Seeking Arrangements

 

Peter McGraw kicks off a short series that further investigates unconventional relationships. In this episode, he invites a sugar baby into the studio to talk about a not-so-new but increasingly popular type of relationship: an arrangement between a “sugar baby” and a “sugar daddy” or “sugar mommy.” The episode is launched without judgment. To McGraw, as long as there is consent and no harm is being done, people should be free to choose the relationship that is right for them. See the Relationship Anarchy episode for a primer in this respect. McGraw, his co-host, and guest discuss the history of “sugaring,” motivations of each participant, and best practices.

Listen to Episode #103 here:

Seeking Arrangements

Welcome back. We’re here to talk about a not-so-new but increasingly popular type of relationship. It’s an arrangement between a sugar baby and a sugar daddy or sugar mama. The episode kicks off a short series that investigates unconventional relationships. I don’t expect this series to be the final say on the topic. There are too many ways to diverge from the relationship escalator, but I hope you enjoy the sampling nonetheless. I want to be clear about something. I believe that being a loner, getting married, or having an unconventional relationship is good. What makes it good is that important part, and that is that you’re happy walking the path that you choose.

In this episode, we talk to a sugar baby, for our purposes, goes by the name Billy. Billy studied Apparel Merchandising at university. She loves fashion, travel, pop culture, veganism, weightlifting, and Kim Kardashian is her hero. The other part of we is my guest cohost, a familiar voice, Julie Nirvelli. Julie was born and raised in San Jose, California, and earned her college degree from Cal Poly, San Luis Obispo. She has lived in Colorado for seventeen plus years and is a strong, independent, and fun-loving person. Julie embraces her solo life. She also happens to be a sponsor of the show with their company, Bachelor Girl Productions, which offers you fun, flirty t-shirts.

You may be happy to know that bonus material is back and available to the Solo community. You can sign up at PeterMcGraw.org/Solo. If you tune into the bonus material on the Slack channel, you can hear a story about one of my dates who turned out to be a sugar baby to a married sugar daddy who had permission from his wife. It’s an interesting story. As always, please rate, review, subscribe, tell friends, family, and all that stuff. It really helps the show. Speaking of which, I hope you enjoy this episode. It’s a fascinating one. Let’s get started.

Welcome, Billy.

How are you?

I’m good. I’m so excited to be here. Before I introduce my cohost, I want my audience to know that I did a lot of research for this episode. Not in the field research, but research including interviewing a friend of mine. I’m going to call her Carrie to protect her identity. She’s part of the lifestyle community here in Denver, as she calls it, which includes performers, members of the kink community, and so on. She has experience as a sugar baby and is someone who has mentored several sugar babies. I invited her to come on as an expert, but she politely declined, so we’re stuck here with Julie, our less experienced cohost. Welcome, Julie.

Thank you.

I don’t mean that in a pejorative way. People who tune in to the show regularly know Julie and like her. We’re going to jump right in here, Billy, and have you tell us a little bit about your experience as a sugar baby. Why don’t we start with how it started?

I started my first year of college when I was eighteen. I had always liked older men, so my friends told me about this SeekingArrangement website. That is when I signed up. The first time I had an interaction with someone, it was a sexting type of phone call.

Is it like old-school phone sex?

Yeah. I was still a virgin, so I didn’t know what to say. I was really nervous.

Are you now 25-ish?

Yes.

You have some years under your belt now.

Is that something that you were compensated for or did you do it because you wanted to or was it a new experience for you? For you, what was the draw of that your first experience?

I did get compensated for it, but I was nervous to meet someone still. This guy wasn’t even in the same country as me. I was in England, and he was in Ireland. We weren’t going to meet regardless, so I felt safer dipping my toes.

That makes sense.

I didn’t meet anyone until I was nineteen, so it was a year later.

What did that look like?

I saw that guy for about six months. He owned a restaurant, so I would go there with my friends and we would have really nice dinners together, and then usually, I would go back to his house afterward. He also gave me a monthly allowance.

If people are reading this now and they’re like, “What the hell is going on?” all of this will start to make more sense. We’re going to get to know Billy a little bit here, and then we’re going to spend some time step-by-step exploring the elements of this sugaring, seeking arrangement style relationship. You progressed from these phone calls to having a regular relationship. You said six months it lasted. Are you still doing this?

Yes.

What would be the ideal relationships? I assume you can have more than one.

You can.

Did you?

No. Most guys don’t want you having more than one, because it’s a turnoff if it seems like it’s a professional job you’re pursuing. I don’t have multiple ones unless they’re specifically like, “I don’t care if you’re seeing other people,” but I always do it openly, so maybe I’m not having multiple sugar daddies but I can still go on dates or meet someone at a bar that’s not them.

You can have multiple relationships, but not multiple sugar relationships. That makes sense. Do you have one right now?

I do.

Is it ideal?

No.

Let’s do this. Julie knows exactly what I’m about to ask. What is it like now and what would be ideal, and how do we get this guy on the phone and tell him to step up his game?

I can’t do that.

What’s happening now and what would be ideal?

I met this guy in 2020 in July when I was in Singapore. I was about to move back to the States. I told him, “I’ll meet you, but I’m not going to be here much longer,” and he was like, “I go to the States a lot for business, so it’s not that big of a deal if we like each other.” I was like, “Okay.” We went to dinner and it went well, so he was like, “How does an arrangement sound? I’ll give you a $1,000 a month. When I come to the US for business, I will see you.” I was like, “Okay. That’s $1,000 a month but I probably won’t see you again?”

