Being a successful woman today is hard. Being a successful woman who is also a lesbian is even harder. People make wild assumptions about you, they discriminate against you. Some have even claimed that I’ve only gotten to where I am because people feel they need to promote someone who is homosexual so they do not look like they discriminate. You’d think by now people would be more open and understanding to the homosexual community considering it has become such a thriving and vibrant community all over North America. Private Arrangements was a blessing in disguise.
Dating in the lesbian community is tough too. Especially with the younger crowd. Often times they end up just being bisexual and going for someone their own age or finding a boyfriend. This is where I began to grow tired of the dating scene. I wanted to be with someone but I was sick of weeding through the girls who were ‘experimenting’ or ‘figuring things out’. I’m old enough now to know what I want and it seems like the ones I want re long taken by someone else.
On a whim, I decided to try sugar momma dating. While Tinder and Plenty Of Fish seemed like the obvious choices, they were just filled with more of the same. Then I came across, Private Arrangements for seeking private arrangements. A dating website that specialized in helping someone like me, rich and successful find mutually beneficial hookups. I decided to try it out for the 30-day trial. What was the harm, right? I made a sugar momma dating profile, uploaded some cute photos of me and made it known that I have a high income net worth and do not mind spoiling someone special.
I got a few messages my first week of being on there. A couple of girls who were a little bit younger than me. One who was still in college, in fact. I decided to give it a shot and meet them in person.
*All names have been changed for the sake of their privacy.
Melanie, a local small business owner on the East End. Late 20’s, appeared to have a great personality was the first one I met up with. We met at a bar uptown that had a great selection of imported beers from around the world. I got there early and took a seat at the bar. She showed up almost 20 minutes after our agreed upon meeting time and claimed the cab driver took her to the wrong place. Understandable mistake. She looked exactly like she did in her photos, which was great. I’ve heard way too many horror stories of meeting up with someone and it turns out they look nothing like their profiles.
I asked her what kind of business she owned. She went into fully detail about she ran a dog grooming business, but because the neighborhood was going co-op, she couldn’t afford to make ends meet as well as she used to. (Might I add she downed two drinks during this sob story speech.) She wasn’t as charming as she had seemed online. When she finally stopped talking about her failing business, she asked what I did. I told her I was a corporate lawyer for one of the top firms in the city. She immediately began to ask me questions about if she could use my law experience to help her business out.
At this point, it became quite clear that she was only interested in getting free legal advice and wanted money. Still, being the forever optimist, I paid for our drinks at the end of the night and asked if she wanted to keep this going and maybe grab a night cap at my place. She said yes and my driver took us back to my apartment. We sat in silence in the car ride. Very unpleasant. I tried to hold her hand, but she just flinched and readjusted herself in her seat.
We got to my place and basically all she could talk about was how rich I was. I get that not everyone lives the life I do, being a multi millionaire, but have some class. I offered her a Scotch and we sat on my couch and kept talking. I leaned in to try and kiss her and she pulled away and stated "Not before we go over the details of what this could be."This was a major turn off. I asked her what she meant. She explained to me that she wanted to be compensated a certain amount for anything even remotely sexual. She was even very specific about the price. I had never felt more used and humiliated. When I asked her to leave she replied with "please you knew what this was."I honestly hadn’t. I was looking for something deeper. I didn’t want to feel like I was just some ATM . I didn’t want a prostitute.
After that horrible night I decided to give it the site another chance. I checked out some of the blogs about my situation on the side and new I could do this. I was seeking private arrangements. We have all been on bad dates. It wasn’t the site’s fault. After another week, I decided that I could use something a bit fun to get me out of this funk I was in. I messaged the college girl and asked if she wanted to grab dinner. She quickly agreed with a little smiley face emoji. College girls are so cute. I didn’t know what I was expecting but I was just seeking private arrangement.
We met up the next night at this cute Italian restaurant in the Village. She was waiting when I got there and gave me a big hug when I stepped up to meet her. She opened the conversation up with "I took the liberty of ordering us Sangria, I figured if you didn’t show, I’d twice the drinks." She had a great smile and already seemed super fun to hang out with. The drinks came and she paid the bartender for them both and we took our seats at this cosy booth in the back. As we browsed the menu, she couldn’t decided what she wanted to eat and asked what I was having. Turns out we were debating over the same meals. Already a good sign to me. We agreed to get them both and share. My first thought was "I could totally have my Lady and Tramp moment with her." As childish as it seemed, it was a good feeling. I asked her about her schooling and it turns out she was in medical school training to be a doctor. This was another great sign, she had a great career path in mind.
"I’m not overly rich, I’m living off a lot of student loans but I work a number of jobs to help me be able to have a bit more of an income." She confided to me. "But please do not think that’s why you are here. You seemed like someone I could connect with, that’s why I messaged you in the first place." This actually warmed my heart. I asked her all about why she wanted to be a doctor and she explained that her mother died of cancer when she was very young and she wanted to help keep up the fight she had lost. I was almost in tears when she pulled up a photo of her and her mother on her phone.
When the food arrived, we both started twirling spaghetti around our forks, or picking up pieces of loose chicken from the penne with our fingers. We joked and laughed. She seemed like a genuinely nice and fun person. I guess with my past experiences, I just assumed she would never be interested in me, but she was. She asked me all about why I wanted to be a lawyer, where I grew up and what my favorite movies were. There were no sob stories about debt. There was no "Let’s talk about our arrangement". There was just a pleasant conversation between two people. When our meal was done, she asked if I wanted to go home with her and open a bottle of wine. Of course, I agreed.
It’s been over a year now and we are still going strong. She’s placed in a great teaching hospital and is working hard at her studies. I asked her to move in with me a few months ago so that she would have a nicer place to live and it was an easier commute for her. It’s been going really great. I honestly never thought I would end up with a college girl, but she was not like all the others. She was funny and smart, completely down to earth and so much more than what I could’ve wanted.
The best part is, she never asks for anything. Not asking for things gets her spoiled way more. I think she knows that, but my money hasn’t affected our relationship. I’ve even made some effort to put a dent in her college debt. It was an anniversary present. We are a team now and that’s what I wanted. She cares for me, she always cooks me dinner when I have to work late on a case and I make sure she has little to no stress in her life so that she can focus on being the great doctor I know she can be.
I have to say that while my experience with online sugar momma dating was sketchy at first. I was thrown off by how awesome it can work if you just stay positive and open minded. There are plenty of motives for someone to become a sugar momma and finding love is one of them. Sign up with Private Arrangements to have the same mutually beneficial connection I have. You won’t be sorry.
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