Seeking Arrangement, a website that connects potential "sugar babies" with sugar daddies and mamas, has been around since 2006, but about once a year some enterprising reporter seems to discover it anew, thus provoking another round of incredulous blog posts and Tweets.
I signed up with Seeking Arrangement in 2010, when I was living in Brooklyn, NY and—due to rent, road trips and too many visits from the weed delivery service—somewhat cash-strapped. But more than that, I was curious. Single for more-or-less the first time since age 17, this was the same time period when I first began blushingly perusing the Craigslist casual encounters ads. I wanted adventure. I wanted money. This seemed like a good way to satisfy both needs.
So I created a seekingarrangement.com profile, carefully crafting my image as a young writer eager to rely on the kindness of strangers. And, soon enough, the messages began pouring in. What I hadn't accounted for was all the online communication necessary to weed the weirdos from anyone with potential—I can barely manage to keep in contact with the people I love, let alone find time or motivation to talk to would-be sugar daddies. I had all but declared the experiment a wash until one night in July when my house threw an afternoon party.
The afternoon party is only relevant because it involved a lot of drinking, early in the day. It also involved a lot of being around my most-recent ex, whom I was still living in the same house with. At some point, the combination of the two propelled me away from the crowd, up to my bedroom and onto Seeking Arrangement. I can't remember exactly how it happened, but I ended up agreeing to meet up with a man we'll call Dave at a bar in the Lower East Side.
Now, normally, you couldn't drag me from Brooklyn to Manhattan on a weekend if you told me there was a free Malbec, macaron and kitten party. The fact that I felt willing to do so explicitly says I was in no condition to do so. Because I knew my friends would try to stop me, I told no one. I snuck out, took that L train under the East River and considered what I knew about Dave: He was around 40. He was blond and a little stocky, according to his profile pictures. He was married (but no children). And he held some sort of job in the music industry.
This last bit was what made me settle on Dave, I think; we had exchanged messages about Arcade Fire and LCD Soundsystem, and he seemed like someone that, under other circumstances, I still might hang around. Sure enough, Dave did turn out to be easy to talk to. Conversation flowed naturally and normally, and I remember enjoying myself as we drank wine and discussed bands, life in NYC and why he was looking for a mistress. After the first round of drinks, he pulled out a wad of cash and handed it to me.
"Let me give this to you now, for your coming out to meet me," he said. "So you know I'm not bullshitting you. There will be a lot more if, you know, we decide you want to see me again."
I took the money sheepishly, without so much as glancing at how much it was, and put it in my purse. After another round or two of drinks, the entire day of drinking had really caught up with me. "I'm starting to get dizzy," I told him as we stood outside the bar smoking cigarettes together. "Let me put you in a cab," he said. "Or if you need to lay down first, my office is right around the corner."
Dave wasn't a bad-looking guy—a little chubby for me, a little short, but not bad. He looked a lot like the writer Chuck Klosterman, black-rimmed glasses and all. I'd been enjoying hanging out with him, and wanted him to like me. Plus, laying down did sound nice. "Let's go to your office," I said.
That is pretty much all I remember. If you're thinking "Oh, no, she was drugged!"—nope. I mean, I'm 99.9% certain that's a nope. I was just really drunk, way too drunk to have even left my house, let alone go somewhere alone with a stranger. Luckily, Dave did not turn out to be a rapist or a serial killer or anything else nefarious. I woke up the next morning on a couch, fully-clothed, with a blanket draped over me and a massive headache.
The first few minutes of that morning were mind-boggling. I looked around at my surroundings: A very large loft space, with one entire wall of windows. A desk toward the back of the room, separated from the couch I was on by a pool table and a pinball machine. I checked by body: Clothes in-tact, no sign of forced entry. On the table there was a note: "Liz, you passed out and I had to get back to my wife. Take care--there's vitamin water in the fridge. Talk to you soon."
At that point, Vitamin Water sounded like manna from Heaven. I made my way to the fridge, which was entirely full of nothing but Vitamin Water and Red Bull (I took two of the former and one of the latter). Then I remembered the money Dave had given me at the bar. I checked my purse: $200.
It was only about 6 a.m. at this point, a beautiful July morning. I decided to walk home across the Williamsburg Bridge, and as I did—barefoot, carrying my painful shoes, downing the grape Vitamin Water, smoking a cigarette—I'd like to tell you I was thinking about how lucky I was that nothing bad had happened. But all I remember thinking about was that this had been a strange adventure and the sun coming up over the East River made the whole world seem beautiful and full of potential.
Back home, I messaged Dave apologetically, and a few hours later he messaged back proclaiming it NBD. He'd had fun hanging out and wanted to see me again if I was into it. But I was too embarrassed by the whole thing by this point—the drunkenness, the passing out, the very fact of meeting up with a sugar daddy. It seemed somehow, suddenly, sordid. I vowed not to see Dave or use the site again.
Conviction, however, has never been my strong point. A few weeks later, I accepted a request to meetup with a youngish lawyer who wanted to go to Roberta's, a wood-fired pizza joint near where I lived. I'd frequented Roberta's when it first opened, back when it was still BYOB; but now it attracted Manhattanites who would otherwise never set foot in Bushwick, and there was always at least an hour wait on weekend nights. I don't think there was anything particularly exciting about the profile or online conversation between me and the lawyer, but he was legitimately attractive—thin, Asian, shaggy-haired—and I really liked Roberta's, so I agreed.