This is like a retainer. It’s like I have a lawyer on retainer that you’d pay. I don’t, but people do.

That happened for a few months, but then it was during prime COVID. He got really anxious and blocked me, because he was like, “I don’t know when I’m going to see you again. I can’t deal with this right now.” Chinese New Year happened in January 2021, and he randomly sent me $1,000. I was like, “That’s weird.” We pretended that it never happened that he blocked me. I’ve seen him three times since January 2022.

I assume there’s typically texting, phone calls, or some connection in between.

Just texting.

I’m getting that you’re not big into the phone call.

Yeah. A normal phone call is fine, but I’m not good at sexting or anything like that.

Why isn’t it ideal?

It’s not ideal because $1,000 is low, knowing how rich he is.

Are you off the market for other arrangements?

We’ve never discussed it. He’d get really jealous. It’s a don’t ask, don’t tell situation. I did see him on the website again. My profile is hidden, and I was like, “He’s on it,” so I blocked him.

Is that so he won’t see you?

Yeah.

This is already fascinating.

I agree.

What’s ideal?

Ideally, between $2,000 to $3,000 a month is better. With someone you see once a week or every other week, that would be more ideal, and something more fun things like gifts and trips. He sends me the $1,000 and that’s it. We go on dates when he’s here, but he has been here three times since January 2021.

It sounds like you want a little bit more of an experience, like going out for fine dining or going to Vegas for a weekend.

That’s more the ideal situation.

There’s more fun and excitement in addition to the payment.

He’s nice. I like him.

I hope so.

My next question was going towards something in that realm. When you said ideal is seeing somebody once a week-ish, and financially, the $1,000 a month for once a quarter or whatever is a better financial arrangement, so that made me think of my question, for seeing somebody once a week-ish, your goal is to really like that person and look forward to seeing them, and then this financial side of it is a little bonus.

That’s how I see it. It is really nice getting $1,000 a month through basically texting someone. I’m not going to give that up, but when he is here, we’ll go on dates and he will talk the whole time. He doesn’t ask me a single question. I’m like a diary, but instead of writing it down, he texts me whatever he’s thinking, and I go, “Yeah. Cool. That’s crazy,” and that’s good enough for him. We don’t have real conversations.

This is maybe a perfect segue into the nuts and bolts of these arrangements. This is enough to get people a flavor of where you’re at right now. We’re going to get into the why do people do this, and we might’ve hit on one of those things. I want to do a quick history lesson. At least, this is my perspective on this. One of the things about these sugaring arrangements is they sit in between this heteronormative, chivalrous dating situation where the guy pays and he’s trying to impress, and the woman’s interest in him is not completely contingent on this courtship where she’s going to want to like him for who he is and so on.

Let’s be honest. If he doesn’t pay for the meal, it’s not going anywhere. That’s on one end of the continuum. On the other one, it’s pure sex work. That’s the oldest profession, which is prostitution. You pay someone and they have sex with you. This sits in between, because there are elements of both that are there.

There is an interesting thing there. There are two meanings when it comes to the daddy part of sugar daddy, and this evidently causes some problems here and there. There’s this sugar daddy as in seeking arrangements. This gentleman in Singapore is a sugar daddy to Billy, but then there’s also this daddy experience that’s more of a kink where age play is there. They may co-occur or they may be separate, and I think they’re typically separate. Does that sound right, Billy?

Yeah.

This is not a new phenomenon. This type of arrangement goes back centuries. It goes all the way back to what was called the royal mistresses of a king’s court who received a yearly allowance. It goes back at least to the 1500s. This is not a new phenomenon, although it has certainly risen in prominence, especially because of technology. I had to look this up. The term sugar daddy didn’t appear until the early 1900s. Allegedly, Adolph Spreckels, who was the heir to a sugar fortune, was affectionately referred to as sugar daddy by his wife, Alma. Guess how much younger Alma was than Adolph? It was 24 years, so there was a little bit of that dynamic there.

In 1926, sugar daddy had become a well-known slang term for a man who spoils younger female companions with gifts, money, or both. This was especially the case with the flappers in the roaring 1920s. This is where it gets funny. In 1925, a chocolate salesman created a caramel lollipop named the Papa Sucker. In 1932, they changed the name to the Sugar Daddy, which is less gross. In 1935, they came out with an accompanying candy called the Sugar Baby. The concept was brought to more prominence in the ‘50s with Hollywood films such as How to Marry a Millionaire and Gentlemen Prefer Blondes both starring Marilyn Monroe.

Perhaps the most famous sugar baby, at least in my eyes, is not Billy, but it’s Holly Golightly of the movie Breakfast at Tiffany’s played by the charming and stylish, Audrey Hepburn. Instead of calling the bad sugar daddies trolls like they’re called these days, she called them rats. The growth of this happened via this website app that Billy mentioned earlier, SeekingArrangement, which launched in 2006. I have to ask you this, Billy, because you had mentioned this to me. The founder of the app is prominently featured on the app, yes?

Yes.

What’s the story there?

His name is Brandon. You can see his profile. It has a little crown by it, and it says founder. He uses it for dating. He has multiple sugar babies, but he also is like, “If I vibe with you and we get along, maybe I can hire you for something else.” He is into petite, slim, and small women because he’s shorter himself.

Let’s talk through this since we’re already on the app. Do you create a profile much like a dating app profile?

There’s a question like describe yourself, and then there’s a what are you looking for. I write more of a paragraph for each of them. On a dating profile, I don’t write anything.

