How to Find Your Own Sugar Daddy (Like I Did)

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It all started two years ago when my bulldog, Hemingway, got sick. After the $500 I’d dropped at the vet, I couldn’t even afford a cab home. And all the freelance work I could find wouldn’t come close to footing the impending bills. Huddled at the bus stop, Hemingway drooling on my knee, I Googled: “How to find a sugar daddy.”

But I’d always been curious. I imagined my life with a sugar daddy to look like a mash-up between an old black-and-white movie and a rap video — with ample time left over to write the Next Great American Something. There would be shopping in Milan, swimming in the Maldives, and gambling in Monaco. In other words, a fantasy complete with five-star pet care.

I created accounts on several websites. Every week or two, I would meet another potential sugar daddy. Six months and as many unpaid vet bills later, I found a nerdy-cute i-banker in his late thirties; Eli immediately took care of my debt and transferred Hemingway to the city’s best vet. Still, I took it slow. On our fifth date, he offered me $2,500 a month so I could relax with my dog. That night, Eli got lucky, too.

Two months later, I had to put Hemingway down. In my depression, I buried myself in Eli’s bed, welcoming the high-thread-count comfort of his luxury loft. He soon convinced me to move in. This was how I inadvertently let him into the “boyfriend zone.” In turn, I got to shop more, join his fancy gym, and eat at fabulous restaurants nightly. Tropical vacations and designer lingerie are decadent, but the habitual treats — like organic groceries, a cleaning lady, and pedicures — are what had me hooked.

Eyebrows may raise, but I see no moral issue here. In fact, if there’s anything unbalanced about this equation, it’s in his favor. I give Eli what money is worthless without: friendship and fun. Plus great sex. That, by the way, is the easy part. It’s the emotional labor that’s challenging: I do all the grown-up relationship work, from planning our dates to downright mothering. If I don’t properly tend his every need, a tantrum erupts: “You ate all the Häagen-Dazs? You’re just using me! It’s over!” Ultimately, being paid to put up with these pathological antics is toxic.

I know I have to quit — but I dread the thought of reverting back to a bodega-based diet or, God forbid, drugstore makeup. Despite these fallbacks, many of my girlfriends — from the bossy professional to those of DIY anarchist persuasion — still ask for pointers on acquiring their own sugar daddy. Here’s what I tell them.

1. Be Persistent on the Hunt.
You’ll have to sweet talk an army of frogs before you meet one you could imagine having sex with. I met Eli on SeekingArrangement.com, the most popular and direct sugar-dating service. With WhatsYourPrice.com, guys bid for first dates; pocketing a couple Franklins for showing up never sucks. For a less seedy option, try searching OKCupid by salary. Determine your boundaries (I wasn’t comfortable meeting men that were married or over 50, for example), then snap a few suggestive selfies. If your photos are too trashy, you’ll be treated like a prostitute.

When you find a potential match, pick a swank restaurant so you know he really has money. Your worst-case scenario now includes an epic meal. Ask lots of questions. Some guys expect further ego stroking, but I played the smart-but-free-spirited angle instead: more Holly Golightly than Holly Madison. “I just want to see the world and tell meaningful stories,” I’d say wistfully. “Where do you want to travel first?” they’d respond on cue. Know your approach and stay consistent.

2. Know Your Roles … and Play With Others on the Side.
These guys are good at making money, not having a girlfriend. So take advantage of that and just enjoy the exciting experiences (he’s paying for) together — be it on Broadway or in Bali. Unlike I did, avoid domesticity and limit dates to two or three nights a week. Not only is this more manageable, but your unavailability keeps him interested.

The job description of a sugar baby, as we’re called, is to be fun, happy, busy, sexy, and mysterious. Other feelings freak sugar daddies out — so if you aren’t happy or busy enough, embellish! Text him photos of stylish parties stolen from Instagram while you watch Girls and eat rice pudding alone, on your period. Keep your emotional needs in check via friends and lovers (but don’t mention these “support networks” to your sugar daddy, especially when monogamy is assumed).

3. Get the Bang for Your Buck (He Is).
Ask him to spring for a personal trainer and regular spa days so you can look your best for him. Wait until he’s in a good mood to shoot him a sext with a link to those Jimmy Choos (“ … and I’d wear only these”). Before any trip or party, explain that you don’t own a stitch of appropriate clothing (“but this is a Michelin-starred tapas restaurant!”). Shopping may not be your sugar daddy’s idea of a romantic date, so aim to engrave his plastic with your name.

The appeal of a sugar daddy is obvious: fantastic meals, exotic vacations, a fierce wardrobe, and even rent money. But being a sugar baby isn’t a sustainable lifestyle. It’s an adventure. And as Hemingway — the novelist — once said, “it is the journey that matters, in the end.”

Ariel Black is a pseudonym for a writer who lives in New York.