It didn't start off on a good note. One of the first things he said to me was "I'm not really looking for a sugar baby; I just thought this seemed like a way to meet cute girls."
This annoyed me,of course, because I wasn't looking for a boyfriend. I felt tricked, which is never a good way to start things off, and dude also turned out to be that awesomely obnoxious combination of boring and cocky. It became clear within about 10 minutes that we had absolutely no conversational chemistry. Later that night, I left him dancing in a group on the Roberta's patio, insisting he should stay and have fun and I could find my own way home, thanks.
My third and final foray into becoming a sugar baby involved a man who called himself Ralph. After the first two attempts, I decided maybe I needed to go more against type. Ralph looked to be in his 50s and his profile pic was him standing next to Dick Cheney. Bingo. He asked me to meet him in Midtown for tea, because he didn't drink.
Over tea, he told me how he lived in Connecticut but worked in the city (I want to say he lived in Greenwich, but I think that's just mis-remembering out of stereotype). He kept an apartment here for when he worked late. He hinted at belonging to either The Carlyle Group or the family that owned The Carlyle hotel, I couldn't discern which. After barely a few minutes of conversation, he wanted to get down to business: "So what kind of financial support are you expecting?"
"Ummmm .... uh ... I don't know."
"What kind of arrangement are you seeking, then?"
I didn't have a good answer here either. I am the worst sugar baby ever, I thought, and went with the ol' 'What are youuuu looking for?"
What Ralph was looking for was someone to meet him at his Midtown apartment, once or twice a week, for sex. Each time we met, he would give me $300, with bonuses for good behavior. Occasionally, he might want to go out to dinner or take me to a work event. His directness was admirable yet off-putting. Did I want to see the apartment when I finished my tea?
I agreed, though I was pretty certain this was not going to work out. Ralph looked like an older Baby Huey, and seemed to have a high-school nerd's chip on his shoulder. Back at his apartment--which was entirely empty, save for a few kitchen goods, some clothes in the closet and a mattress on the bedroom floor--Ralph cozied up and started kissing me. He smelled awful. "Tell me about what you were like in high school," he said.
"I ... went to Catholic high school for a bit, and then switched to public," I told him. "I got good grades. I ... was a cheerleader."
"Mmmm, my little cheerleader," Ralph said. "Did you wear a short, short skirt? Did you naughty things with the boys?"
Oh, gawd, it was too much. I can abide bad x-rated talk from someone sexy, but this just would not do. Unfortunately, Ralph was much less understanding than Dave. When I tried to politely excuse myself from the situation, I was met with more pawing and a side of guilt trip. I am probably going to regret admitting this, but I gave him head because it just seemed like the easiest and quickest way out of the situation. The whole time, he talked about my cheerleading uniform and Catholic school jumpers.
Afterwards, he gave me $300 and asked when he could see me again. I told him I would be out of town for the next two weeks (true) and would get in touch when I got back. I never did.
As I took the subway back to Brooklyn, I thought about all the different 'arrangements' I'd encountered people seeking. Anyone who looks at or uses the website can attest that the desires are diverse. There really are folks looking for totally non-sexual arrangements -- people to take to events, people to provide companionship, people to take shopping because they (the men) have shoe fetishes. There are sugar daddies looking for someone to fulfill all sorts of specific fetish requests, and those looking for an old-school style mistress arrangement (some complete with housing!). There are men who simply want a girlfriend that's hotter than they may get without a little financial incentive. There are those who really want genuine companionship, and see this as a short cut. There are those who want a girlfriend who won't make as many demands on them, whom they can essentially pay to not have hardcore needs and wants of her own.
And there are men, like Ralph, who mostly just want to pay women to meet them for sex. I guess in doing what I'd just done, I had just made myself a "whore." It didn't bother me too much, partly because I've turned down free drinks at bars from guys my whole life (part feminist principle, part misanthropy). I'd never expected or wanted dates to pay for me for anything. Meanwhile, I'd watched so many girlfriends over the years fool around with dudes they just weren't that into because they bought them jewelry, whiskey sours and concert tickets. 'Whoring' is just a matter of degrees, and I couldn't for the life of me believe this was qualitatively different than that. But really, most importantly, I just don't think having sex for money is necessarily anything to be ashamed about. I respect sex workers and I respect sugar babies. We've all got to eat, and some of us really don't like working in retail.
Nonetheless, I never met up with anyone from Seeking Arrangement again. Avoiding awkwardness is pretty much my MO in life; and my preferred method of dating is to have enough drunken conversations with someone that we start sleeping together and sleep with each another enough that we start considering ourselves a couple. Finding a sugar daddy seemed too much like traditional dating, and that was 100% what I did not want.
I feel like I should come up with some moral to this story, but there really is none. As far as takeaways: 1) I suck at being a sugar baby and 2) sugar daddies come in all stripes. Maybe this is my moral: That there is no one type of woman or man using this site, and its silly to make blanket conclusions about them. And maybe that you shouldn't get wasted before meeting a strange man for drinks? But, meh, I can't even say that with much conviction, because it worked out just fine for me. Maybe my moral is just that there doesn't need to be a serious moral served up with stories like this. Sometimes we randomly decide to meet strangers for strange sexual arrangements, and it's really just not that big of a deal.
Editor's Note: An earlier version of this piece appeared on lunalunamag.com, our old site, in 2013.