He lived in New York and I lived in Toronto, so our dynamic would be limited to the phone for the time being, though the possibility of in-person meetups was later floated, provided we hit it off via audio. (I don’t think this is something I’d still do now, BTW, unless the remuneration was significant, but back then I still had the time and energy for such things.) He was interested in setting up a phone chat to discuss “our relative perspectives on sexuality,” and also to do some phone sex-type stuff if I was up for that. The email was wordy and polite, explaining that he had heard my podcast and read my blog and followed my Twitter for quite some time, but had only just learned that I offered audio-chat sessions for a fee. I was at my optometrist’s office, of all places, sitting in the waiting room. I still vividly remember the moment I received an initial email from the man who would become my short-lived sugar daddy, because it soothed these insecurities like an ice pack held to a bruise. Hell, even now, at 31, I sometimes still narrow my eyes when someone cute expresses desire for me, like, How do I know you’re not lying, though? So it still surprised me, well into my twenties, when someone I thought was attractive would express that they also found me attractive. That being said, the hangups that plague us at a young age often stay with us for a long time, even if life experience and self-reflection have both taught us that those hangups are unhelpful and based on falsehoods. ![]() Not only do personalities matter as much as, or more than, looks for many people, but it turns out that plenty of folks actually think I’m hot and pretty. ![]() Of course, I grew up and discovered that the reality of dating was a bit different than I’d been led to believe. Popular media had hammered home the idea for me that appearances mattered more than anything else, and I considered myself to have a mediocre face and a mediocre body at best, so it seemed impossible that I would ever be loved or desired in the ways I wanted to be. One of my biggest fears, when I was growing up, was that no romantic prospect would ever be able to see past my looks and love me for my personality. Pictured in November 2017, during my very brief foray into sugar dating
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