By Jessica Chou
Refinery29 has interviewed plenty of sugar babies before — both male and female — but what is it like on the other financial end of this transaction? Here, we interview one 40-something sugar mama who uses Arrangement.com to find her sugar babies — all four of them.
Tell me about why you decided to try sugar dating?
“Honestly, a friend had recommended that I try something like this. I work in the legal profession and I’ve just been really busy pursuing my career, so it was hard to find time to date in the traditional ways. And, I was getting a little too old to be going on all these one-on-one dates all the time where it wasn’t going anywhere. I did want to find that intimacy physically but I didn’t want to be just trying in bars. I felt like I was closing the chapter on that part of my life. So I decided that it would be good to have these arrangements where I could have companionship and regular company. It was just an easier way to meet my lifestyle and what I needed right now.”
Can you tell me a little bit about your dating history?
“My dating life in my 20s was really boring. I had a long-term boyfriend for about 3 years and it was fun, but then I went to law school kind of late, and once I went into law school, I decided I wanted to pursue that. So I just started getting really busy, and that relationship fell apart. Our careers were just going in different directions.
“Since then, it’s just been hard to find someone consistent. I’d meet someone, and we’d start and stop for two months at a time, and it was just exhausting. You know, we would get into that honeymoon period, and then it would be like, Oh, I want to see you several nights a week. I just had other priorities, and it’s hard to foster real intimacy if you’re not putting the other person first, and to be honest I was putting my work first. I think once you get into your early 30s, a lot of men, whether or not they want to admit it, want to settle down and I just wasn’t fitting in the mould of what a typical 31 or 32-year-old woman wanted. So it just kept happening over and over again and I realised that it just wasn’t giving me what I needed and I wasn’t being fair to them.”
So now that you’ve moved up the corporate ladder, how much money are you making?
“Before bonuses, $300k to $350k (£225k to £260k), and with bonuses, that varies year to year but that could go up to $500,000 (£375,000).”
Did you find that your salary was becoming an issue when you were going through the traditional dating routes?
“I do think so. I don’t announce how much I make on dates, but it does come up in the clothes I wear and the accessories I own at a certain point. But men in my income bracket or above were looking for women with more traditional values who wanted to settle down so the guys who were available for me, sometimes they just weren’t mature enough to handle someone who was making as much money as me, or someone who was dominating her career. There were a lot of egos being wounded with the men who were left.”
Can you tell me about a specific example?
“I always try to pay for my own dinner on dates even before I got into sugar dating. It was just something I had grown up with paying for my own meals and drinks. I can’t think of any particular horror stories, but I remember evenings of me pulling out my black Amex and getting a reaction. Which is silly because you shouldn’t feel shy for having high limits on your credit card.”
So you started sugar dating because you were working 24/7, and didn’t really have time to be vetting people through traditional dating routes?
“I mean I didn’t really want it to be 24/7, but unfortunately that’s just the reality of the industry I’m in. And I signed up for it, so it’s ok. I also wasn’t interested in pursuing something more serious at 32 or 33.”
Then why even bother dating?
“I mean, I guess woman to woman, I have needs. [laughs]
“If I’m being truly honest, and maybe this is something my therapist would agree with, but I guess I wanted to have my cake and eat it too. I wanted to have someone who would be more than just a sexual partner, someone who would give me that companionship and conversation and be my date to events. The people I was meeting who were okay with it being really casual, it was too casual for what I wanted from a man. I want someone who when I’m free, we can hang out, we can be intimate, but we can also enjoy dinner together and have that relationship build in a way that’s more than friendly, but I don’t have to give you more of myself. I’m very career-oriented and ambitious, so I wanted someone who understood that there would always be that reservation on my side, but would also be more than someone who I met up with at 3 a.m. in the morning to have sex.”
The key phrase there being ‘When I’m free?’
“Exactly. It’s on my time, and that’s a little selfish, but I just want to be up front about that. I’m in a selfish frame of mind right now.”
Tell me about your arrangements. What was the first date you went on?
“Okay so I heard about it at the end of last year, about a couple different sites, and someone was like, you just set the expectations up front. There’s no weird negotiating awkwardness. I was like, Oh I’ll do this as a joke, but it’s been almost 10 months now.
I have about four sugar babies that are regular. I don’t think any of them are making more than $60,000 (£45,000). The oldest one is 36 but apart from him everyone is under 31. 26, 27, and 31. We’re all free to date other people, and I’m very upfront about what our relationship is, but right now I feel like we’re all on a similar page that I expect to have all four of them around for the holidays.”
Were you dating younger men before you started sugar dating?
