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Pretty Please Daddy, With Sugar on Top? An Interview with a SeekingArrangement Sugar Baby by Jenna Homen

Relationships on Your Terms: Where beautiful, successful people fuel mutually beneficial relationships.

This is the mantra repeated on, an online dating website dedicated to matching up wealthy Sugar Daddies and Sugar Mommas (Proud Family, anyone?) with their desired Sugar Baby and Sugar Baby Male counterparts.

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The Founder and CEO is MIT graduate Brandon Wade, who conceptualized the company in 2006. On his personal website, he attributes his “shyness and lack of a dating life during my teenage years” as the motivation for his current business. SeekingArrangement boasts a high ratio of eight Sugar Babies per Sugar Daddy, noting in Hunger Games diction that the odds are [ever] in your favor. The arrangements are supposedly “no strings attached, mobile friendly,” and good for “ideal relationships.” On the flip side, Sugar Baby perks include the chance to have “financial stability, find a mentor, date experienced men and be pampered,” through activities like “shopping sprees, expensive dinners, and exotic travels.” Currently there are 3.6 million active members in over 139 countries, 2.6 million of which are Sugar Babies and 1 million are Sugar Daddies and Mommas.

SeekingArrangement also makes a point to emphasize safety by adding a background check option, and delineates Sugaring from prostitution by deeming it a lifestyle choice, not a profession. While a Sugar Baby is a woman who wishes to date financially secure men and can be selective, a prostitute isn’t afforded that leisure.

But when one is entering the Sugar Daddy/Baby relationship, it is difficult to deem it a completely free choice. The SB often has financial difficulties which have led her to using her body for money – I doubt an affluent, wealthy girl would make herself a SA profile. So is SeekingArrangement a euphemistic coverall for prostitution? And is prostitution wrong? Are these women victims or are they empowered? 

One can argue that there is a sense of female agency and choice when selecting an arrangement, so it seems unfair and counterintuitive to play the victim card. However, if a female is entering an arrangement because of financial woes, it could be said that her choice is less free because of external motivating factors. The website openly acknowledges that Sugaring is a way for women to avoid student loans, and even pays for ads to appear on search engines whenever a woman types in something like “help for tuition” – making it hard to pretend that this is merely a “lifestyle choice.” Masked by the allure of higher levels of safety and a dimension of choice and selection, the site allows the woman to feel like she’s in control...even when she might not be.

I spoke with a twenty-two-year-old woman who has been using Seeking Arrangement to generate supplemental income with the hopes of saving enough money to go back and finish her college degree abroad – here’s what she had to say.

How did you hear about Seeking Arrangement?

I was working at a hotel and a drunk older man came up to me with a beautiful blonde girl on his arm. He started telling me I should check out the site and that I’d be great for it – kind of hitting on me. After I looked it up to see what he was talking about, I made an account and out of sheer curiosity started talking to people. I think it took about 6 months until I actually met someone in person. I dicked around on it for a while.

What made you actually go through and meet with someone?

It was someone who lived in the same area (in the mountains) as me and we were emailing back and forth for a while. Because he lived so close and we had talked for such a long time, I felt like it was a good icebreaker situation. We didn’t really discuss how much money I’d be getting or anything. He basically said every time we see each other, regardless of if it’s just dinner or if we sleep together, I’ll get a “donation.” He didn’t say how much, but that was fine with me because I just wanted to check it out. He had a daughter and he was in software. He was predictable.

How many men do you message?

I message with twenty plus men on the site itself per week. Of those, I move to an email conversation with maybe half of them. If both parties feel like they’d like to meet, we then exchange phone numbers and meet face-to-face, usually in a bar. Here’s the way I have it set up. I have a fake name on my profile and I blur out my face in my picture. I also have a fake Gmail account based on the fake name – I usually give people that if we’ve been messaging on the site for a little while. If I want to talk more direct, I’ll give them my phone number, but usually email first. I have a couple friends and family members who are aware of what I do and I usually inform one of them when and where I am meeting a new person.

How many men have you met up with, both total and regularly?

In my six months of consistent Sugaring, I’ve met probably eight men. I currently see four men, although some are more sporadic. There’s one I see a couple times a week, even if it’s just to grab a beer after work. I also meet with a lawyer and a high profile CEO about once every two weeks. I just met a new one last night, and I am expecting that to become a consistent arrangement.

How much money do you make from each arrangement?

I make anywhere from five hundred to two thousand dollars per meeting. Seven hundred to eight hundred dollars is typical. 

CEO Brandon Wade and his wife, Tanya.

What type of men do you typically encounter on SA? I’m sure there are some general tropes.

