Testimonials from 2 Sugar Babies

Here are two emails I received from real life sugar babies explaining their lifestyle

Let me just brain dump a bunch of what I can share that might be relevant, bearing in mind that I'm not exactly your "typical" sugar baby (so I hear from dudes as well) but am insatiably curious about this and have had many conversations with these dates and other women over the years... 

1. There's a continuum between "pay for play"/"pay per meet" which I would pretty much call thinly veiled escorting, and "long term exclusive"/"marriage minded" and even non-sexual companion relationships (which is rare but not unheard of). Also, cash vs gifts/travel is a big dividing line. I've been operating sort of in the middle of the spectrum, where I'm happy to sleep with someone I feel a safe, genuine connection with who has long-term interests, and have spent a couple of meal/drinks dates with getting to know them, and as long as there are terms discussed up front. I've had perhaps 9-10 "arrangements" like this over the years, with 3-4 of them being one-time where we just mutually didn't click that well and never really followed up, and the rest lasting months to a year or more.
   
   I don't exactly advertise that I am pursuing multiple relationships, but I am truthful if asked. Non-monogamous to the core, as I've tried to openly be in relationships since I realized this as a teenager. FWIW, I'm divorced and generally had a steady nesting partner in life rather than casually dating... while very sexually open, I've had only about a dozen non-sugaring male sexual partners in my 37 years of life, so I guess this is approaching the same total at this point ;) I'd say the introduction of this relationship dynamic basically just speeds up intimacy and there's no dancing around expectations of the relationship. I know they are there because they have more money than time, and they know I am there because the inverse is true for me. They don't have time to go out on several dates with numerous women in order to get laid semi-regularly, or have been totally striking out for years. There's also a strong mentoring aspect to it. Lots of these men especially in the Bay Area are in tech or business or finance, and many of the women are looking for career guidance or industry connections perhaps even more than luxury gifts. Many men's ads say "no pros" and they want a genuinely loving relationship, not just a hookup. 
   
   
2. The line I have gotta hear more than anything else is "I love my wife, but..." As in, they're in their 30-60s and don't want to get divorced for whatever reason, but the intimacy/kink/etc isn't there in the way they'd like. One guy in his late 30s I saw for a long time said his wife approved of him having sex with women outside the marriage, but only if he paid for it (ostensibly to maintain emotional distance), which I found fascinating and not unheard of in the space since. They're more happily divorced now. My ex-husband was older than me and I've had a fairly substantial amount of life experience, and generally find dating older men more satisfying, so this has been a natural fit for me. Of course many guys are there because they want to date the hottest, youngest women so I am excluded from a lot of searches ;) Like you mentioned in your video, I worry that many of especially the younger women on there aren't fully aware of putting themselves in potentially risky situation. But really, is it more risky than a one night stand you meet in a bar? It's a different kind of risk, often out of desperation for cash or fancy things, and I think inexperienced women are probably more willing to go along with overriding their boundaries or spidey sense because of that. I worry that there are men particularly good at plying girls with drinks or using psychological strategies to move things forward, but again, I just hope we're all learning and being smart enough about it. 
   
   
3. The concept and website itself have had a LOT more press over the years (I'm comparing 2013-14 to 2019) and it's changed the tone significantly. I think more guys have been burned now by women demanding monthly allowances and then ghosting. There used to actually be dropdown fields for expected monthly allowance, for example, starting (I think) at <$500 and going up to $10k+. It's muddied the waters. If they haven't brought up anything related to "gifts" or some kind of "exchange" by the second date, I will usually try to. Unclear if he was attempting to be manipulative or genuinely clueless, but one guy I went out with a couple of months ago (breaking my own soft rule to not meet men only in town briefly for travel, because his background as a game theory professor intrigued me) was apparently surprised and slightly offended I was expecting some kind of compensation. It set an uncomfortable tone, so I ended the date.
   
   
4. Back in 2013-14, one of my ongoing arrangements was actually with someone I'd call a household name, and two were senior VP or C-level execs at public tech companies. Two of these three men I'd say would have a lot of difficulty dating "normally". They were interpersonally awkward, detached, and I bet have been burned by women taking advantage of them for the money, putting up with in one case a psychologically wounded narcissist (not in the aggressive sense, just in the "let me talk about career achievements and my parents approval and Important Things in my condo for hours every time we meet" sense) in his 60s. I think in these cases we'd rather have all our cards on the table, be clear about expectations and compensation, knowing both parties are enthusiastic and there's no pretense about what's happening.
   
