Three sips into his first cup, he began opening up about his personal life.
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.
As I finished creating my profile, doubts flooded my mind. While scrolling through the site a few days later, a man, John,* messaged me out of the blue.
No one would ever seek out a 50-year-old sugar baby … John was a 34-year-old business executive from my town.
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.
I created my profile and uploaded pictures of myself.
After one too many failed dates, I seriously considered starting my own dating site.
After accepting, I was relieved when he pulled up sporting more casual clothes this time.After some brief small-talk (you know, the typical what-are-your-hobbies-what-are-you-looking-for chitchat), we set up a coffee date.It was pretty uncomfortable at first, since he showed up wearing a suit and asked very non-personal questions about my life.Perhaps it was my Roman Catholic background that shaped my views on relationships and love, but I used to think the sugar-daddy-sugar baby dynamic was silly and taboo.That kind of relationship didn't go with my moral standards. After a fluke first marriage at 27, I met the successful, headstrong man I was taught to believe every woman wants.