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While exploring that question, I came across Seeking Arrangement.com, a website designed to pair sugar babies with sugar daddies or mommas.
Now here was something different; something I never, ever thought I would discover. But a part of me was very curious — too curious to ignore.
He'd laid all his cards on the table, and I was either in or out.
Oddly enough, he never asked if I had children and I don't remember ever bringing mine up.
It was pretty uncomfortable at first, since he showed up wearing a suit and asked very non-personal questions about my life.
"Tell me a little bit more about yourself," and, "What have you learned from your past relationships? It felt more like a job interview than a date, and there were no fireworks exploding like I had hoped.
Not when I was 21, and certainly not as a 51-year-old divorced parent of three.
Foreplay felt like a chore, and eventually we weren't having sex at all.
I learned that he had two children and was separated, largely because he and his wife weren't intimate enough. He was looking for someone who was sexy, confident and stable, which he wasn't finding by dating younger women. After my past experience with the 29-year-old, I was worried that he might not be on my maturity level.
But the way he spoke about his career and what he wanted out of our arrangement told me there were no nasty tricks up his sleeve.
) and it was impossible to get a sense of what these men were about.
After one too many failed dates, I seriously considered starting my own dating site. Business idea: How could I make this more enjoyable for women, so they can weed out the bad eggs before suffering through a terrible date?