You’re trying harder on the SeekingArrangement than you are on a dating profile. Do you have pictures on there?

You can have public pictures or private photos.

What does that mean?

A lot of people would have a photo like their face blurred out, and then you can share your photos of someone else or you can have everything public. Usually, they’re not sexual photos. They’re just people wanting to be private.

Do the sugar daddies and sugar mamas pay to be on the app and then the babies are free? How does that work?

I know the sugar daddies have to pay. I don’t know if the sugar mommies have to pay.

Is it sugar mommies or sugar mamas?

I don’t like the word mama, so I’m not going to say that.

That’s fine. I don’t know the lingo.

I don’t know if they have to pay or not, but I don’t see the mamas or mommies come up.

It’s because you don’t have yourself as bisexual on there. Here’s my guess. Knowing the apps, you can pay for extra features. It’s a freemium model or much of it is free, but if you want to be able to see who has looked at you or who has liked you, you might pay extra.

You have to pay to message people. You can look at people’s profiles, but you can’t send any messages.

I get it. It’s like looking at a menu, but if you want to order something, you got to pay. That’s great. Let’s talk about who does this or who are the kinds of people on there. There are males and females, straight and gay, but prominently, it’s usually older men and younger women. That’s typically the case, but it may be older men, younger men, older women, younger women. All quadrants are connecting.

There are also other rich women wanting to date rich men, so some people don’t really use it for a sugar baby. They’re just wanting to connect with rich people in general, and it’s a way to find it.

Let’s talk about these clients. Let’s call them clients. I’m not sure that’s exactly the right word.

What word would you use? We’re trying to be educated on the lingo.

I say clients because that’s what Carrie calls them. What would you call them? Do you just call them sugar daddies?

Yeah.

Typically, they’re of means. They have money.

They should.

I’m so glad you said that because, and this is according to Carrie, some guys don’t.

They’re posers.

They’re called Splenda daddies.

They are living beyond their means or they’re faking it. Tell us everything. Tell us what’s going on.

What’s going on with them?

Yeah. Who are these guys? What are they doing? How are they different than an ideal client?

You can see their networks and their income. If I see someone with an income of $500,000, I’m like, “I don’t know why you’re on the site,” but then you have to take into account if they are married and do they have kids, because if you’re just single, then that might be more money, but if you have three kids and eventually have to pay for college, you need to have more money than that to be a sugar daddy.

It’s so interesting that you say this because a sizable minority are married, and they may be married and out there in the open. I’m going to have a story I’m going to tell you. It’s going to be in the bonus material about one of these arrangements that I’ve learned about from a woman I met on the apps. For those of you who are curious about this, it’s my only other sugar baby friend besides Billy. If you’re interested in this story, you have to sign up for the Solo Community at PeterMcGraw.org/Solo.

Here’s a preview. In her case, the man was married, but his wife gave him permission. She knew that he had sought an arrangement that was there. There are married men who are either cheating or have permission that’s there, but regardless if they have a wife and kids, they better have more money. That’s what I hear you’re saying.

Do they disclose all of this in their profile?

Yeah. They have a section where you can put your relationship status. You can also put there if you have kids, and what your occupation or industry is. It’s all in that section.

None of this is checked, so when someone says their income is $500,000, you won’t know for sure.

There’s no way to check it.

I have been pretty good though, at being able to tell from a photo if someone’s rich or not.

I’m wondering, how poor do I look?

You don’t look poor. You can tell by the shoes and how old a photo is because they could have really cool photos but I’m like, “It looks like your outfits are Abercrombie and Fitch in the 2000s, so that’s clearly not an updated photo.” Red dress suits or red dress shirts, rich guys don’t wear those.

Some of it’s about taste. You’re figuring out someone’s income via how tasteful their photos are. You’re seeking clues. You’re trying to figure out who’s sugar and who’s Splenda.

Especially the mirror selfies. If you took a photo in your bathroom, I could go, “He has a nice apartment,” but I can tell some people, I’m like, “That is not a nice bathroom,” so I’d be like, “You clearly don’t have a nice apartment.”

You’re sleuthing. That makes sense.

If the door is closed in a bathroom selfie, then they’re hiding taking a bathroom selfie from the person they’re in a relationship with.

I’ve never heard this before. That’s funny. Clearly, I don’t live with anyone, so I don’t have to worry about this. The people who do this, as we said, tend to be men. They tend to be higher income, but not necessarily. There are women who do it, and then also, there are guys who don’t have as much money but appear as if they do. Maybe in the same way that they’re living on credit, they’re appearing to be something rather than they are, so they get to spend time with the lovely Billy here. Why are the daddies and mommies doing this stuff? That sounds like an obvious question, but I don’t think it’s as obvious.

I would say the most common thing is they are busy people. They have really busy jobs and they’re traveling a lot. It’s easier because you’re paying for a girlfriend in a way and she doesn’t cause drama. We would be like, “I’m not going to be mad you didn’t text me for three days in a row.” It’s convenient.

It’s low stress. I could see that. What else? Are they any other reasons?

They’re married and they’re miserable is another big one.

They’re looking for some excitement. They’re looking for sex, because they maybe not getting that at home perhaps. Carrie gave me a whole list, so I’m working our way through this.

There are a lot of husbands and wives on there. I’ve been with a couple. The wife figured out she was bisexual after three kids and married, and he was like, “Let’s figure this out for you then.”

It’s like they’re looking for a unicorn. For those of you who don’t know this, a unicorn is the third in a threesome with a couple.