“I’ve definitely dated younger men in the past because of where they are in life. They’re not looking to settle down, either. I was meeting people through traditional apps and through friends — like oh my friend has a young roommate you should meet, or hey we’re going to a concert tonight maybe you’ll meet someone at the bar, kind of those ways. But I think trying to do sugar dating on your own without a formal setup is awkward. You don’t want to offend anyone by proposing something, so I just wanted to avoid that mess. So Arrangement.com was my first time doing it officially.”
What was your first experience like?
“Honestly, it was a little alarming. Just how honest the platform wants you to be and how honest the people you meet on there are. But once you get over that culture shock, it’s really refreshing to cut through the bullshit. This is what I want, this is what I can give, and either you agree to these terms or you don’t. I think just laying it on the table like a contract is helpful. Especially if you’re dealing with something that’s not traditional. It avoids hurt feelings; it avoids misunderstandings.
My first arrangement date, I was looking for a date to my friend’s engagement party. It would’ve been fine for me to go on my own, but I just wanted to bring someone. So I met a guy on the site, he was like 29 or 28? He was a musician. He went with me to the event and afterwards we went out to a rooftop bar and went back to my place from there. It didn’t end up being an arrangement — I got a bit of cold feet, so it ended up being a one-night stand sort of situation.”
Can you tell whether or not someone will work for you based on the profile?
“Sometimes I can just eyeball a profile and go, well, he’s going to be needy. They get a little too romantic, or say things like, I love cougars, and sometimes it’s clear that it’s either a fetish or some sort of romantic vision they’re hoping to gain that I’m personally not prepared to give. So I usually screen out anyone who looks like they’re talking too much about candlelight and rose petals. I just don’t have time for that.
“Or, I can tell if he’s going to hit me up for money, without really trying to form a relationship or friendship in there. That’s sometimes harder to gauge, but it’s the profiles where they have a la carte menus. For x gift, for x amount of money, I will be willing to participate in certain activities. That sort of thing.”
Have you ever had an experience where you felt like someone was just using you for money?
“I’ve only ever had that happen once, where after a few encounters the guy started making specific requests for things. I’m pretty generous on my own, but he was making requests and it stopped feeling like we were building a friendship. I felt more like an ATM machine.”
Tell me about your primary sugar baby.
“He’s 27-years-old, and he was the first one that I was very frank about. I didn’t bring him to any events with my friends, which is I think what made my first sugar dating experience a little too close to home. We just went to dinner and met up and had a conversation. He’s fun, a little immature. I don’t think think outside of our arrangement he would be like my husband or anything. We had a good time, though, and we kept hanging out and there are parts of my personality that come alive with him.”
What do you mean?
“I think my work is very serious and I’m so busy all the time that it’s refreshing to be with someone who is young and lively. I think that spontaneity and the life without a plan is so different than the life I’m living, that sometimes it helps me loosen up a little bit. So that’s fun. I don’t think this is a forever thing, but the times that we’re together I enjoy, and I know he gets things out of it, too, the same way I do.”
So what are the terms of the arrangement?
“The terms of this arrangement are very loose. It’s like hey, I’m going to be free on Thursday around 10 or 11. Do you want to do something? I do pay for everything when we go on vacations, and his apartment lease ended at the end of June, so when he re-signed his lease I offered to take over paying the rent, but that was after a couple of months. The rent is $1800 a month.”
Tell me about the other three.
“The 26-year-old is also in grad school. He is young, he’s fun. The one who is 31, he works in medicine. I think he’s a resident or something so his hours are also really crazy, so I don’t see him as much. And then the 36-year-old works in business. I don’t know if maybe I’m not using the platform correctly, but I don’t have any strict terms. Everyone lives in New York, so it’s just if you text and I’m not available, I’m not available. And if I text and you’re not available, that’s how it is. I’m sure other people have more strict every Tuesdays, or once a month dates, but mine are pretty casual. It’s just easier for me to keep a group of a couple of people because my schedule can be so unpredictable.
“So the one whose rent I pay, I see him probably once a week. And the other ones, I’d say probably maybe once a month? If six weeks pass and I don’t see one of them, I might give them a ring. Also sometimes I just want time for myself. Sometimes I don’t want to call one of the four guys I can call. I just want to stay home and do what I need to do. But I am pretty busy so they all know I can be challenging to get a hold of.”
How much would you say you’re spending on dating a month?
“For the 27-year-old, the one I’ve known the longest, for him I probably spend, maybe $6,000, or $7,000 (£5,250). We’ll go to events or nice dinners and I’ll shell out for us to do grand things. Listen, I’m a foodie. I love to travel, so if there’s something happening, I want to do a cool VIP experience or something, he’s probably the first one I’ll call because he’s fun and he’s a little more available. The other ones, it’s more like a couple thousand a month.”
