An NYC Sugar Baby’s Guide to Eating Out

The below was originally written as part of my “Sugar Babies” column for VICE:

Madeline is a 24-year-old artist living in New York. She’s been supplementing her income by dating men she meets on sugar daddy websites for over three years. I interviewed Madeline about her nightly exploits about a year ago, and we’ve since become close friends. She’s always making me jealous with all her stories about the fancy restaurants and bars she goes to on her sugar dates, and she knows more about fine dining menus and upscale hotels than anyone else I know, so I thought she’d be the perfect person to kick off Sugar Babies. Now we can all live vicariously through her stomach.

MUNCHIES: The general idea is that what separates a sugar baby from an escort is that sugar relationships are more like actual dating, whereas escorts just have sex for cash. Does that mean you always get fed before sex?
Madeline: Dates usually involve dinner, yeah. Or at least drinks. Most sugar daddies—or the good ones, anyway—understand that the sugar experience is supposed to be extravagant, kind of like a fantasy, so you get to go to some pretty nice restaurants. Over time, you start to learn that the restaurant a sugar daddy chooses for a first date is a good way to gauge his taste, and also how comfortable he is with spending money—it’s like a screening process. This one guy recently messaged me through a sugar daddy website asking if I wanted to meet him at a juice bar in the East Village… like, shoot me. The point is to take me somewhere I can’t go in my normal life, to impress me. I mean, if it’s not at least three dollar signs on Zagat, I’m not showing up.

What’s an example of a sugar daddy who went out of his way to impress you?
Well, I once had a client who was from a royal family in Saudi Arabia. He was married, so he flew me to meet him in Paris and put me in the Royal Monceau Hotel, which is so gorgeous. It was designed by Philippe Starck, who designs high-concept, luxurious hotels around the world—like he did the Delano in Miami, for example. The Royal Monceau feels a bit like the set of a David Lynch movie; there are these hallways with stripes running circularly around the walls, ceiling and carpet, with mirrors at either end. When I arrived to the room there was a bottle of Dom Perignon from my birth year (1989) on the bed. Apparently, 1989 is a really good year for wine, so that’s been “a thing” with some of my clients. When they find out my age they bring me ‘89 champagne.

Where did he take you to eat in Paris?
The first night, we went to a French restaurant called L’Ambroisie, in Place Vosges. Realistically, there are few non-French restaurants in Paris; the French aren’t big on variety. So L’Ambroisie has three Michelin stars and is really decadent and indulgent, but it’s kind of too much, actually—the total opposite of subtle. Like if you leaned forward in your chair to stand up, one of the staff would run over and move your chair for you. Every review I read of the place was like, “This is where people go to flash their cash—not because it’s the best food or the best experience, but because it’s the highest price tag in the city.”

So was the food bad?
I mean, you’d have one bite of something and be like, “that tasted nice,” but if you were to eat a full serving of any of it you’d feel sick because it’s so decadent. The Saudi guy was a very alpha-male type, so he ordered for me—he didn’t even look at me to see what I wanted. It was a twelve-course meal and everything had so much cream and caviar and gold flakes in it. I thought I was going to die.

Like literal flakes of gold?
I guess… like edible gold though, who fucking knows. I remember one course was foraged wild mushrooms that had been boiled in cream for five hours. It tasted like a weird, savory cappuccino. There were also soft-boiled eggs filled with caviar.

Ugggh, how do you have sex after that? I’d feel so fat and unsexy.
We had sex before we went to dinner. He was thinking ahead.

Phew. So what’s an example of a sugar date that felt extravagant, but in a more subtle way?
I like Jean-Georges in New York. It’s sophisticated and elegant, but the staff aren’t up your ass the entire time. The restaurant is on the ground floor of the Trump Tower. You know a sugar daddy is legit if he takes you to Jean-Georges and then tells you he lives upstairs.

Oh, I know Jean Georges because Samantha goes there on a date in Sex and the City. Who took you there?
He was an Indian lawyer. He was really young, actually, like 35. Most of my clients are in their 40s and 50s. It was his first time meeting someone from the sugar daddy site, so he was really giggly and nervous, and he kept talking about how India has a “super butter”—they boil butter and remove the extra liquid and just keep super fat; I think it’s called ghee or something. After dinner he gave me the really cliché sugar daddy line of “You have to come upstairs see the art in my apartment.” So I went up, and all the apartments at the Trump have crazy views of Central Park. He fucked me up against the window, obviously.