Instead of going on Tinder and fathering lesbians, they’re like, “I’m going to get on SeekingArrangement and pay someone to do this.”

It’s less threatening to the relationship because you’re creating an arrangement. That was not on my list, by the way, although fantasy fulfillment was.

Is it a roleplay thing?

Yeah. You’re looking for a particular type of person.

There are people with kinks on there. I’m not good with roleplaying, so I stay away from that.

We know you’re terrible at phone sex.

I’m pretty quiet. You can’t ask me to narrate a story during sex either, so I don’t really meet those people.

You get filtered out.

In the unicorn situation, is that a regular occurrence where you have that retainer situation again?

When I was with the couple, we were together for four months, but sometimes, I would just see the husband, and the wife knew. She was like, “We couldn’t get a babysitter tonight,” so she had to stay home, but they were fun.

What brought that to a conclusion?

He had to get surgery on his shoulder, so he was like, “I’m going to be out of work, so I won’t be making as much money.” It was like a sales-based job.

Real life gets in the way sometimes.

They were really nice. If they canceled last minute, they’d still pay me. That’s why the husband would go if she couldn’t go because they felt bad being like, “We’re sorry. We don’t want to take away your money.”

Another one in this, which you already alluded to with your current situation, is for someone to listen to, some companionship, or a girlfriend experience where someone could go, “That sounds very difficult.”

Some people or guys just want to vent and have someone there to listen to them, but they have no desire to be in a relationship or committed.

It’s a little bit more one way in that sense. Julie and I are friends. I have to listen to her, and she has to listen to me. If it only went one way, the friendship wouldn’t last very long. This is going to sound a little crass, but this thing of a guaranteed outcome or a predictable like, “I want to have sex.”

You’re not wasting your time taking someone out to dinner.

Also, waiting and hoping that maybe they’ll say yes at the end of the night.

The best sugar daddies don’t expect sex. The allowance is sent to you regardless of whether they see you or not. That’s not how most of them are, especially depending on where you live, but I would say a true sugar daddy is someone who sends you your weekly or monthly allowance. Even if you’re busy or they are busy, it doesn’t matter whose fault it is, you’re still getting the allowance, but it’s guaranteed sex.

It’s not fully. When we talk about this continuum from this heteronormative chivalrous courtship thing, it feels transactional, but it’s not articulated to pure sex work prostitution, which is pay to play so to speak. This sits in between where there seems like there are some elements of both at play that’s there.

With the married couple, would you guys go out and do stuff together, or is it more nighttime at home?

They were super into eating. They would order ten appetizers and three entrees, so we’d go out for these ginormous meals.

I’m surprised they didn’t fall asleep having sex afterward.

We did that before. I don’t know why.

Do you have sex first?

Yes.

That’s interesting.

They were super fit, so they were like, “This is our one cheat meal.” We usually would do shrooms too, so that was a bonus that I got shrooms.

That’s fine. I always think of shrooms as suppressing your appetite, but nonetheless.

How old were they?

The guy was 42 and his wife was maybe 38.

These are the motivations of the daddies and mommies. It’s the fantasy fulfillment, kink, convenience, some guaranteed outcome, this girlfriend experience, someone to listen, and maybe to help make up for a current relationship that’s not satisfying. Some or all of those are there. Let’s talk about the babies. What are your motivations?

I like older men, so for me, if I’m going to date anyone, I’m going to expect them to pay. I’m not a girl who’s ever going to do 50/50. I was like, “Why not date rich men? If I’m going to date them, why not get paid to do it?” For me, I would do it regardless about money, but why not?

Why not get the extra bonus?

Exactly.

I remember we had a conversation previous to this, and you said something to me that Carrie talked about also. I was like, “What are the motivations?” She said, “A lot of sugar babies don’t want to work.” They don’t want a full-time job or maybe they have a job that’s not traditional that gives them a lot of flexibility like they’re a performer or something like that. Does that ring a bell?

Yeah. Ideally, I don’t want to work, but I wouldn’t say it’s my motivation because I still want a job.

It’s a bonus.

If you go on that site and you’re like, “I’m unemployed,” it’s a major turnoff. It’s a lot harder to meet someone, because if you say you’re a student and you’re trying to go through college, they’re like, “I have to help you.” They feel like they’re saving your life, so they’re not interested in unemployed people.

That’s because the motivations are wrong.

They feel like you’re just doing it for money.

That’s so fascinating. Carrie described the money as easy-ish relative to a lot of traditional work.

It can be easy if you like the person you are with.

If you don’t like the person, then what?

I dated a guy for six months that I did not like at all, but it was during COVID and I was being safe. I didn’t want to go meet a bunch of people.

It’s loving the one you’re with.

It was that situation.

Did you eventually end that one?

Yeah, we dated for six months, but that was hard.

Are you a good actress or did he know this and not care? When I go out with people, I’m super sensitive when someone is not that into me.

I don’t know. What was really bad was the sex. He made the comment, “It’s like having sex with a virgin every time with you,” because I just laid there.

Did he like that?

I don’t know. I’d have to wear a blindfold because he didn’t want me looking at him. It was really weird. I had to see him twice a week.

That’s a lot for somebody you don’t like.

I know, and one night had to be a sleepover.

Is that cuddling and other stuff?

Yeah, but I was like, “Don’t touch me. I don’t like cuddling.”

What you described seems like work.

It honestly felt like a job.

You’re like, “Tuesday night is sleep overnight.”

That’s what happened. I was dreading it every time I went to go see him.

