How a ‘Sugar Baby’ Does Money

The time Julia Roberts was a pretty woman prostitute

After my recent post about the “sugar baby / sugar daddy” phenomenon, a reader contacted me saying she would be happy to discuss her life as a sugar baby. (Anonymously.) Here is a record of our conversation.

Ester: Hello! How’s it going?

SB: I’m good! How are you?

Ester: I’m good, thanks! Without piercing the veil of anonymity, can you tell me / the readers a little about yourself?

SB: I’ll try! I do try to be pretty private about my sex work life and … the rest of my life. I’m 29, I work for non-profits, I have a master’s degree, I live not-in-New-York …

Ester: And you’ve had four “sugar daddies”?

SB: Yeah, I would say that I’ve had a sugar daddy pretty much straight for the past 5 years (but, actually, not right now!). I guess it works out to four more serious relationships. (‘relationships’?)

Ester: So maybe that’s a good segue in! How does a sugar-y relationship differ from a run-of-the-mill one? Is it more “50 Shades of Grey”-ish, with or without that contract he asks her to sign? Are you able to pursue romantic relationships on the side?

SB: Hahaha, no, I don’t feel like there is anything “50 Shades” about it, but I’m seeing it from the inside. The main differences in my sugar relationships: I’m dating much older men, I stay (even more) romantically reserved than I normally do, and there’s a clear arrangement with regards to money. I actually don’t know a single other person who claims to have sugar daddies, so I don’t know how other people see it, but I definitely see it as work. Work where it’s my job to make it seem like I’m not working at all.

Ester: That is fascinating and makes a lot of sense. BTW I should say up front that I know not-that-much about this and do not mean to offend, but I will probably mess up at some point, so feel free to tell me I’ve overstepped and put me in my place, okay?

SB: Oh my goodness, ok, well, I totally understand that you might not know a lot about this specifically but sure, I’ll let you know if I feel offended. (But I won’t put you in your place! People don’t have places!)

Ester: Hahaaha fair enough. And thank you. OK, so can you tell us how you got started with the first older gentleman?

SB: Sure. I was casually dating someone who told me about their ex-girlfriend who met up with a SD twice, didn’t have sex, and got some exorbitant amount of money. Even now, 5 years later, it seems like a lot of money for someone to give someone else on a second date. And this person I was dating told me that if they were more traditionally feminine-ly inclined, they would sign up for SD websites in a heartbeat. I was intrigued enough that I signed up. We broke up a couple weeks later, but the SDs have stuck.

Ester: How long after you signed up did you meet your first SD?

SB: Pretty soon! But he was fairly unpleasant, and we only saw each other for a couple of months. I wouldn’t say that I meet even 35% of the guys who message me, but of the guys I do meet, I have only ever seen 3 of them more than once. It’s like online dating, but I’m even pickier with SDs.

Ester: Did you have to design a profile for yourself? What did you say?

SB: I don’t want to sound like a brat here, but I basically said two lines about how I’m new to town and I like to experience life or some shit like that. I guess I figured being a blank slate is the best, well, the most neutral approach. (Interestingly, that is the exact opposite advice I give about online dating, so idk.)

Ester: Well, Ursula the Sea Witch did teach us that “the men up there don’t like a lot of blather.” Anyway, it seems like a savvy approach to the medium. How old were you, roughly, at this point? Were you in school?

SB: I was 24 (not roughly), and I was not in school. I already had my bachelor’s and was contemplating getting my master’s.

Ester: Were you in dire financial straits? Was this a straight-up thinking-with-your-wallet kind of decision, or were you intrigued for other reasons?

SB: I wasn’t in dire financial straits at all. I was looking for a job, and jobs in my field, in 2009, in that part of the country, were paying very little. But, no, it wasn’t dire. I have never thought of it as a replacement for a job. It would be the most incredibly nerve-wracking job I could imagine: you have one boss, and they can let you go without two weeks’ notice, at any point, for any reason. I feel lucky that I never had to rely on a single relationship with one other person in order to pay the bills.

Ester: How much time did it take up of your non-work week? Did it feel like a second job, albeit one with none of those benefits or protections?

SB: Well, it has always been work in my mind. It’s something I am doing in order to earn money. But it’s absolutely different than a ‘job.’ It has taken anywhere from 1 – 10 hours of my week, depending on the arrangement.