   TBH, I'm not currently looking for a serious relationship right now, so my sweet spot is busy tech execs (because I like to talk tech/biz and have the background for it even if I'm trying to get out of the field) who are looking for someone smart, beautiful, and interesting they actually want to talk with over a luxurious dinner on a semi-regular basis, and know they'll get laid if they ask and "donate" accordingly ;) No more, no less. Yes, there's a lot of wink-wink type talk, usually in person, although I've known some guys who bring it up in chat. One guy I had a couple of dates with last month mentioned how he has a soft spot for helping out single moms. Some of these men do have a bit of a white knight complex, don't actually live that luxuriously, and a few hundred to a few thousand dollars a month towards their favorite extracurricular activity is no biggie. Some probably respond more to a sob story of needing money, and some are more into a woman with an established career and/or concrete goals.
   
   
5. An IRL friend of mine also did this for most of a year and had a VERY different approach. I'm much more of an introvert and concerned with establishing a connection/relationship before there's any plans of bedroom/hotel time. I'm just not comfortable otherwise and it doesn't feel genuine. However, she's a super extrovert, bold, scattered, and hyper-sexual being who has the energy of a freaking rabbit while trying to fund her startup, and happy to enjoy sleeping with most of the men she meets from the site, asking for money afterwards. She's much more concerned with their physical attractiveness and sexual satisfaction and doesn't get too disappointed when things don't pan out. I honestly care very little about that and am more interested in being relaxed and stimulating conversation. She's kind of more of the "I'll take what I get" type when it comes to money, but I treat mine like a business deal with the terms at least mentioned in advance. Not like I have much recourse if someone doesn't pay me, so a lot is operating on trust. Neither is "wrong" of course, but I found the contrast pretty striking. In ongoing relationships, I've made anywhere from $500 for a hotel meet plus fancy dinner, to $1800 for a couple hours at his place. Often guys want to do no condoms, but I treat this exactly as I would in terms of someone I met outside of Seeking -- not until there's trust and open discussion of test results :)
   
   
6. I love bringing this up in social situations if I feel comfortable. "What do you do?" "Oh I'm a sex worker" etc. I live in a unique community with a lot of openly sexual, progressive, Burning Man, etc type folks in San Francisco who may have been to orgies or play parties before, so my social situations may be a little skewed ;) But it's brought about some great conversations, including I'd say about 1/3 of women in their 20s-30s who when I mention being a sugar baby, say either "oh I've done that!" or "oh I've thought about doing that!". Sex work, sending nudes, etc is much more normalized in younger generations and the judgment is perhaps lessening, but still, I'm uncommonly open about it. However, I'd say it's split pretty evenly between women who would agree it's "sex work" and women who are more casually of the mentality that they want him to pay for all the expensive dates and some nice gifts or trips and don't consider it that kind of "work" at all. 
   
   
7. I'm trying to steer this brain dump back to what I think you and your audience might like to know... I agree that the widespread nature of it is probably the most surprising to some. Really though, for the majority of relationships, it's either a mask for straight up escorting services, or just codifying the kind of financially imbalanced relationship dynamic that has existed since the dawn of procreation. This "gig" has been strongly motivating for me to study psychology in greater depth and want to help people, because so many men seem to struggle with opening up and getting emotional support unless it is someone they are sleeping with. I feel like much of the value of what I do is in the supportive, you-focused pillow talk rather than the actual sex. But so many men are looking for a travel companion or even a future wife. Given my genuine compassion for connecting with truly awkward or lonely penguins, I consider it a high value service needed in the world and worth my price tag. 
   
   
8. Strategies for men? The better you are at reading the room and talking at the right level of explicitness vs read-between-the-lines, the easier this will be. I suspect a lot of men have an easier time (whether this is fooling themselves or not, I'll leave as an exercise for the reader...) "ordering a prostitute" through something like Seeking.com than other means. That being said, expect some potentially awkward situations and slightly mismatched expectations. Use your ad to hint at the kind of relationship you're expecting. When I see words like "allowance" and "X times per month", I get a clear expectation that they are comfortable with the transactional elements. But some women will be scared off if you start putting dollar amounts in messages or anything that has a whiff of being paid for sex. Really, it's just like any dating website, just with this additional element, and you'll get out of it what you put into it. It can be no less "real" in terms of relationship quality than meeting through any other means, if you're lucky! Meeting quickly is generally your best bet, even if it's just for coffee, because there's nothing like an in-person chemistry check and making sure the person you're drooling over in the ad matches reality. I get the impression that there's even MORE of a gap between some people's presentation of self and in-person self than in traditional dating. I've heard some horror stories, and it makes sense, since the stakes are higher and there's often more desperation at play. 
   