Was the money good?

Yeah. It was $500 a week, which is pretty good. Two times is a little much, but I was also unemployed and had nothing to do. We’d always go out to nice restaurants.

The first time you met him, were you like, “I don’t like him that much, but I don’t have a lot of other options right now because of COVID,” or did that build over time or were you hoping it would get better? I’m really curious.

I met him and another guy at the same time period. I was hoping the other guy would choose me, but that guy was like, “You look so young. I feel like I’m with my daughter. I can’t be with you.”

We’re keeping Billy’s identity a secret for safety reasons, but Billy looks young. For some people who want that age play, it’d be great. You could pass for twenty years old if you wanted to.

This guy’s like, “You look fourteen. I really like you, but I can’t be with you like that.” I chose the other guy out of convenience. In Colorado, I don’t have that much luck with guys here. They’re a little too outdoorsy for me, so it’s hard finding guys who are interested in more city-type things.

That’s right, like urban living, dining, museums, concerts, theater, or travel.

The guy that I was with was more into that. He dressed nice and liked nicer things.

Is he a nice person?

No, but that didn’t come out until later. It’s not like I was like, “He’s awful. I’m going to date him.” As we got closer, I was like, “I can’t believe he’s saying certain things that he said.”

Let’s keep moving. Are there any other reasons why the babies do it?

Some girls do it to purely scam men. They have no intention of meeting them. They’re just going to try to get money before or they’ll try to go on a dinner date with you and they’ll be like, “You need to give me money for gas.” There are some girls who are doing it because they’re trying to get quick money and they think that they can take advantage of guys easily.

There are scammers on both sides of the relationship. Do these babies have a name?

I don’t know if they have a specific name.

Splenda babies.

I was wondering what they are. Carrie only added one other one, and she said that it’s fun, exciting, and sexy. It has this fantasy fulfillment on the other side of it all.

It does feel nice when you leave someone’s house and you have $1,000 in your purse. You feel very powerful afterward.

It’s fascinating. I can see how both people feel that way. There is the power to be able to pay and to have this no strings attached situation, and then the power of like, “I did that.” I like to say this for folks who are pro-choice. If you’re pro-choice, it should extend into sex work. If you believe that a woman should have autonomy and power over what she does with her body, it should go to the ends of supporting sex work, because that’s a similar dynamic. You’re doing what you want and how you want with your body at the price you want and so on.

You also would get to go to restaurants you would never get to go to on regular dates, and these potential travels and all the experiences that regular dating wouldn’t necessarily provide.

Also, shopping.

I love shopping.

This is something that came up that I did not realize. Let’s talk about the hows that are here. It’s not just SeekingArrangement. There are a whole bunch of apps that people use for this, but that’s the big daddy if I may. Are you on any other apps?

I tried SugarDaddyMeet. I don’t like it. SeekingArrangement is the good one. I’m on MillionaireMatch, but that’s just a dating website. It’s supposed to be for rich men.

The other one, and I know this because I’m on the regular dating apps, is that there are sugar daddies, sugar mommies, and sugar babies on the regular dating apps using the app in a way it wasn’t necessarily intended to. There is a lot of coded languages. I can only talk about the babies’ coded language because sadly, I’m too old to have a sugar mommy at this point, but correct me if I’m wrong.

I want to know so I can put this on my profile.

You’re on the dating regular dating apps too. You’re regularly dating, but you might use them for crossover. Spoiled is the big one. Anybody who’s looking to be spoiled is one of them. I also think this idea of saying that you like shopping is another one that’s coded language. After that, maybe fine dining. Versus saying I’m a foodie, saying fine dining feels a little coded to me, but certainly it’s the first two.

My bio used to be, “Spoil me.”

Is there anything else that you might do on a regular dating app to signal that you might seek an arrangement?

I don’t know. I’ve thought about this.

You’re trying to hack the system.

SeekingArrangement is going down, so I need to move to dating apps, but it’s awkward when someone messages you and they’re like, “What does spoil me mean?” I’m like, “I don’t want to explain this to you.”

If you have to explain it, they’re not a good client.

If you have to ask, you can’t afford it. You can say that.

What about communicating? You communicate in-app, but then once you go off the app, how do you do it?

I use my real phone number. A lot of people use Google number or whatever it’s called.

How about Snapchat?

If it’s Snapchat, they’re either usually someone who’s a schemer like they’re trying to get your bank information or they’re someone who’s married. I’ve noticed this from people who use Snapchat, but most people don’t ask me for my Snapchat.

There’s also, and I’m not familiar with this, but another app called Kik.

I do get asked if I have Kik, but I don’t like apps, so I’m not going to download an app to talk to someone. Also, that’s an old app. I don’t know why they’re using it still. There are other things to use like Telegram.

From my understanding, the value of Snapchat is the messages are impermanent, so they go away. There’s not a lasting record of this. Also, if you take a picture of the communication, the person who sent the message is alerted to it, so now you know if someone’s trying to troll you. It creates a higher level of privacy with these. Kik must have that thing. That’s a little more popular with sex workers. That’s my understanding. For example, in Carrie’s rules, she has like, “Don’t snap my pictures without permission.” She also has other rules. Do you have any rules when it comes to meeting, how do you communicate and get things going?

I try to get their phone number out of convenience because it’s annoying to log on and talk to them. I don’t feel the need to ask for more photos, but a lot of guys are like, “Can you send me more photos?” I’m like, “I already put my really great ones on the site, so I’d have to find more.” I don’t do coffee dates.