Hot. Do you remember the first time you were taken out for a really nice meal, when you felt like, “Wow, I never would have thought I would eat here”?
The first time I felt that was at Nobu, the Japanese restaurant in Tribeca. The sushi is amazing, but in hindsight it’s not even that crazy nice or unattainable. That was a few years ago, when I would have never spent $50 on a meal for myself. There was a point when my goal was never to spend more than $7 on food ever, like, ‘Why would I buy a glass of wine for $12 when I could buy a whole bottle of wine for $3 at Trader Joe’s?’ But now I’m an idiot with money, because it feels so disposable to me. When you’re handed $1k for one evening of easy work, you’re a lot more frivolous with your money than if you worked long and hard for it.

Who did you go to Nobu with?
Someone off Craigslist, actually. There was a time when I was going on a lot of dates with guys just for the dinners—so I wasn’t having sex with them—just because I wanted to try different restaurants. There are sometimes rich guys on Craigslist who post ads asking girls out for fancy dinners, because they’re lonely or have expense accounts or whatever. The first time I went to the Four Seasons was from a Craigslist ad actually. I remember cracking up in my head while sitting at the Four Seasons in my Louboutins eating oysters, sitting across from this tiny little bald man.

But isn’t that a major red flag? Like, “Hey I’m a hot blonde with a troll at one of the most expensive restaurants in the city.”
Yeah, but I can get off on that. I think it’s kind of hot that people know, or that they’re wondering what’s going on, or making assumptions. I don’t really care what a room of strangers thinks about me for an hour. I once winked at a guy and his wife who kept turning back to stare at me.

Lol. So what’s one of your favorite restaurants in New York?
I really love Milos, a Greek restaurant in Midtown. They have amazing fish—I always get market fish or some kind of raw fish. There’s some kind of baby octopus appetizer that’s incredible, too. My favorite thing about Milos is that when you ask about the wine, if you’re not savvy enough to know what every bottle is, if you describe what you want, they’ll bring you three different glasses and let you sample them so you end up getting something you really like. Also, Milos is really spacious with a lively atmosphere, and as an escort you learn that it’s best not to go to really mellow places where you’re shoulder-to-shoulder with other tables, because you inevitably end up having conversations that you don’t want other people to hear.

Do you sometimes negotiate the money over dinner?
Often, yeah—if it’s the first date. Actually, one of my dates at Milos was with an Academy Award-winning documentarian. It was a threesome thing, so I was there with one of my girlfriends who I escort with sometimes. So we told they guy that it’s going to be $1k each and he was like, “Well, I don’t know how much money I have on me.” It’s so annoying when guys are unprepared—like, how stupid are you that you didn’t remember to bring cash to meet your hooker? So my friend was like, “Well, I guess you’re going to have to go to the bathroom to count your money, aren’t you?” It was so funny. He shuffled off with his briefcase to count his cash in the bathroom stall.

One client actually paid me at the table. He told me it really turned him on to pass a girl a wad of cash under the table, and to know that it was making her panties wet. He’s a player who likes the idea of super slutty girls who would do anything for money. I don’t mind getting into that role play.

Where was that?
Well he told me that at Pravda, this subterranean Russian vodka bar in Nolita. He was really into martinis. And then the money was at Masa, which is this really amazing, insanely high priced Japanese restaurant in Columbus Circle. I like eating there because they have these cool Japanese toilettes with a bidet in them, which are really useful for cleaning your vag before sex, ha!

So do you always dress up?
I do. It plays into the fantasy experience I was talking about. For the first date I always try to wear something that shows cleavage and is fitted, but is still sophisticated and expensive looking. Around the third date you can tone it down a bit and wear something “cooler.” I’d never wear a mini skirt or anything really slutty because while I do like getting looks, I don’t want to get looks for being a cheap hooker. I want to get looks that say, “I could never afford her.”

Good tip! Have you ever been taken to eat somewhere really awful?
I once went to meet a client in Atlanta. He’s really sweet and has a lot of money, but he just has no taste for food or clothing, mainly because he just doesn’t care. So he told me we were going to Pappadeaux, and I’d never been to Atlanta so I didn’t know what anything was, and we show up and it’s this awful chain restaurant with a logo of a cartoon crustacean. It wasn’t as bad as Wendy’s, but it was the kind of place where there are stand-up menus with pictures of hurricane drinks. I obviously wouldn’t mind going there in my regular life, but I’d flown to Atlanta, and I was way overdressed in this Missoni dress and stilettos, and the guy next to us was literally wearing a bib for his oyster sauce [laughs]. And my date was just like, “Isn’t this great? So tasty!” He was so happy.