How I overcame my crushing loneliness by dating grumpy old men
When I was 18, I worked as a barista in a small coffee shop. During the day, I would attend class for my Broadcast Journalism degree; and at night, I would live the life of any teenage college student … I would drink cheap beer until I felt on top of the world.
One very hungover Saturday morning in the Fall of 2013, after serving who knows how many cups of gourmet coffee to strangers, my favorite regular came in.
“Wow” he exclaimed, “You are beautiful!”
This kind of took me by surprise, as I had been serving this gentleman coffee for the past few weeks and he had never even taken a second look at me.
All I could say back was “Thanks! I really needed that today.” He slid his bill across the counter under my fingers. “Keep the change,” he said, and walked off with a smile. I took the bill off the counter and realized he had given me three 20s and one 10 for a $3.90 coffee. I thought it must have been a mistake, but he had already gone.
When my shift was almost over, The Gentleman showed up again, but didn’t approach the counter. Instead, he waved me over. He then handed me another $80 and a lottery ticket, saying, “I hope this makes you as lucky as I’ve been meeting you today.” Nope, not a mistake.
The next day, he gave me a couple more 20s and asked me to take my break to sit with him.
I sat in a booth with him for half an hour, listening to how he had just separated from his wife, that he was sad and lost, and had not looked at a woman in years … until me.
I sat, nodding and empathizing with this sad man. At the end of my break, he slid a piece of paper under my hand and told me that should I ever feel the urge, to text him, as he could use the company.
After a couple of days of texting The Gentleman, I arranged to meet him on a Tuesday evening. I somehow knew I should dress up. I wore a skin tight black dress with nude heels and my hair in waves falling down my exposed back.
He picked me up in his black Cadillac SUV. He stared at me, jaw open and gaze fixed on my blue eyes. He seemed to snap out of it quickly, apologized for staring and saying sorry for his “soccer mom car,” but admitted that I would look good driving it, so offered me the driver’s seat.
This was the first time I had been in a Cadillac, let alone driven one. I felt like a rock star in that seat, and the glamour only continued. We went to a fancy restaurant, where well-dressed middle-aged women with their husbands in suits, chatted about their days over martinis.
I didn’t belong here, but I must admit, I did look the part. The Gentleman told me to order whatever I liked. I decided to test the waters and looked for the most expensive drink.
When I ordered, The Gentleman looked at me and said, “Get something else too. It’s nice to have a variety.” And so I did. The night continued like this. We ordered food, wine, martinis, margaritas, beer, and by the time we were ready for the bill, my head was swimming.
I was laughing genuinely, explaining my life in great detail and enjoying the fact that he couldn’t take his eyes off me.
At the end of the night, he thanked me for a lovely evening, hugged me across the console and slid a bundle of bills into my hand, telling me not to object. When I got into my room, I opened my hand to find a total of $400 in it. This man, this stranger, had just paid for a $200 food tab, and given me that much money in cash, just for spending time with him.
I met with The Gentleman many times over the course of my schooling, generally two or three times a week, and each time he would let me drive his Cadillac, treat me to whatever I wanted, and at the end of the night, would always hand me a roll of bills always ranging between $300-$600, saying, “That’s all the money I have in the world, and it’s yours.” I knew that was a lie.
After about six months of meetings, he began giving me a weekly allowance, and his Cadillac whenever I wanted it. I would drive to school, I would go on trips to visit my friends and family, and I would use his Cadillac and MasterCard to do it.
Many dates, many drinks, and many pairs of shoes later, The Gentleman offered to pay for a townhouse for me so I would have more privacy, and so he would know that I was safe. It was only a few months after I had moved in that, without a real job, and just relying on his word to pay for rent, hydro, my phone and spending money, that I was brought back to reality. I couldn’t put my finances, and therefore my life and security, in the hands of this man.
I moved out of the townhouse, but The Gentleman would not mark the end of my career as a Sugar Baby. After all, at the age of 22, when you’re on your own, attractive, bright-eyed and bushy tailed, what’s stopping you from taking a step outside the box, and putting a value on the most valuable thing you possess? That thing is you.
After hearing about the website SeekingArrangement.com through a friend, I tried to wrap my head around the thought of actually intentionally meeting men who would pay for my attention. In 2015, I logged on for the very first time. It’s there I found the bigamist perversion I knew I would see, but I also found an opportunity.