Ester: Was there an hourly rate, or how did the compensation part of things work? Direct deposit, cash on the nightstand … ?

SB: Something I see on a lot of men’s profiles is: ‘no pros.’ I think that what they are really asking for is to avoid the jarring feeling of transaction as much as possible. One thing that can help that is not having an hourly rate. I do, instead, have a ‘date rate.’ (I can see how that might be splitting hairs, but it feels different!) It’s also pretty common, though I have not done this, to have a monthly ‘allowance.’ The cash is usually in an envelope. Not to get smutty on the Billfold, but, really, sugar relationships are not solely about sex. Depending on who I was seeing, I would say that the majority of the time I spend with a SD, we are not having sex.

Ester: Smutty is what we live for! Don’t worry about it. So, what would the relationship entail? Being company at dinners, movies, parties, that kind of thing? Or someone to talk to? What were your responsibilities?

SB: I don’t know that I had responsibilities. And I hate parties. But yeah, we meet up for lunch and dinner a lot, go kayaking or swimming or to the beach or a play or a museum. And I’m someone to talk to!

Ester: That sounds so wholesome! Did you feel an emotional connection to the men? (Let’s talk about the men.) Who are they, these dudes who pay younger women to pay attention to them? Are they just lonely? Did they have wives?

SB: No. I don’t see people who are lying to their partners about what they are doing. I’ve talked to a couple people who do tell or involve their wives, but that has never worked out for me. The guys are single or divorced. They are lonely! They have all worked in jobs that appeared, to me, to be really flexible. They were their own bosses or had even, essentially, retired (but weren’t over 65) but continued to work in some limited capacity. My first SD told me that he dated younger women because they weren’t ‘cynical.’ Except, I suspect it is men like him who encouraged the cynicism in the women he has come across.

Ester: Ha. Good point. What were you like when you were hanging out? Mostly yourself? A more “pleasant” version of yourself? Did you voice opinions or just agree with his? Did that vary with the man?

SB: Sugaring is a long game (I don’t know what other phrase to use!) I could NOT pretend to not have opinions for a year and a half. Definitely, I was more agreeable, more pleasant. If I felt like I was ranting about something, I would maybe try to cut myself off. I probably didn’t go into details of my yeast infection. Since I got to pick who I dated, I really only ended up seeing people with somewhat similar political views, because even on a first date, you get hints of what someone thinks, and I think I probably come across as way less charming if you are a Libertarian.

Ester: Although who knows! Some people really like hate-sex, which is the only kind I could have with a Libertarian, myself. But yeah, it makes sense to think of it as a long game. How long did these arrangements last, and how did they end?

SB: Other than the first one, they’ve all lasted over a year, but never made it to two. They’ve ended because the arrangement didn’t make sense anymore: they didn’t want to keep paying for dating, they wanted a girlfriend who spent the night, etc. I think it’s the kind of thing that can only be fun for so long.

Ester: Was it ever fun for you? I mean, I understand it was also work, you were doing it for money, but were there moments when compartmentalizing became difficult and you began feeling romantic? Maybe that’s a stupid question. I guess a lot depends on whether you were ever attracted to the dudes in question.

SB: Yes, absolutely, it was a lot of fun for me. I did a lot of things I wouldn’t have done if I hadn’t been with these people, I had some really great experiences. And I had real affection for some of them. I learned a lot from them. Some, after the end of the relationship, I feel pretty bitter about. I wasn’t trying to not have romantic feelings at all, it wasn’t something that I was compartmentalizing, it just wasn’t there. It’s so hard to explain this!

Ester: Could you say more about the bitterness part?

SB: Oh, just like in any break-up, the circumstances around how it ended colored my thoughts of them. One SD was very … connected to me, and resisted me trying to end it. He tried to push my boundaries around privacy and ended up withholding money to try and get me to do what he was asking.

Ester: Ugh ugh ugh. Did you have any recourse at that point?

SB: Hell no. I just got out. He still creepily texts me on my birthday or on Christmas, but I just ignore him.

Ester: I’m sorry. Gross. Did you have other creepy / unpleasant experiences doing this through the site, or were the other exchanges largely okay? How would you characterize the experiences overall?