So you’re primarily spending on the experiences? Do you give them any allowances or money for other things?
“One of my girlfriends was saying I should give him a gift allowance. So he can buy me things, but I haven’t initiated that yet. That’s an idea I’m toying with.”
How much would that gift allowance be?
“If I were to give them a gift fund, I’d maybe start at $10,000 to $15,000 (£7,500 to £11,250). And then we can go bigger from there, but I think that’s a nice start.”
What’s the most extravagant gift you’ve given a sugar baby?
Me and one of my sugar babies went to Switzerland last year. We flew first class, and while we were there, we took a helicopter up to see the town. We just shelled out. But I think now that I’m getting a little bit more comfortable with it, I want to start doing bigger things.”
What are you thinking?
“I like international trips, so I was thinking maybe Dubai. I’ve only been for work; I’d love to do that as a tourist. Someone was mentioning the Maldives so maybe in February. Bigger trips, bigger excursions, start checking things off my bucket list that I guess I was hanging onto and now that I have arrangements, I have people who can go to them with me.”
Are there any stereotypes about the sugar dating world you want to disprove?
“I think as a female sugar mama, and I hate that word, but I hate this idea that as an older woman who is accomplished and wants to pay for her arrangements, that that’s somehow deviant or abnormal. I think every relationship has a power dynamic, and my relationships are no different. We just spell it out on paper.”
Would you consider this sex work?
“I certainly don’t consider it sex work. Maybe my arrangements are unusual, but they all include some sort of conversation and other date-like aspects to it. It’s never, Just take $10,000 and let’s spend the weekend together with no talking, although that can be fun of course. But I don’t think it’s sex work. I think it’s just being upfront. I mean would you call a date with someone who buys you dinner, and then you go home with him, is that you being a sex worker? I don’t think so. We’re just more upfront about it. I actually think my relationships are more honest than a lot of the marriages and partnerships I see around me.”
What do you mean by that? That your relationships might be more honest?
“I just know some of my girlfriends, they’ll tell me things like, Oh my husband spent so much money on this thing and he didn’t consult me. I had to buy these things and had to get his approval first, or I went behind his back, I hope he doesn’t see the credit card bill. Just weird things about money that create these unnecessary secrets. But I’ve had a sugar baby say, Hey, I heard this cool thing is happening. Here are the tickets, we can take a helicopter, it’s going to cost a couple thousand dollars, and here’s where we can eat and here’s where we can stay, and we can just be upfront about it. Is that something you want to buy? There’s no hiding or manipulating or trying to convince someone. I just think with my girlfriends there’s this fear to talk about money, especially if they’re not the primary breadwinner in the relationship.”
Are you finding that your sugar babies will do more of the work of planning a date?
“I think so! I think maybe because I’ve always been upfront about the fact that my time is limited, so if I’m going to dedicate my time with you, you have to make it worthwhile. Also with the dynamic of me paying for it, for them planning is a way for them to contribute to the event.”
Do you think you might want something more serious in the long run?
“I wouldn’t say right now I want something more serious. Do I see myself having arrangements like these when I’m 60? Probably not. But for right now, it’s a lot of fun. But who knows? If all the people I’m with right now fall into more traditional relationships and our arrangements end, maybe I’ll be more inclined to do more traditional dating myself. I have nothing against traditional dating. I have had regular boyfriends in the past, but for now, it’s just a good time.”
Would you have ever considered doing the reverse? Being a sugar baby?
“I don’t think so. I have nothing against women who want to play that role, I just know myself. I’m so career driven and independent, I don’t think my pride would allow me to do it. I don’t know if I would allow myself to be on the other end of the arrangement. I respect women who do, I just don’t think it would work for me. Also, I think as a woman, especially in the time that we’re living in where women’s rights and feminism is so dominating the public conversation, for me it would be taking a personal step back. I would rather have a more traditional relationship if I were on the other end of the income spectrum.”
So now that you’re doing most of the paying, do you think there’s a stigma to a woman paying on dates?
“For me there’s no stigma. I feel a sense of pride of being a woman who can afford her own life. I own the condo I’m living in. I can afford to do the things that I want, so for me it’s a sense of empowerment that I can not only pay for myself — but help someone else who is not doing so well and could really just use a leg up. I actually get turned on from it, that I’m so in control.
When I was younger in my late teens and early 20s before I started really working, if someone said they were going to buy food then I would be like, okay well maybe I shouldn’t get a cocktail; if they’re going to pay for it, I can’t get something too expensive. So it’s nice now: I can get whatever I want, and I can tell other people, Hey get whatever you want. Get two drinks. Let’s get the whole bottle.”
Originally published at https://www.refinery29.com.