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Seeking Private Arrangements : A Single Mother's tale

The thought of seeking private arrangements started as a joke with my friends. It was just one of those jokes that came out over some casual gossiping.

Seeking Private Arrangements: A Single Mother's tale

It was the nicest looking restaurant I had been to in a while. I sat across a man I’d only exchanged a few words with before daring to ask for a face to face meeting in silent awe of the situation. Only a few months prior to this, I would have never imagined this situation. Me, dating again. Let alone dating a potential Sugar Daddy.

To say that I was nervous was an understatement of the century. I’d borrowed some nice clothing from a girlfriend and a pair of classic louboutins. Meanwhile, he wore a clean pressed suit that was probably more expensive than everyone’s bills combined. The man must have been a little over fifty, but was still devilishly handsome. As I relaxed over a drink, the night quickly became engaging and fun. We chatted about many things, mainly philosophies and the state of the world today. Later over dessert, we shared a few laughs over silly things we’d done in our youth and by the end of the night he offered it up.

"I’d like to help you," he said. "$9,000 a month."

Here I was, a single mother with two kids barely able to cover the bills and he just said that he would pay me $9,000 a month to be his companion. $9,000 a month to be the companion for someone who I genuinely enjoyed conversation with and frankly found very attractive. I was floored.

The thought of Seeking Private Arrangements started as a joke with my friends. It was just one of those jokes that came out over some casual gossiping. It was a Friday night, the kids were all tucked in and I had several of my best girlfriends coming over to drink, snack, and get nostalgic over old episodes of FRIENDS with me. Things had been difficult ever since my husband and I had the divorce about a year ago. I had two kids, one aged four and another seven. We had to move into an apartment and I had to pick up a second job to try and cover the costs. The divorce itself wasn’t an easy one and there were still several expenses to cover over the battles that continued to wage on.

Like all girls nights, our chatter and gossip eventually turned to relationships. My oldest girlfriend had been through a similar situation. While she’d never married, her long term partner up and left about two years ago and with that, so did a lot of her security. She had been sound support for me in my trying times.

"You guys won’t believe what happened a couple nights ago," she opened her story with.

As it turned out, my friend had recently gone on a ‘sugar’ date. The man she hooked up with was offering her $6000 a month. Now that was something I could really use.

She stumbled across a site called Private Arrangements geared toward, you guessed it, people seeking private arrangements. Up until that moment, I never dreamed of considering giving the lifestyle a try. I liked to think I wasn’t a prude, but the idea of getting paid for a relationship? It seemed wrong. Still, I had to stop and ask myself why. Why was it wrong to trade money and gifts for companionship and sex when in a way wasn’t that how marriage was long ago anyway? If someone was willing to pay me for my time with them, how could it be all that bad?

You Would Not Believe What I Discovered About Seeking Private Arrangements

So I did some research. To my surprise, the amount of people living in America that are seeking private arrangements is incredible high. Several sugar daddy dating sites have a member pool of 40,000 or more. Thousand upon thousands of women and men are looking for mutually beneficial affairs for themselves. If so many people are enjoying the lifestyle, then why is there such a bit stigma around it? The more I read, the more ridiculous the scrutiny all seemed to me. Not only was the amount of people seeking private arrangements so high, but the kind of men and women that were looking varied to such a great degree, that I actually felt like I might have a running chance.

When you think of a Sugar Baby, what do you think? I always thought of someone young, long blonde hair and blue eyes. Definitely not someone in their early 30’s with two kids and an ex husband. But lo and behold, there were older men: the classic Sugar Daddy. There were young and ambitiously wealthy men interested in finding a Sugar Baby, too. I took a look at the website my friend was talking about, Private Arrangements and found my confidence strengthen even further.

On privatearrangements.com, my mind opened even further. The site was new, which gave fresh opportunities to a smaller pool of people. A smaller pool of people meant the chances of being seen were far greater. I thought, what’s there to lose? I’d have read a couple storied with some gruesome tales. On blog sites, Sugar Babies shared their stories on Sugar Daddies gone wrong, dos and don’ts, and how to spot a fake Daddy. I found so many different types of women seeking private arrangements with sugar daddies. Women of all shapes and sizes. Women of all different ages. There were several blog entries with great tips and tricks and real life advice that helped me understand more about the lifestyle and what I was getting into.

With a deep breath I staved away any cold feet. I needed the money, I had kids to feed and legal bills to pay. I wanted my life back again and if that meant doing a couple favors to get what I want, it wasn’t all that bad, was it? Besides, my friend had a great experience with it. So I signed up. Just like my friend said, filling out the profile was easy. I picked out a couple of recent photos, answered all the basic questions about myself easily, and thought long and hard on whether I wanted to be honest about my situation or not. I figured, why not? Maybe someone nice would come along and understand my needs more for the honesty. So I put it in, mother of two beautiful children.

And I waited…

I had forgotten how gruelling dating was. For some reason, I thought that this might be different. It was online and it was a private arrangement. No strings, right? While I didn’t find my husband through an online dating site, (we were high-school sweethearts) I know several people who had very good luck through online dating. I buckled up and started checking regularly. That’s where my confidence started to fade. The few who did reach out to me didn’t seem like a good match. I thought, was I just this rusty with dating? Was I still afraid to just go for it? Maybe I needed to be less picky? It’s for the money, I reminded myself. So I finally gave a couple people a chance.

The first man I connected through on a site that will remain nameless, let’s call him John, was a bank executive. When I did some research on him, I found out that his estimated annual income was over $57K and I figured someone with that kind of dough could certainly lend a bit to a person in need. He messaged me with a short, ‘I could use someone wholesome on my arm.’ I wasn’t sure if that was a back-handed compliment or he just didn’t understand how to talk to women over twenty-five, but I thought, sure why not? So he invited me to a small Italian bistro and for the most part, the date was alright in the beginning. We got to know each other a little, shared some of our interests over some wine and delicious Carbonara. I thought, if anything, the food was certainly worth it.

Sugar Daddies Are Online Now!

On our second glass of wine, he started talking about what he was looking for. He told me flat out that he was married with children as well, but their sex life had gone flat. I tried to remember the mantra ‘this is for the money,’ but couldn’t help be reminded of my own ex. He said he needed someone a little more mature looking to not cause suspicion and she needed to be sophisticated enough to look like she was a business partner and nothing more. As I listened to him, I thought it sounded reasonable enough that I could manage. Then he laid down the killing detail. Since he was married and had commitments, he would prefer their arrangement be pay per meeting.

I thanked him for the meal and ensured him that it wouldn’t work out between us. I had half the mind to tell him to talk to his wife about their sex life, but I managed to refrain and left shortly after. I could tolerate sex being part of the deal, I even expected it, but I was not a hooker. So back to one I went.

There were several busts after that. One man was completely different than the description he gave in his profile. Another man was crude, rude, and clearly not worth the effort. Then came George from Private Arrangements, the man I started talking about earlier. Smooth, charming, handsome. When I first met George, I had become a little bitter about the whole experience, but through out online conversations, I started to grow a fondness for him. By the time we met, I was nervous and legitimately wanted to impress him (enough to borrow some of my friend’s clothing).

He was an exceptional gentleman, happy to hear my terms and was very clear with his own. I am glad to say I have been in this private arrangement for several months now and my life has become so much more freeing and comfortable. For those of you Seeking Private Arrangements, don’t give up! There IS someone out there for you, I promise. I found mine. You WILL find yours.

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