SB: I mean, I certainly got weird messages, and I did meet up with a couple of people where it was immediately apparent we were not going to get along. But I just left early and never contacted them again. I think that, overall, this has HUGELY impacted my life in a positive way. But I certainly wouldn’t recommend it.

Ester: Interesting! Why not?

SB: I guess because … it’s not easy? It affects that way I see men, relationships, age. I know it’s silly but, while I don’t worry about my own safety, I worry about the safety of other people. I wouldn’t tell someone not to do it, maybe, but I wouldn’t promote it.

Ester: Do you feel like you were qualified for it in ways that not everyone might be?

SB:  I wouldn’t want to say that I’m qualified in ways others might not be. I guess I just feel somewhat protective. If someone asked me how to do it, I would try to talk to them about what I did, and my experiences.

Ester: What are your plans for continuing to do it in the future? Is it hard to focus on having a romantic partner of your own while also doing this work? Of course I know that’s not everyone’s goal, but you mentioned online dating.

SB: Oh, not at all! I have a romantic partner!

Ester: Okay! So does that affect your decision to carry on with the SB thing? Does your significant other know?

SB:  My SO knows about SDs!! They are very supportive of my decisions.

Ester: That’s awesome. I could understand someone being “protective” (yuck) or competitive, so I’m glad you found someone who’s neither. So yeah, going forward, what’s your plan?

SB: I’m not sure! Having an SD makes a lot of things easier, but I’ve been dreading getting back out there and looking for someone. So, for now, I guess I’m just going to wait and see if I feel like it.

Ester: Can I ask if this has affected the way you see women and relationships? You mentioned that it has colored the way you see men on some level, and I get that, but do you feel like you’ve merely regularized / made official an arrangement that lots of women are in?

SB: No, I don’t think it has affected the way I see women and relationships. I mean, women have systemically been denied access to power, security, and wealth for, you know, basically all of time. Historically, teaming up with a man was one of their only chances at any access (however limited) to that power. I don’t see anything wrong with individual women doing whatever* they think is best for them in order to feel secure. One of you all even posted something last week about how the history of engagement rings had to do with, essentially, promising a woman something of monetary worth in exchange for their ‘purity.’ This feels, somewhat, like another avenue to that same conclusion, but I don’t think there’s anything superior or better about which road someone takes. I appreciate clear boundaries and expectations, and sugaring gives me that. That being said, I have never normal-dated someone who was wealthy, and I don’t really know how I would respond to that.

* I mean, I suppose that this has limits, like when it’s hurting other people

Ester: And what about your actual father? Does he know about this / have Feelings about it?

SB: I sincerely don’t think this has anything to do with my father. He does NOT know, and neither does anyone else in my family, and I hope to keep it that way forever and ever. You mean because I’m dating older men, right? I think those just happen to be the people who seek out sugar babies.

Ester: Not simply because of the older men thing but because they’re called “daddies.” That adds a potentially complicated layer to the situation, doesn’t it? Or am I overthinking?

SB: Ohhh. The word “daddy” sort of creeps me out, and my SDs never actually refer to themselves as “daddy.” More common: benefactor, friend, boyfriend. Even when I read “SD,” I hear ess-dee in my head.

Ester: Makes total sense. It tends to creep me out too even when people in ordinary couples call each other “mama” or “daddy,” like Marilyn Monroe does in Gentlemen Prefer Blondes, one of the best movies ever. But I understand that it can be a cultural thing. Anyway, thank you so much for chatting with me about this! Any last thoughts, things you want to add? I’m sure people will want to know how much money you’ve made in total and whether it’s reported income, if you’re comfortable disclosing that.

SB: I was wondering when you were going to ask! I haven’t always kept great records, so I’m not entirely sure how much I’ve made in 5 years, but I think I made about $12,000 this year and maybe twice that last year. It does get reported for tax purposes.

Ester: Nice. Considering a good percentage of the dudes must be in finance, they probably owe it to you to help you with taxes, too. Anyway, so, last thoughts? Anything you want to add?

SB: Well, I originally wrote to you, offering to talk about sugaring, because someone commented on an article you had posted that they wondered what it was like to go back to regular relationships after having a sugar relationship. It bothered me, you know, like suggesting that people who have cooked food for money will never again be able to cook food for people they love. I hope this has explained some of that.

Ester: I hope so too, but if people are still confused, maybe we can do it again sometime! It’s been fun chatting with you — thank you for your time. :)

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