Is it a meet for a meal or for a drink?

I don’t do drinks.

It needs to be a meal.

A dinner or lunch is my requirement, and it needs to be in public. A lot of people are like, “Do you want to come over to my house?”

That seems crazy to me.

I know. That happens on regular dating apps too.

I’m amazed when people do that.

Do you want it to be a meal because you want to know that they’ll invest or do you want that amount of time with them? I’m the opposite. I don’t want to commit to a two-hour dinner if I don’t like dating the person.

For me, coffee, in my opinion, I buy myself coffee every day, so I don’t need someone to buy me coffee. A drink seems like you’re just trying to get the date over with quickly so we can go back to your house. A dinner seems more like you’re invested in actually getting to know me. It seems not like a hookup situation.

I like that. That makes sense.

It’s so interesting, because for me when I go on date dates, I want to do coffee or a drink. My friend, Matt, calls it a face check. He’s like, “Make sure the person looks like their photos and see if you vibe,” so coffee or a drink seems like the right thing to do, but for this, I can see why it’s the wrong strategy because it sends the wrong message.

A lot of guys do try to do a coffee or drink date.

That’s a rule that you have. Do you have any other rules?

It has to be a nice restaurant.

You’re not going to Mongolian barbecue.

Someone invited me to Spaghetti Factory once. I was like, “I’m sorry. I can’t meet you anymore.”

That makes sense. She had of couple others. Carrie was like, “Don’t pester me. I don’t want lots of texting. We make plans, we meet, but in between, we don’t have to be communicating all the time.” Here’s another one. Money up front, and that’s once the relationship gets going.

She’s leaving with it in her purse.

I asked them to put it in my purse afterward because if it’s a cop, they committed the crime. If we were to do something and I got paid before, I could get in trouble technically.

They would have to participate.

It’s not that I’ve ever been worried, but that’s my precaution.

You are willing to risk not getting paid in order to not get caught.

You have them put it in your purse rather than hand it to you. Tell me why.

One of the first guys I met did that, and I was like, “I like that.” If a guy tries to hand me money, I say, “Put it in my bag.” Usually, it’s an envelope or something. It’s not straight cash.

That’s old school. It’s fascinating. I’m surprised to hear that cash is involved. I thought it would be Cash App, Venmo, buying gifts off of someone’s Amazon Wish List, or taking someone shopping. Let’s talk a little bit about the nature of the exchange.

When I first started, I was scared the government was going to catch me where they’d be like, “Where’s she getting all this money?” I was scared, but then my friends were like, “You’re not making that much to where someone will look into your bank account.” I had gotten cash sometimes. The guy who lives in Singapore does Zelle payments, but he gets nervous about that. He pays me in cash when he’s here for two months.

The Singaporean government has its business in everybody’s business.

I don’t know why that would bother them. What does it matter? He can give up to $10,000 of gifts a year.

Maybe he doesn’t want the paper trail.

My friend who has a sugar daddy was like, “Always get bank transfer, because you can always say it’s a gift and it’s on the guy to file that.” It’s not my problem that someone sent me money. It’s their problem.

I can understand that, but there are also these other exchanges that exist. It sounds like they’re not the case for you, but this Amazon Wish List thing was a revelation to me that people create a wish list. I don’t know how much of it feels less like a payment or less like that sex work slide of the continuum and more like the courtship side of the thing where you suddenly get some packages in the mail of nice things that you were hoping to get.

That seems more for like a virtual relationship to me. I follow a girl on Tik Tok. She has an Amazon Wish List and guys send her stuff. They also send her lingerie to take pictures in. She just gets paid on Venmo. She’s not meeting anyone. They’re just sending her stuff like that, and her wish list is linked on her profile, but I’ve never done that.

The last thing is there’s this pay-to-play mode and this more lifestyle or girlfriend mode. How does this stuff play out, and most importantly, how does this stuff get negotiated? I assume it gets negotiated at that meal. Is it awkward? Tell me everything.

It should be up to the sugar daddy. A part of it to me is if you are a sugar daddy, you need to be an alpha or a dominant guy, and it’s your job to get this conversation out of the way.

For our bonus material, as a teaser, if you want to sign up for the community, it’s PeterMcGraw.org/Solo. I’ll tell you my story, and that’s exactly what happened. He brought it up. That seemed bold to me, but evidently, it’s best practice.

I hate asking. I don’t want to ask for money. I want you to want to give me money. Does that make sense?

Yeah. I can see that.

I always try to talk to guys, like, “What are you looking for?” very explicitly. I’m like, “What would an arrangement look like with you?”

Is this after the appetizers have arrived?

No. This is before we meet because I don’t want to meet someone who’s looking for a one-night thing. There are a lot of people who are doing pay-per-meet, and I’m not interested in that.

Do you want an ongoing relationship?

Yeah.

Billy understands the concept of customer lifetime value that I teach my MBA students. You don’t need that Master’s degree. Do you check it out in advance if they want ongoing arrangements?

Yes. That’s the difference.

Let’s say he says yes, so you choose a place that’s not the Spaghetti Factory. The person looks like they’re not appalling. You’re essentially making small talk and waiting for him to at some point say, “You seem pretty great.”

That’s what it is like. I went on a date and we went out for tacos. We talked for a little bit first, and he’s like, “Do you have an allowance in mind?” I was like, “That’s normally up for the daddies to decide.” He’s like, “I don’t think it is,” and I was like, “It is.”

You’re like, “Make me an offer.”

What happened?

