I never thought I would be a sugar baby.
Not when I was 21, and certainly not as a 51-year-old divorced parent of three.
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. Women strutting for a wad of cash and to please a wealthy man … no, thank you. I saw my love life going in a much different direction. The “normal” direction, so to speak.
After divorcing my husband of more than 15 years, I was single again and ready to have some fun.Advertisement – Continue Reading Below
For a long time, it did. After a fluke first marriage at 27, I met the successful, headstrong man I was taught to believe every woman wants. Together, we had three beautiful children and lived the classic, white-picket-fence life for almost two decades.
Behind that fence; however, I was miserable. He’s an entrepreneur, so I was always sympathetic to the demands of his work. But over time, I felt myself becoming more like a nanny and less like his wife. Foreplay felt like a chore, and eventually we weren’t having sex at all. I existed to make dinner for the kids and provide an open ear when he needed to vent. After 15 years — six of which involved intensive marriage counseling — I finally decided to walk away. I wanted to take control of my life and smile again.
A 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. His easygoing and carefree personality was the polar opposite of my ex. It didn’t bother me that he was younger. I was just anxious to feel wanted again.
I wanted to take control of my life.
Our fling didn’t last long. As striking as this blonde-hair, blue-eyed guy was, he just wasn’t stable enough for me. By then, I was 50 with three kids and unwavering aspirations of getting my MBA. I didn’t have time to play babysitter.
So, I decided to hop online and window shop. But OKCupid, eHarmony — none of them felt quite right for me. I went on a few dates here and there, but mostly they were just … bad. It wasn’t just because the men didn’t look like their profile pictures. It seemed like these sites were almost trying to set me up for a disaster. 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. After one too many failed dates, I seriously considered starting my own dating site. I thought, surely I’m not the only person struggling to find someone. 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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While exploring that question, I came across SeekingArrangement.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. At first, I was turned off by the idea. But a part of me was very curious — too curious to ignore.
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!” I just wanted some casual fun with a classy man who had it together.
As I finished creating my profile, doubts flooded my mind. No one would ever seek out a 50-year-old sugar baby … would they?
Turns out, I was dead wrong. While scrolling through the site a few days later, a man, John,* messaged me out of the blue. John was a 34-year-old business executive from my town. His “Hello” note was very straightforward, even a bit cold. I wasn’t really sure how to read him, and I’m usually pretty good at that.
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. “Tell me a little bit more about yourself,” and, “What have you learned from your past relationships?” to name a few. It felt more like a job interview than a date, and there were no fireworks exploding like I had hoped. But one thing was for sure: With his dark hair, piercing blue eyes and 6’5″ frame, I was definitely attracted to him.
My sugar baby gave me $3,500 a month in cash, plus an extra $500 here and there.Advertisement – Continue Reading Below
Given the very proper, business-like nature of our first date, I was caught off-guard when he asked me to go get breakfast a couple of days later. After accepting, I was relieved when he pulled up sporting more casual clothes this time. 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. That, of course, hit a nerve. He was looking for someone who was sexy, confident and stable, which he wasn’t finding by dating younger women. So, he had messaged me.
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. He’d laid all his cards on the table, and I was either in or out.
He 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. 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.
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 $3,500 a month in cash. Now that I think of it, he threw in an extra $500 every now and again — you know, just to be nice.
Was it weird at the beginning? Not at all. We were on the same page from the start, which made things easy. It wasn’t about neon-colored Camaros, colossal diamonds or nights at five-star hotel suites. He drove a high-end import car, but it wasn’t fiery red. His suits were tailor-made, but his sleeves were often casually rolled up. He was worldly, but his small-town roots meant he never looked down on the locals in our town. Not the kind of sugar daddy I had ever expected to meet, but exactly the kind of sugar daddy I wanted.
About twice a month, John would take me out to get French food at a local eatery and we’d sit there flirting and laughing over bottles of wine for hours. Other times, we would go relax at his condo and sit on his couch and talk — no topic, big or small, was off the table. We’d sometimes have sex if we were both in the mood. He never made me feel like I had to please him, though. In fact, he was shy around me at first. But once we discovered our chemistry, our arrangement became more like a relationship. And six months into it, I fell for him.
I was upset with myself for feeling that way. I didn’t want to be serious with someone 15 years younger than me — that just wasn’t the plan. I had joined Seeking Arrangement as a harmless way to have a little fun and explore a possible business venture, not for love.
What’s worse is that right as I started to develop real feelings for him, John fell ill. The market in our town was plummeting, which meant he had to work extra-long hours at the office. The stress of his job led to him skipping meals and losing energy to do anything besides worry. I did what I could to comfort him, but he just kept getting thinner and thinner. A month after his health took a dive for the worse, he texted me to meet at his condo. And when we did, John broke off the arrangement and said he needed to focus on getting better. I left his condo crying that night, knowing that it would be the last time I ever saw him.
Today, I have no regrets about my relationship with John.
Looking back, I have no regrets. Our arrangement only lasted eight months, but I learned a lot about expectations and dating — yes, even at 51 years old. I can think I know exactly what I want (like, someone closer to my age bracket), but the reality is that your desires change once you meet someone you really connect with. And there’s nothing wrong with that. I’ll always have a “type” of man I believe I should be with, but trying to make your relationship — or “arrangement”— into what others want for you and your life is pointless. Who cares if they’re 54 or 34: If you like them, see where it goes and just enjoy the whirlwind of it all.
As for me, I’m keeping my profile on Seeking Arrangement just in case something great comes along again. For now, I’m really focusing on spending time with my teenagers and finishing up my MBA. Sure, it would be nice to find a long-term relationship one day. But if it doesn’t work out, I’ll be fine. I like where my life is headed. There may not be any white picket fences in my future, and I’m perfectly okay with that.
*Name has been changed.
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