For the sake of this article, let us call this next suitor Professor X.
Professor X messaged me one cold evening in November. After reading his profile, looking at a couple pictures and shooting him a text (or 10), I decided I would like to meet him. I was informed that I should always make an arrangement that is suitable and safe for both parties involved. I decided to see how much I was worth in the first meeting, and informed Professor X that I would only meet him if he gave me $250 cash, plus paid for my meal, as well as cab fare both to and from home. He eagerly agreed.
When the night finally came, I was so scared, that I was fucking shaking. But I honestly did need the money and was doing something that made my adrenaline skyrocket, so I was willing to accept the consequences, if any.
My cab pulled up to a posh hotel downtown. As I walked through the doors, I thought for sure someone was going to know what I was there for.
Despite the nerves, shame and undeniable excitement I had flowing through me, I channeled my inner Julia Roberts (yes, that was a Pretty Woman reference), and walked into the restaurant.
Professor X walked right up to me, slid one hand around my waist, and planted a very French (and very affectionate) peck on my cheek.
After a lovely dinner, a couple drinks and a very forced conversation about who he was and why his relationship wasn’t working with his wife (men always want to talk about this), he invited me back to my hotel room, claiming the money for me was left there. Although this seemed like the start to a very bad ending to the night, I agreed.
As we made our way up the elevator, he turned to me, and before I knew what was happening, his mouth was clumsily on mine. In shock, I stood dumbfounded as he fumbled his tongue around inside my mouth, and before I could come up for air, the ding indicated we were on his floor. Not a word was spoken between us as we walked to his room, my fist clenched in his palm.
I began shaking as I quickly realized I should probably just turn and run, but for some reason, I walked through the doorway. I sat nervously on the couch in his gorgeous suite, twirling my hair and giving him a smile as he poured me a glass of champagne. The bubbles were smooth as they made their way down my throat — I couldn’t seem to catch my breath.
He then asked me, very abruptly, what my price was.
This question seemed to rattle me … I wasn’t for sale … or was I? Knowing all too well that I did not want him to put his grubby paws on me again, I decided to step outside of my comfort zone and see what I could get for something that didn’t involve intimacy.
I offered to go into the jacuzzi with him, if he paid me another $400. I explained that I wanted us to get to know each other better before I would trust being intimate with him. This was a lie. I knew I would never see him again.
This lie put a big smile on his face. He agreed to my terms and began to undress himself. There, naked, exposed and beyond vulnerable, I sat in that tub, talking about what he believed was attractive in a woman. I listened, counting down the minutes until I could get out of there.
At long last, we got out, dried off, and as I put on my bra, he threw a wad of cash on the bed. I thanked him, gathered the money, gave him a hug and left the hotel, dignity wavering.
I grabbed a taxi outside of the hotel, and as I chatted with the driver, he asked if I was at a business meeting, since I was so dressed up. “Yes,” I lied. I put in my headphones and fell into the rhythm of my breathing. I was okay.
After making over $600 in three hours, I quickly realized that this was a give and take business. I felt sick for what I had done, but was proud of myself for being able to stick with the experience. It was unlike anything I had ever imagined, being with a man who wanted to pay for my company. I was scared like hell, but it sure beat putting on that black outfit to sell jewelry to people with too much money.
You may be asking yourself, why would I put myself through that, even for the money?
The answer is simple; I did it once, I did it twice, and I did it more than that because was looking for an escape.
Let me be honest with you; the first night I texted Professor X, I was alone in my tiny attic apartment that smelt like dust, wrapped in blankets because my heat had stopped working and sniffling into my cat’s fur after a good cry session.
This girl who was in shambles — this sad, lonely girl — existed for a long time before I started working as a Sugar Baby. I have always thought that my life should be anything but ordinary, and for the few times that I met with various men from that site, I felt like I was living a life that wasn’t mine. I’m not saying that being a Sugar Baby made me feel happy, but for those few hours, spending time with men I didn’t even know, I didn’t care about anything else. I felt free.
And that was worth more than any price tag.
Over the years of my young adult life, my work as a Sugar Baby has taught me something indelible about myself: what it feels like to stand on my own two feet. I loved, and my God, I have lost, but after all this, all the good and the bad, I’ve found comfort in myself when times get lonely. And I will always be there for those who are feeling the same.