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On that second date, John and I decided to give the sugar daddy-sugar baby thing a go.

(Or, "cougar baby," I guess it's called, since I'm older than him.) I told him what my car payment, rent and living expenses were, and he agreed to give me ,500 a month in cash. We were on the same page from the start, which made things easy.

" I just wanted some casual fun with a classy man who had it together.

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.

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.

I created my profile and uploaded pictures of myself.

Nothing too crazy or screamed, "I'm on here to have reckless sex and get flown to party in Miami Beach every weekend!

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.

At the time, I had joint custody and only saw them two weeks out of the month.

I knew they weren't ever going to meet him, so I didn't feel the need to tell him right off the bat.

) 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?




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