I Heart a Sugar Daddy

Confessions of an unabashed gold digger
“Can we line up and slap you?” That was the reaction I got from my closest friends when I told them about my new adventure in online dating. They were appalled.
Now, at first glance my profile reveals nothing slap-worthy: “I’m considerate and sweet yet independent and am looking for the same. I’m open-minded . . . I take good care of myself mentally and physically and try to focus on the good in life.”
It’s the site itself, and what it stands for, that has inspired such disgust from my friends and led me to keep all this a secret from my family, and to stay anonymous here. The dating site is called sugardaddyforme.com, and it connects wealthy men with women who want to be financially cared for. I know what it sounds like, and why my friends were so grossed out: It seems seedy, like prostitution.
On some level I agree with the doubters, because I’ve always thought it was shallow to want someone with money. If you’d told me five years ago I’d be doing this, I would have laughed in your face. I would’ve imagined nothing but gender role stereotypes and gross expectations on both sides. I’m the kind of person who has always been fiercely independent and paid her own way.
But I’m also the kind of person who is broke, and tired of it. I grew up with no money, the daughter of a fire-and-brimstone Pentecostal preacher who put my needs second to those of his flock. We were a family of five who got by on $20,000 a year, eating government cheese. I went to college on a grant and eventually cofounded a fairly successful business in Atlanta. Despite that success, my financial situation has never improved much. I still can’t really afford to go to the doctor or the dentist, and when I’m thirsty at the gas station, I do some silent accounting to decide whether I should buy a fountain soda. Unfortunately, the men I’ve dated over the years have been just as strapped as me. One guy had legal issues, and we’d fight all the time about them. I’d want to talk about it, and he’d run out. It drove me up the wall and made me insecure, but I kept trying. Another lied to me, mostly about whether he was spending time with an ex-girlfriend. I’d give him the benefit of a doubt, even going to therapy with him so we could work out those differences. But he kept lying about who he was, and eventually I just had to walk away.
So I found myself, at thirty-five, single and exhausted and yearning for something casual and simple and comfortable. That’s when I heard about sugardaddyforme.com and signed up on a lark. The offers came fast. One guy invited me for a weekend away in Chicago. Another, a fifty-something retiree, said he wanted to go on a date but never followed up. Eventually I connected with a guy I’ll call Kevin. In the photos on his profile he was hot: a young-looking forty-something with bulging biceps visible through the sleeves of his button-down shirt. He was a rich executive in Atlanta, and we started by e-mailing and then talking on the phone. We both wanted something casual but very honest, and he said he wanted to pamper me.
We planned to meet for our first date at my house, but he changed his mind and asked me to meet at the Best Buy parking lot on Moreland Avenue. Sitting in my beat-up car, waiting for him to pull into the lot, I didn’t feel scared. I was excited to be trying on a new persona and dipping a toe into a mysterious dating practice far outside my comfort zone of hipster bars, galleries, and setups by friends.
When he pulled up I realized why he wanted to meet here instead of on my narrow street: He was driving a gigantic blue Hummer. He threw open the door. The stereo was blaring Lil Wayne, and as soon as I hopped in he handed me a blunt. “Let’s skip all the awkward small talk,” he said, flashing a great smile. “Let’s pretend like we’ve known each other forever. So how was your day?”
I was at ease immediately. We talked about our professional roles, his at a big-name corporation and mine at my small business. I was attracted to him, and appreciated that he understood what I wanted: fun and financial support. No apologies.
Then the bubble burst: He told me he was married with kids. He explained that he and his wife had an “arrangement”: She knew he was unhappy, and she stuck around for the financial stability; divorce was unnecessary. I felt really uneasy about this at first—it clashed with my formerly staunch sisters-watch-out-for-each-other stance—but I admired that they were being real with each other and not faking it like a lot of married people do. A lot of the so-called rules for happiness don’t work out in the real world. I could relate to a woman who wanted the security of the marriage but liked an open arrangement. So I moved past it.
We spent most of the night at a club in Midtown where he was a VIP, and he held my hand and it felt good to be his arm candy. Maybe I was role-playing, and maybe it was cheesy when he called me “baby” and “honey” and fed me Patrón shots, but I liked it. When he dropped me off at my car at the end of the night, he insisted that I call and check in on my way home. He wanted to make sure I was safe. I liked this. So many of my boyfriends had never really seemed to care that much. It was nice to be coddled and protected.
It was after this first date that I decided to tell my closest friends during a dinner party. And really, I understood their misgivings. It makes sense that you might assume that with this kind of dating, the “sugar baby” should expect to offer sex. That it’s a transaction, and that sex is the return on the sugar daddy’s investment. I don’t view it that way. I don’t know if I’d have a different take if, say, my date had given me a diamond necklace or a wad of cash. But let’s be real here: All dating is transactional. Maybe the guy expects just closeness or gratitude, but maybe he expects sex. The transaction just isn’t discussed explicitly, because that’s not romantic. But with sugar daddy dating, there’s no coy behavior or uncertain terms. Everything is out on the table.
This explanation doesn’t placate some of my friends. None would admit during the dinner that they, too, fantasize about being taken care of and being involved in something simple and straightforward. Though later, one-on-one, a few told me that they do—they were just too ashamed to admit it to the group.
But not long after telling them I was happy as a sugar baby, I met someone outside the site, in the normal world. And wouldn’t you know it, he’s the best guy I’ve ever gone out with. He’s hot, a manly man who works with his hands. He’s also artistic, and we have an amazing intellectual and spiritual connection. He’s caring and considerate, and every time we get together he brings me a thoughtful gift, usually something he’s made.
But I’m not ready for this kind of connection. And I’ve realized that even though he’s the best guy I’ve met so far, I have higher standards. I can and should shoot for the moon. Every small detail about a guy matters now, and I can’t excuse things that don’t measure up to my expectations.
In this case, the greatest guy in the world is broke. So I cut it off, telling him I wasn’t ready for a relationship, not telling him why he wasn’t right and who else I’ve been seeing, and how I meet them. He said he’d wait, but I have to move on. —Anonymous, as told to Christine Van Dusen