Forget Love

Sugar Daddy Dating Sites: Helen Croydon on Her Guilty Fantasy

Tired of guys her own age, Helen Croydon joined a site ‘where the classy, attractive and affluent meet.’


I’d always had a penchant for older men. When I was 18, my first boyfriend was 32. My early crushes were always for suited-and-booted executive-looking types. Physically I find a face with experience attractive. Emotionally I’m drawn to their expressiveness.

I always felt embarrassed about it, though. My friends all seemed to drool over churlish boy-band types. It wasn’t until 2007, when at 29 I broke up with my boyfriend of three years, that I decided to explore my guilty fantasy of dating an older, wiser, more worldly type. My ex was suffocating. He wanted to do everything together, and I’ve always loved time alone. He didn’t have a regular job and paid rent only when he could afford it.

After our split I felt an overwhelming sense of freedom. I didn’t want another serious relationship, but I didn’t want one night stands—yuck. I wanted what I call a “low-maintenance relationship” with someone emotionally intelligent and mature.

So one evening, home alone with a glass of cheap white, I googled “older men, younger women, dating.” I ended up joining, a dating website that describes itself as a place “where the classy, attractive and affluent meet.” I never intended it to be anything more than a few glamorous dates, but it soon became an addiction.

My first date was a 45-year-old property lawyer. We met at a decadent Champagne bar on the 42nd floor in London’s financial district. He was handsome, intelligent, and interesting. But he waited until the date to tell me he was married. Although I wasn’t looking for a committed relationship, I definitely didn’t want to be a home wrecker, so the evening went no further than dinner.

I made sure my other dates were single. The next was an insurance firm CEO, off work while he was investigated for fraud. He took me for a Champagne breakfast as a first date because we couldn’t find an evening where we were both free. We drank Bollinger from 8 a.m. until noon in one of London’s finest hotels and then spent the afternoon in his junior suite.

There was a constant stream of interesting, often high-profile men on the website, and I thrived on the excitement of fresh encounters. Casual sex had never interested me before; I had always been a bit of a prude. But somehow no-strings sex in decadent surroundings was thrilling. I suppose I was turned on by meeting men in a higher social league than my beer-swilling peer group.

After a couple of months, however, I became aware of a subculture to the site where men offer gifts or financial support in return for a girl’s regular company. My dates told me that around half the women on the site make references to “monthly allowances” or “rent” in their opening messages. Several times I was propositioned. A typical message would read: “Like your profile. Am looking to meet 6-8 times/month. Can help with tuition fees/rent etc.”

I was naively shocked at first and deleted any such message. But slowly I grew more curious. One day an American banker invited me to accompany him on a business trip to New York. After several Skype chats I agreed. He flew me first class. I remember putting the seat back, sipping Champagne, and glowing at my good fortune. He took me shopping, insisting we go into designer shops. I felt awkward and it felt grabby to accept anything, so eventually he took the lead and told a Prada shop assistant to “look after me.” He bought nearly everything I tried on. I fancied him and we clicked, but neither of us made great efforts to see each other again. It was never about lasting relationships.

My moral boundaries relaxed after that. Then one day a close friend came to me in tears. It was a familiar story. She really liked a guy. He led her to believe he was serious but went cold once he’d got her into bed. It dawned on me that so-called sugar daddies are more honest. They use these websites because they want genuine companionship, but they’re too busy or travel too much to pursue a full-time relationship. A cash allowance is merely a replacement for what they can’t afford to invest emotionally. Given that I didn’t want a committed relationship and that I was genuinely attracted to these men, what was the harm in accepting payment for what I was already doing for free?

Put like that, when my next date, an attractive advertising exec from Chicago, made an indecent proposal, it didn’t seem so indecent. We drank dirty martinis in his fancy hotel piano bar, chatting about the forthcoming U.S. elections and the economy, and laughing about American-English anomalies. Suddenly he asked what it would take “to carry the night on,” and before I knew it I had accepted money to spend the night with someone. We didn’t even have sex, though. He held back because he said he “wanted to see me again.”

He became my first sugar daddy. He visited London about four times a year, and each time I would spend at least one night with him, always in a fabulous hotel and always preceded by a dinner full of laughter and stimulating conversation.

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After that it was easy to entertain other offers that once I would have sent straight to my delete bin. I formed two more “compensated relationships,” one with a London-based lawyer who suggested a generous pre-paid monthly store card at the upmarket Selfridges. We met once or twice a week and had occasional trips away, including a ski holiday to Colorado. Then there was my Malaysian sugar daddy, a philosophical man I came close to falling in love with. He was divorced and like me valued a close bond but didn’t want anything permanent. We saw each other every three or four months, and occasionally he would leave an envelope bursting with euro notes signed with the words “With Love.”

But the more I received, the more detached from the idea of a genuine relationship I became. I dismissed any man outside the website who expressed genuine romantic interest in me. What was the point? Love looked like a time-consuming inconvenience.

I attempted a couple of conventional dates with men my age, but they bored me and I was irritated to have wasted an evening. I was horrified at my reaction. When did I become arrogant enough to think that I should always be compensated for my time?

After a couple of years the thrill of a date with an older, wiser, higher-flying executive had faded, yet I was still chasing dates. I realized that my motivation had shifted to monetary gain. The allowances and gifts, which were once a happy bonus of my adventures, were now what was keeping me there. I knew I had to stop before I became even more hooked.

I stopped visiting such sites more than three years ago. Although I have no regrets, I would be lying if I said it didn’t affect my approach to relationships. My sugar daddies were chivalrous and respectful, but when someone is compensating you for your time, a power dynamic emerges. I always had to be on form, never my true self. Relationships seemed like a chore, and it was easier to stay free and single.

It was only a year ago that I allowed myself to fall in love properly. I’m very glad that my relationship now is based on parity and my rewards are genuine love and affection, instead of brown envelopes and Prada shopping trips. But I still believe sugar daddy dating sites serve a purpose. They offer a model of a relationship where two adults can have an honest, respectful, enjoyable but noncommittal relationship. Commitment and longevity are wonderful, but not every relationship has to be based on that all the time.

'Sugar Daddy Diaries: When a Fantasy Became an Obession' by Helen Croyden was published by Mainstream Publishing on May 1; $14.95.