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(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 $3,500 a month in cash. On that second date, John and I decided to give the sugar daddy-sugar baby thing a go. I knew they weren't ever going to meet him, so I didn't feel the need to tell him right off the bat. At the time, I had joint custody and only saw them two weeks out of the month. Oddly enough, he never asked if I had children and I don't remember ever bringing mine up. He laid all his cards on the table, and I was either in or out. But one thing was for sure: With his dark hair, piercing blue eyes and 6'5" frame, I was definitely attracted to him. It felt more like a job interview than a date, and there were no fireworks exploding like I had hoped. "Tell me a little bit more about yourself," and, "What have you learned from your past relationships?" to name a few. It was pretty uncomfortable at first, since he showed up wearing a suit and asked very non-personal questions about my life.
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I wasn't really sure how to read him, and I'm usually pretty good at that.Īfter some brief small-talk (you know, the typical what-are-your-hobbies-what-are-you-looking-for chitchat), we set up a coffee date. His "Hello" note was very straightforward, even a bit cold. John was a 34-year-old business executive from my town. 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 … would they? Nothing too crazy or screamed, "I'm on here to have reckless sex and get flown to party in Miami Beach every weekend!" I just wanted some casual fun with a classy man who had it together.Īs I finished creating my profile, doubts flooded my mind. I created my profile and uploaded pictures of myself. But a part of me was very curious - too curious to ignore. Now here was something different something I never, ever thought I would discover.
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While exploring that question, I came across, a website designed to pair sugar babies with sugar daddies or mommas. 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? I thought, surely I'm not the only person struggling to find someone. After one too many failed dates, I seriously considered starting my own dating site. The questions were surface-level (like, do you prefer romantic comedies or horror movies?) and it was impossible to get a sense of what these men were about. It seemed like these sites were almost trying to set me up for a disaster. It wasn't just because the men didn't look like their profile pictures. I went on a few dates here and there, but mostly they were just … bad. But OKCupid, eHarmony - none of them felt quite right for me. So, I decided to hop online and window shop. By then, I was 50 with three kids and unwavering aspirations of getting my MBA. As striking as this blonde-hair, blue-eyed guy was, he just wasn't stable enough for me. His easygoing and carefree personality was the polar opposite of my ex. I wanted to take control of my life and smile again.Ī few weeks after signing the divorce papers, I jumped right back into the dating game with a 29-year-old I had met at a work function. After 15 years - six of which involved intensive marriage counseling - I finally decided to walk away. I existed to make dinner for the kids and provide an open ear when he needed to vent. Foreplay felt like a chore, and eventually we weren't having sex at all. But over time, I felt myself becoming more like a nanny and less like his wife. He's an entrepreneur, so I was always sympathetic to the demands of his work. Together, we had three beautiful children and lived the classic, white-picket-fence life for almost two decades.īehind that fence however, I was miserable.
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After a fluke first marriage at 27, I met the successful, headstrong man I was taught to believe every woman wants. After divorcing my husband of more than 15 years, I was single again and ready to have some fun.įor a long time, it did.