Well, it depends. There are THOUSANDS of high tech executives. If you work in the tech industry, I guarantee someone you know is on the site. One of the best things about being in the Bay Area is that there is an abundance of wealthy, successful and intelligent men here. Because the standard of living is so much higher, they’re able to pay more. I’ve met lawyers, doctors, men who retired off their huge inheritance... married men, single men, divorced men, widowers.... there’s a huge demographic. You have young entrepreneurs who claim to make a decent amount of money. Some can get “Diamond Verified,” meaning that they have their income validated to prove they make the money they say they do. One of my high-profile arrangements is a Diamond. I feel secure about SA because, for the most part, I know the demographic that’s using it. It’s Silicon Valley. I actually steer clear of people who don’t fit into that demographic, almost as a safety precaution. I understand the tech world and the money in it. It makes sense to me.

How is the arrangement typically decided?

It totally depends on the circumstance, but usually the basics are laid out via email. I like to have some mention of the financial “donation” I expect to receive prior to meeting, as that is often a more awkward conversation in person. There are also a lot of escorts on SA and it’s important to present myself as a normal girl while still making mention of the financials. Definitely a struggle, but a lot of men bring it up on their own accord. The great thing about SA is that each arrangement is so different. Some want a full-fledged “girlfriend experience” without the hassle and commitment, so they like to take me on day trips and stuff like that. With these men, sex isn’t necessarily their top priority. Others want to meet at a hotel restaurant and head straight upstairs before you can say dessert. I’ve been approached by plenty of SB/SD duos that are looking for a third, as well.

She pulls up her emails. This one is from a guy who has an Asian sugar baby and they want to have a threesome.

He would pay me two grand for that. He also likes to take pictures so he’d want to photograph us too. He’s very clear. Not all of them are this clear, especially the shy guys and first-timers. This guy, “L”... this is the Diamond Member. He said he wanted a “genuine friendship, honest communication, and great sex. What about you?” He’s a really busy dude though. He said “I propose we start with two grand per visit the first couple of times, then ten grand a month plus travel and shopping if we like each other.” A big part of it is playing it cool. He ended up paying me three grand for one visit

What makes a good arrangement?

Mutual respect and communication. If a man is married, you need to know. If you’re seeing four other Sugar Daddies, he needs to know. It’s important to make sure that everyone has the same expectations so you avoid complications in the future. Also it’s important for me to be able to find something attractive about the person – even if I don’t find them physically attractive, I usually can find a sexy, sensual side of them. This is what keeps me actively engaged in these encounters and makes your advances believable. And trust me – if you’re not enjoying yourself, if there’s anything “fake” about your presentation – the man will know and not like it. I’ve actually made close friends from SA. If you weed through the weirdos, there are a lot of wonderful people there.

What do you enjoy about it?

I enjoy essentially everything about it. I get to meet incredibly successful, intelligent men, learn from them and also serve as an escape to them. People have asked me if doing this affects my weird as it may sound, I’ve never felt better than when I’ve been sitting in a bar, doting on an older man who can’t stop smiling because he feels incredibly masculine, desirable. I’m incredibly confident (one of the best attributes for Sugar Babies) and have become even more comfortable in my own skin thanks to SeekingArrangement. And of course, I’ve made a LOT of money.


How does this affect you on an emotional level?

Keep in mind that I consider myself incredibly good at keeping sex and emotional impulses separate, so this question is probably more useful coming from someone who struggles with that more. The nice thing about SA is that the cards are all out on the table – both parties recognize that their “arrangement” is not a relationship, but you can reap a lot of the same benefits. It allows me to live an independent life and date “normally” while still developing close friendships with successful men. It’s also wonderful to get laid consistently without the hassle of a standardized relationship.

What are some requests that you get from men?

Anal is popular, of course, because men from the baby boomer generation consider it just the right amount of taboo. There are some men who want extremely vanilla sex and others who want you to be as off-the-wall as possible. I’ve had men ask to take photos of me during our encounters, who have wanted to kiss my feet all night, who request very specific lingerie items to be of the best things about being a Sugar Baby is getting a glimpse at the inner desires of so many different people. It really teaches you that no two people are the exact same.

What are your hard limits?

I haven’t really thought about this, really...I am very sexually open and am willing to experiment with essentially anything as long as there’s a level of trust between my partner and myself. I’m fine with light BDSM (I got to be my first Dom the other day, it was thrilling), anal, toy play, and so on. I wouldn’t call my limits “hard,” but much more fluid and derived from individual experiences. Something I’ve said no to? Watersports.

How do you know when to stop using the site?

When I have my college tuition paid in full. Even then though, like if I could fuck a dude to pay for my rent, I’d do it. Whatever man, I’m a bad person, I know.


Jenna Homen is a contributing writer to Pacific Dissent and UpOut SF. You can view more of her work here or follow her on twitter