What It’s Really Like To Date A Sugar Daddy

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When my best friend from school uttered the words, “I want a sugar daddy,” the image of her with a Hugh Hefner lookalike came to mind.

I didn’t know whether to feel sorry for her or proud that my assumption was partially true, as the first sugar daddy she met bared a striking resemblance to Wallace Shawn from “The Princess Bride.”

She met Dave*on Seeking Arrangement, a popular website for sugar daddies, sugar mommas and sugar babies to connect and create mutually beneficial relationships.

The site has a strict profile photograph policy where sugar babies must show the goods (aka, their faces).

My friend Jessica* wanted to keep her identity private, so she uploaded a photograph of a giraffe.

Naturally, this was blocked.

She chose another, one showing her face, and her inbox was soon flooded with messages from interested guys. One lived nearby, and after messaging back and forth, they decided to meet for dinner.

When she met him in-person, she was struck by how much shorter and older he was than he initially described.

Suffice it to say, the attraction was very much one-sided.

They spent the first part of the date sitting in his car talking, and he rubbed her nipples through her shirt. Then, he took her to a fancy restaurant.

The whole experience was very “wham-bam-thank-you-ma’am.” But, she left it with $100, so that had to count for something.

She closed down her profile soon afterward, but as of late, she has been considering giving it another try.

Jessica’s experience is one of many. You never know who could be a sugar baby; it could be the girl sitting next to you in class or the graduate who has thousands upon thousands of student loan debt.

Whatever the case, for those considering taking the plunge into the fascinating, but sometimes risky, world of being a sugar baby, here is a no-judgment pro and con list.

Pro: You choose the arrangement.

There is a huge misconception around how the term, sugar baby, is simply a cuter way of saying “prostitute.”

It’s not true.

Seeking Arrangement and other websites of this kind view the arrangement like a business deal. It involves outlining what each partner can expect and how they will give and receive.

At the end of the day, sugar babies can enjoy the freedom of calling the shots and choosing whom they have s*x with.

Con: A lot of the men are married.

We spent a lot of time browsing through different profiles, and for the most part, the guys were honest. They were either up-front about being married, preferred not to say or even had joint profiles with their wives.

One profile we found fit this third category, as it featured a photograph of a man and his wife on their wedding day.

We were shocked to see this, but it made sense when the text below described how they were looking for a sugar baby for the both of them to spoil.


Pro: There’s the possibility of traveling the world and having new, exciting experiences.

This is undeniably one of the biggest perks that attracts people to this lifestyle.

Sugar babies have the opportunity to explore the world, have exciting new experiences and get wined and dined on a regular basis, and it’s all on someone else’s dime.

It’s also not uncommon for sugar babies to get weekly or monthly allowances, and have their sugar daddies or sugar mommas pay their bills and other debts.

They also may get spoiled with lavish gifts. (Hence the term, “sugar daddy.”)

Con: Can be difficult finding decent guys

Those who find the “dad bod” attractive will be pleased with the type of men who are usually on these sites.

There are bound to be a few cute ones, but it’s probably best to not get your hopes up. Not all 50 plus men are rich and sport six-packs.

My friend realized this when the guy she met was a little too generous with himself in both his profile picture and physical description.

Arrangement or not, being a sugar baby still means entering into some sort of a relationship, and attraction to the other person is a big part of that. It shouldn’t just be one-sided.


Overall, whether you choose this style of dating or not, it’s important to understand the risks involved.

Oh, and when choosing a profile picture, go ahead and save yourself the trouble by not choosing one of an animal.

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