He was like, “How does $2,000 a month sound for four meetups a month, and one would be overnight, but the other ones would be during the day?” I was like, “That sounds good.”

What went on?

He texted me. He said he got a new house. He’s like, “I don’t have a Mercedes and my house isn’t the best house in the world, but I do have extra income to spend on this. I wouldn’t get to date someone as pretty and as young as you if I wasn’t paying for this.”

We forgot about this in the other list. Why do people do it? Some of it is they get someone out of their league.

If you were going on a normal date with someone and you were deciding, “Do I want to date this person again?” I’m guessing that sometimes it would be a hard no, and with this lubricant, it would be yes.

I only will do it if they’re attractive.

They have to be above some bar.

I’m not going to do it with anyone.

It sounds like this guy likes you.

I hope so. I don’t know. He was a little concerned. He was like, “You don’t seem very outdoorsy,” and I’m like, “I’m not.” He’s like, “I don’t know what we would do together besides go out to eat.” I’m like, “I went on a comedy date once, and that was probably the first date I’ve ever done that wasn’t just dinner.”

You’re like, “I’m happy doing dinner.”

He was like, “I would want to go hiking.” I was like, “In the snow when it’s cold? I’ll try it as long as it’s not hard.”

This didn’t sound exactly ideal then.

I don’t think Colorado is my ideal. I got to be flexible here.

Billy has said that the LA scene would be much better for her. I could see that in terms of cultural experiences. Are we missing anything else about how it gets started and who are the people? It also sounds like there’s a little bit of a negotiation that happens in terms of the amounts and the number of days. It seems like this overnight thing is a thing, whether it’s wanted or not wanted. Is there anything else that is the basics of it? We’re about to pivot for our last bit here about are there any other best practices. I’m going to basically say, imagine I have an audience who wants to be a daddy, a mommy, or a baby, what are their best practices? Is there anything else that comes to mind before we pivot into that?

No.

Here’s one more thing before we go to best practices. You’ve been doing this for a couple of years. What have you learned about yourself through this process?

It’s mostly that I’m a lot more confident than I think I am because I meet people and they’re like, “You’re really confident,” and I’m like, “I don’t feel like I am at all,” but I also realize I’m a lot more mature than I think I am. I’ve been on dates with older guys with a friend. I’ll bring my friend or I’ll be accompanying them and I can’t believe how they’re acting in front of an older guy. I’m a good actor in a way. I’m not pretending to be anyone. I just don’t act like a silly 25-year-old if that makes sense. The biggest thing I learned about myself is not everyone can be a sugar baby, and I have the skills that it takes to do it, so that’s cool.

Also, at your age, being able to define what you want clearly and stick with that, that’s huge. There are a lot of people who have a hard time defining what they want, verbalizing it, or asking for it.

I have a saying to ask for what you want. This is a type of relationship where people actually ask for what they want, which a lot of people are afraid to ask for what they want because they’re afraid they’re going to get a no or that someone’s going to judge them negatively.

In this situation, there’s a line of guys waiting to meet you if someone doesn’t want to do what you want or if it’s not a match.

This is going to be a longer line if you’ve lived in LA.

I know. I got to get there.

Have them fly you there. Can you be on there and say, “I live in Denver. Are you going to fly me there?”

Yeah. You can do that. There’s a guy who wants to fly me to Vegas.

The problem is you’ve never met him before.

We FaceTimed, but it scares me because you’re staying at a hotel with them.

I understand.

I do have another rule, and it’s I don’t have sex on the first date, but it’s hard to like, “What’s the first date if you’re meeting someone for the weekend?”

He can afford for you to have your own hotel room.

That’s true, but even though they can afford it, they still don’t want to do that.

You get wealthy by not wasting your money.

A lot of people are rich, but they’re still cheap.

That’s fair. My only opinion in these things is if you have a good gut, trust your gut. If you have a bad gut, do the opposite of what your gut says. That’s my typical advice for people.

I had to do that. I was supposed to go to Vegas with a guy. We had our first date on Saturday night and we were going to leave Sunday morning. I told him after he bought the tickets, “I can’t go with you.”

What was it about him that made you not do it?

He didn’t want to do an allowance ever, and he was so full of himself. His job was a professional sport bettor. He was like, “I’m going to get a Tesla when the Super Bowl is over,” and I was like, “That’s not the kind of wealth I’m interested in.”

That’s someone who doesn’t have money now but thinks he’s going to have money. That sounds like a degenerate gambler.

I was like, “Don’t get on that website if you’re not giving out an allowance.” I told him afterward, “I’m sorry to do this to you,” but we did agree that we were just meeting and would see how it goes.

He’s going to Vegas anyway because he’s going to go gamble.

He was pretty mad.

Let’s close with some best practices. Imagine that you have a friend who’s interested in being a daddy, mommy, or a baby. What have we not covered from creating a good profile to safety? Is there anything that you would advise? If you had a friend who was like, “I want to get into this,” and you’re like, “Okay. This is what you need to know,” what would that be?

The first thing I always say is you have to have sex with them. There’s no getting out of that, because there are so many girls online who are like, “My sugar daddy sends me $5,000 a month and I don’t even show him naked photos of myself.” I’d be like, “You do and you’re lying. You’re spreading misinformation.” Girls will get on that site thinking, “I can talk to these lonely old men and they’re going to send me tons of money.”

My understanding is if you don’t want to have sex, you should do OnlyFans.

Many girls think that it’ll be easy to get guys to send them money. That’s how I always like to start it off. I’m like, “You’re going to have to have sex with an old man. If you can’t do that, don’t sign up.”

