatch.com, the men don't know what they want, plus 90% are lying through their teeth.

I have also tried SugarDaddie.com and I find it's okay, but I would say the majority of the men on there don't know what they want or they just want a relationship.

Why do you like arrangements?

For me and my lifestyle, I find being in an arrangement to be highly erotic. I don't do it because I need to, I do it because I want to.

Have any users made you feel uncomfortable or sent you ridiculous messages?

Yes. Don't drink and text, and don't drink and put up a profile. It's incredible.

But the staff is very vigilant about it. If someone is proposing something really uncomfortable or something illegal, they're done. They're off.

Has there ever been a moment where you have had trouble accepting a gift?

No. Definitely not. I come from the position that I believe that every man should treat every woman like this anyway. I think we have lost that as women. We've allowed men to digress into this mentality that we should take care of them, and there's no chivalry.

If a man feels that he wants to give a gift — if he's thought about it, taken the time to give from his heart, and he wants me to have it — I don't find it to be unusual at all.

What's the most extravagant gift you've ever been given?

A house. I've also gotten cars, very expensive jewelry, and furs.

What do you wish more women knew about the site?

I'm a Southern lady, so I was raised to believe this is how gentleman should always behave. Once you become intimate with someone they should take care of you, and look after your needs and your wants.

If you want to work that's fine, but being taken care of is not giving away your right as a woman to be independent. Men should want you to have nice things.

What does the media get wrong about SeekingArrangement.com?

The first thing people want to do is hang the term prostitution on this. And it's not. I can tell you very truthfully that most of the men that I have met are not necessarily looking for sex, they're looking for companionship. They're looking for someone they feel is an equal, someone they can rely on, and who they can trust.

I mean, yes there's the old-world-style mistress, but that is really not the end-all-be-all to it. It's just a very small percentage.



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