My Sugar Daddy Phase

Today I want to touch on a subject that I’d like to think I’ve officially put in my past. It’s one that’s earned me some criticism over the years, even from my closest friends. So let’s just get it over with and get it out in the open – and by “it” I mean my love of Sugar Daddies, and my Sugar Baby days.

I’ve dated a couple of quite older men, which may or may not come as a surprise to you. My senses of humor and perception have rather adult foundations and I’ve always been very mature for my age. So when I was 22, and picked up by a guy who was 36, even my mother wasn’t surprised, though she certainly wasn’t pleased.

The Surfer lived in Orange County (of course he did) and I met him on a layover at an airport bar (of course I did.) At the time, I was a senior in college and accustomed to boys that had to ask their parents for money so we could go on a date. But The Surfer was successful, at the top of his game and, as I have since realized, looking for a trophy wife. I wasn’t really sure what that entailed, but he certainly did have a nice house and I thought I looked good in his Ferrari. Plus, there was something to be said for having those new, deluxe experiences that were so unfamiliar to me. Drinking Dom Perignon on a carriage ride through downtown Chicago. Flying first class into LAX and sitting next to D-list celebrities. Of course, he was getting something in return, he had a cute 22-year-old to parade up and down Pacific Coast Highway. But he was good-looking, so it was a mutually beneficial relationship, with just a hint of financial power dynamics present.

Later on, when all was said and done between The Ex and me, I found myself back in the Sugar Baby game. Only this time, my motivations were far less pure and a lot more cynical, perhaps even predatory. The Ex, though not a bad person by any means, was very, very cheap. For instance, for the last nine months of our relationship he never once took me out to dinner because he “couldn’t afford it.” But that didn’t stop him from running up tabs at Elephant and Castle after work with his colleagues twice a week. So he was selectively frugal, and he selected me get screwed in that deal. Suddenly, the trophy wife thing started to look a whole lot more attractive. However the problem with that is the more an older man is willing to spoil you, the more likely it is he’s using his money to compensate for other things. And a lot of times, these deficiencies fall under an aesthetic, or even an anatomical, category. So then dating rich, older men started to make me feel a little bit like a courtesan. For those of you that aren’t up on your 16th-century terminology, I’ll save you the trouble of Googling that one: it means hooker. Moving on…

All of that changed that day I met the Renegade Millionaire. He was the oldest guy I’ve ever dated, at 23 years my senior when I was 26. But he was also one of the smartest, sexiest, funniest guys I’ve ever known. Our paths crossed under unusual circumstances in New York City last fall. Then he ended up flying back to Chicago with me to catch a Cubs’ Playoffs game. A few months later, we did Vegas, and we sure did do it in style; VIP all the way, from the high rollers tables to the strip clubs. I’ll never forget when he walked me into the Gucci store and let me pick out whichever handbag I wanted. But the difference between the Renegade Millionaire and the Sugar Daddy-types before him was that we had a genuine connection. I wasn’t just his arm candy and he wasn’t just my meal ticket. We had real conversations about life and love, art and music, politics and philosophy. If there wasn’t such an age difference (not to mention he lives in Seattle) I feel we could have even had a relationship. And to be honest, though I have no way of proving this, I think without his millions I still would have liked being with him.

But alas, I’ll never know that for sure. At least I hope not, as far as his security and happiness are concerned. What I do know is that I was, and always will be, grateful to have him in my life. Because the truth is, Sugar Daddies will come and go, depending on my age and their marital status. But a true friend and lover, millionaire or otherwise, even one that’s about to turn 50, will always have a place in my heart.

The bottom line, and what I’m trying to say is, after having what I’ve had with the Renegade Millionaire, I can no longer fuck older guys just for their money. Not in good faith, at least, and that seems like something I’m aspiring to have in the backdrop of my life these days. I can, however, continue to fuck older guys that have money (hey I’m not about to relegate myself to slumming it here) just as long as I find their personality far more attractive than I do their tax bracket. If you’re reading this, RM, and I know you are: thank you for teaching me that lesson….and for the purse.

xo