Thanks for cutting to the chase with the exclusive advice.

Do you have an age limit?

My thing is if they’re hot, they’re hot.

That’s fair.

The oldest guy I’ve been with was 58. Another thing I tell my friends if they want to do it, is you have to be a little bit more mature and direct. There are not those games that people my age are playing. It’s super common for my friends or people my age to be like, “I’m going to post a hot photo on Snapchat or Instagram purposefully for a guy.”

Like a thirst trap?

Yeah, but sometimes they’ll do it on a private story that only that person could see, but that person doesn’t know they’re the only person seeing it. There are not these mind games that come with it, so a lot of my friends get confused. They’re like, “It’s not working,” and I’m like, “Yeah, because they’re 40 and they’re working.” They’re like, “He hasn’t texted me back in two hours,” and I’d be like, “He has a real job.”

My Instagram game is terrible.

There are not these mind games that you’ll be playing with them, because I think most older guys figure that out quickly and they’re not interested. You have to like them. That’s the main thing. They can tell if you don’t like them at all because maybe you don’t like them sometimes.

You’re going to want to have to play. What advice would you give a mommy or daddy?

You have to be generous.

Don’t be cheap.

The biggest thing is it doesn’t matter if you see them or not but they get the allowance because I think it becomes a fine line of prostitution when it’s just when you see them and you’re doing a pay-per-meet thing. Even though you went to dinner or you ordered a take out, you’re essentially only paying them when you have sex with them. Being a good, true sugar daddy or mommy is more about the experiences and the lifestyle. It’s not just about giving someone money and having sex.

It’s more of a relationship.

It definitely can turn into a serious relationship, but it can stay casual too.

This is a good segue, Julie, because Carrie said to me, “Don’t date your clients.” She says if it’s an arrangement, keep it an arrangement. Don’t turn it into a boyfriend. This is her quote, which I really liked. She said, “You may end up broke and heartbroken,” but you disagree, so it’s possible that an arrangement may turn into more of a traditional relationship.

It’s possible. I want to get married to a rich person, so hopefully, one day.

You’re auditioning.

You should want to date them. If you’re doing it without wanting to date them, that doesn’t seem right. I don’t know. You should be interested in them.

This is a good insight. A lot of people from the outside see this more like sex work than dating, but the way you’re describing it is that it has elements of both to it where there is genuine affection, enjoyment, and I’m guessing laughs, fun, and connection. It would be ideal that you’re getting the best of both worlds. You’re getting both the convenience, the fantasy, and the money, as well as some companionship that’s built on some element of friendship.

The goal when it’s over is that you’re still friends. A lot of sugar daddies will be like, “I still talk to a lot of the girls I was with. They just moved somewhere else. Now that they’re done with school, they don’t need me.” That’s a good way to judge their character in a way.

I’m selling the shit out of this bonus material, but that also is an element of the story. Last call. Are they any other best practices? What about safety? You already said you don’t go to someone’s house without having met them before. Do you tell friends? I’ve heard stories of sugar babies in particular sharing stories, especially in communities like, “So-and-so, stay away from him,” but is there anything safety-wise that comes to mind besides meeting in public?

I always say meet in public and trust your gut. If you don’t think you should see them in private, maybe don’t. Obviously, use protection.

Thank you. That’s right. An extra payment does not mean that a condom is not going to get worn.

A lot of guys think that.

That the condom is negotiable if you get the price, right?

Yeah.

I’m glad you brought that up. That’s smart advice.

You could also get tested together.

That’s right. Julie, thank you so much for doing this.

This might be one of my favorite episodes so far.

It’s so fascinating. When I launched this show a few years ago, there was so much I didn’t know. I feel like in every episode, I learned something new. There were some more than others, but even researching this one was fascinating.

Billy, I really appreciate your honesty and sharing. It’s fascinating and there’s no judgment whatsoever. I can see how it makes sense for everyone. When he asked me to cohost with this one, I was like, “Sign me up.” I love it. It’s great. It’s serving people’s needs.

One of the things that I am a big proponent of is if you want to have a traditional long-term relationship, by all means, you should. If you want to go completely solo and be a loner and not date or have a relationship, go for it as you should. If you want to find a way to have a relationship that’s unconventional in some way, like it’s consensually non-monogamous, maybe you live apart, maybe it’s polyamorous, maybe it’s a sexual friendship or an arrangement, go for it. I’m a believer in doing no harm and having consent. As long as those things are in play, I think that adults should be adults.

I want to echo what Julie said. Billy, you’re an outstanding guest because of your authenticity and your patience with us in terms of asking these questions, but I also think that it’s useful to give people an alternative perspective because there might be people that go, “I might want to try that,” or there may be people who were really quite judgmental before they understood the nature of this. Thank you so much.

Thank you.

Cheers.

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About Julie Nirvelli

SOLO 103 | Seeking ArrangementsJulie Nirvelli is a frequent guest and co-host on Solo. She was born and raised in San Jose, CA and earned her college degree from Cal Poly, San Luis Obispo.

She has lived in Colorado for 17+ years. As a strong, independent and fun-loving person, Julie embraces the solo life. She is also a sponsor of the podcast, with her company Bachelor Girl productions, which offers you fun flirty t-shirts.

 

About Billy Anonymous

Billy is a pseudonym for our guest who is a sugar baby. She studied apparel merchandising at University. Billy loves fashion, travel pop culture, veganism, and weight lifting. Kim Kardashian is her hero.

 

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