   
9.  It does suck that this is another way of emphasizing how the income gap and physical attractiveness separates what kind of relationship is attainable for both parties in life. I can hear the lament of men who think they don't have either the looks nor spare ~$1k+/month to think about approaching this kind of relationship. But I'm just happy there's another possible avenue out there, and trust me when I say that it's not a silver bullet to solve your life's problems, on either end. However, if you have the income and want more of a "low effort girlfriend" where the expectation is that you don't have to deal with much in the way of her emotional needs to keep the intimacy going ("no drama" is another line I see a lot in ads), it can be a great approach. Just read between the lines and be honest (with yourself, and each other) and smart and safe. Sugar babies are usually not smooth-talking pros. Just like any other dating site, there's usually many different types of people, and hopefully something for everyone. 

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 Alexander,

I watch your videos during my commute.  I recently caught your episode on Sugar Babies and I wanted to share some insights.  Please keep me anonymous, thank you.  (Explicitly: permission to use any of this is reliant on keeping me anonymous.)

My name is BLANK, and I was an American sugar-baby.  I can answer most of your questions honestly since very little has changed in the last few years.  (I still know girls in the lifestyle.)

I'm not doing a formal presentation so this is mostly stream-of-thought.  I do apologize if this makes my thoughts seem random, but sometimes they are.

I started my sugar life while I was attending university in a large American city.  Friends of mine were doing it and it seemed like a rewarding and fulfilling way to get validation and get someone else to handle some of the stresses and burdens in my life.

When I completed my degree work, I used my connections to acquire a reasonable starting position.  From that point onward, I dropped the sugar life and have earned everything since then.  I still meet up with some of my Daddies, for fun, but that's all there is to it.

Being a sugar baby isn't about being a prostitute in the typical definition.  It's about being my best self and using that to help someone else become a better, happier person. (Yes, I know how it sounds.  But at its core, that is what this is about.)

My first sugar daddy was a professor at my university.  I was never a student of his (to avoid any potential conflicts of interest).  He helped me by tutoring me and covering a few bills.  I provided him with some eye candy and open feedback - I always presented my best self around him, and I would tell him (very honestly) what modern students really thought about his 'banter' and 'humor' that he would add with his lectures.  (For fun, sometimes I'd study semi-nude, just to wind him up.  He was married so there was NOTHING done which would risk that marriage; not even a kiss on the cheek.)

I had other sugar daddy arrangements which did get sexual, but it was because I wanted to and not out of some obligation.  (...though friends have.)

You wanted to know about money, and I will address that shortly, but there are a few points which must be understood, first.  In prostitution, the rules and expectations are spelled out plainly and honestly.  In sugar life, there is a lot more nuance to the rules and expectations; it's a lot closer to "girlfriend of convenience" than "whore".

The understanding is that both people are providing services to each other, and neither is desperate or risking anything.  The sugar baby *could* be spending her time with a different Daddy while he *could* be spending his resources on a different Baby.  Neither one wants to be passed up, but both know there are other options.  It's about the convenience of everything.

There's so little emotional involvement but there is a degree of trust... to a point, of course.

The Daddy gets to flex his pride and show off his resources and brag and be the man he wants to be, but society or environment (work, usually) won't allow.

The Baby gets to feel beautiful and appreciated in a way that society and peers (and feminism) won't allow.

The sugar life feeds into something very primal and non-PC - but with a hint of class and without heading into caveman culture.

As for compensation, with some of my Daddies I was taken out to nice restaurants or given nice clothes with him getting to have the company of a smart, well-read companion who happens to be attractive.  (And in the case of clothing, jewelry, etc the Daddy gets to see it modeled for him... however he likes.)

For me, most of the Daddies would have the decency to remember I needed compensation and would ask if there's anything they can do to "help" me with something.  If I had a bill, debt, or other issue I would mention it and he'd take care of it.  (In one case, I mentioned my car payment was due and the Daddy paid off the remaining loan.)

In the cases of Lazy Daddies, I would mention (very casually, of course) something burdening me.  If he didn't take care of *something* or otherwise make my investment of time worthwhile, then I wouldn't make myself available to him.  Usually, they would get the hint and step up, or they stepped away.

It wasn't all roses and wine, of course.  Sometimes there was a distinct lack of chemistry and things didn't work out.  Or the guy was not interested in a mutually beneficial arrangement.  Those cases were typically resolved with everyone being mature.  (Not always, sadly.)

I hope this resolves some of your questions.  If you have further questions, ask and I will likely answer.  Please be aware that this is a junk email account and not checked very often.

PLEASE KEEP MY NAME AND OTHER INFO ANONYMOUS.  Thank you.