To overcome my reservations about walking the line between dating and prostitution, I told myself that any such concerns were the result of societal conditioning. The idea that mixing money and mating is inherently bad, I reasoned, was a fallacy based on our collective obsession with moralizing sex. Mating rituals involving the exchange of gifts—be they hunks of meat, small fishes, or diamond rings—are ingrained in many species, from apes to seabirds, to humans. It is only natural for males to target cues to fertility such as youth and beauty, and for females to be drawn to displays of resources. Why sneer at suspected gold diggers like Heather Mills or the late Anna Nicole Smith if they were merely following their evolutionary instincts?
With all of this in mind, I created my Seeking Arrangement profile. Since I was still a bit hesitant about how far I’d be willing to take my experiment, I signed up using the pseudonym Annabelle Walker. The site, which launched in 2006, has about 420,000 members, of which roughly one-third are sugar daddies and two-thirds are sugar babies (sugar mommies account for less than one percent). While sugar daddies pay $49.95 per month for a premium membership (or $1,200 a month for Diamond Club certification, which requires verification of one’s net worth through tax-return data), as a sugar baby I was able to join for free. I uploaded two photos and listed some general information about myself, and I stated “open, amount negotiable” in the space that asks what you’re looking for. (Seeking Arrangement skirts the issue of prostitution by promoting the exchange of “intimacy and companionship” for “gifts.”) I took a deep breath and posted my profile, determined to focus on New York–based single men claiming to be worth at least $10 million.