“I Date Sugar Daddies—And Here’s Why I Love It”
By Wendi Starling; photograph by Unsplash
“We laugh loudly, kiss deeply, dance off beat, and hold hands while we sleep, but we never mistake that for love.”
The first time I dated a sugar daddy, it happened very organically. I met him in an exclusive club in Hollywood, California, when I was 19 years old and impressionable. This gorgeous older man approached me and said, “You’re beautiful. Do people always tell you you’re beautiful?” My first instinct was to say, “No. Go away, please.” But I decided to play coy and said, “Yes. I hear that all the time. Tell me something new.” And then he kissed me.
At that point in my life, I had only been intimate with one boy, and this adult man was my second. We dated for a few months, and then it became difficult to see each other because I took a second job as a server in a nightclub to pay my bills. After a few weeks of not seeing each other, he asked me if I was blowing him off to see other guys, and I assured him it was only due to my new job. That’s when he offered to pay me what I was making at that job in order to spend time with me.
For the next eight months, he paid my rent in addition to mini shopping sprees. He also covered our fancy dinners. We almost always sat at some VIP secluded table in the back. He treated me like a precious doll.
Our entire relationship was like a dream until one night at dinner he told me he was married. I felt nauseous. The room spun. I wanted to scream at him, but I could only ask why he was even dating me. He said, “I like you,” while staring into my eyes and reaching for my hand. I pulled away and said, “Take me home please.” We broke up after that.
Fourteen years later, I moved to New York City to pursue stand-up comedy and needed to come up with an additional $1,500 for rent because a roommate bailed at the last minute. I panicked. Even working 50 hours a week at my day job wouldn’t cover the unexpected expense, so I delved into the dark underbelly of the Craiglist ‘Gigs’ section with the hopes of finding a get-money-now solution.
I responded to multiple ads looking for “massage girls” and “elite” escort services, but the few responses I got were super-shady-sounding, so I followed my gut and never actually met up with any of the Craigslist people. While performing at a comedy show later that week, I was ranting about my potential foray into sex work (I tend to talk out the majority of my struggles and hardships through comedy). Afterwards, a friend told me about a few different sugar daddy websites, where you could sign up to meet men who were willing to pay for your lifestyle.
Thanks to modern technology, I was able to sign up right there on the street at 3 a.m. If I’m being completely honest, I was pretty drunk when I filled out my profiles and did it mostly as a joke, but I did it.
Then I dragged myself home, passed out, and kinda forgot about it until the messages started rolling in. Most of the messages were along the lines of “How much per hour?” which I totally get. I’m not naive to (or judgemental of) the fact that these sites can be used as a legal loophole for men to connect with escorts, I just wasn’t comfortable meeting in an hourly hotel for a couple hundred bucks.
Thankfully, I booked a last-minute stand-up gig that paid $1,800, so I was able to cover my extra rent. After eight or nine months on the site, I never met up with anyone. At that point, I stopped checking the website entirely.
But then I started receiving new messages. These men were not asking about an hourly rate, they asked me to describe my ideal evening out in the city. They were even attempting to make little jokes. So I responded and got a few separate chats going; I started to think of it like a “normal” dating site. And aside from the discussion of my allowance and their expectations of our time together, it’s pretty much the same as any other dating site.
In fact, I found the conversations with potential daddies to be more straightforward and honest than almost any I’d had on traditional sites—or even second dates in real life. It was refreshing to be completely open with potential partners. These guys are just looking for the excitement of having a fun girlfriend without emotional entanglements, and they have the expendable cash to help that girlfriend out with some bills in exchange for not blowing up his phone at 3 a.m. or asking, “Where do you see us in five years?”—and for always being ready to jump in the sack. And lucky for me, I am always down to get down, so that was not a chore.
Anyway, after chatting with a couple of different guys, I felt ready to go on a actual date. But that’s where it got tricky. When I meet a guy under circumstances like Tinder or (gasp!) just going out and talking to some guy at a bar, it is not out of the realm of possibility that I will either go home with him or bring him home with me. But on a date with a sugar daddy, I knew I’d have to focus and stay sober, because it’s as much a job interview as a date. And in the event that we liked each other and wanted to hook up, there had to be an agreed-upon allowance and money had to change hands.
On my way to my first date through the site, I remember fear and paranoia taking over my body. Up until this point, I had only chatted with the guys via the dating site. I had never knowingly gone on a first date with a guy I knew would be paying me for the pleasure of my company. I thought, “Is this prostitution? What if there is a genuine connection? What if it turns out to be just a one-night stand? Would it be different if, instead of placing the money directly into my purse, he spent that money on an evening at the theatre, followed by an extravagant dining experience? My heart was pounding the entire train ride. And then it was my stop.
I had no idea what to expect when I walked into the restaurant. Part of me was afraid the whole thing was an undercover sting operation, and I would be tackled and arrested immediately upon entering the building. But I walked through the bar almost completely unnoticed and was pleasantly surprised to see the same handsome man from the the photos online stand to greet me as I approached the couch he had secured in the lounge.
From that point forward, it was just like a normal date. Perhaps even more relaxed than most first dates because we had already established our needs and expectations. We knew that if we were both in the mood, sex was absolutely going to be part of the evening. And, as luck would have it, we were both very much attracted to each other, so we headed back to his place for intensely passionate love-making followed by what I can only describe as him worshiping my body while we fell asleep.
We woke up wrapped in each other’s arms and lazily rose to get ready for the day. He made coffee, sliced up an apple; it felt like we were playing house. After breakfast, I jumped in the shower, rushed to get dressed and make it to work on time. When I grabbed my purse, I noticed a white envelope sticking out of the side pouch. I made sure I was alone in the room before I opened it to see if it was what I had so masterfully avoided asking about since the second I woke up in his bed. And it was. He had discreetly placed my allowance in an unmarked envelope and snuck it into my purse while I wasn’t there.
I shoved the envelope deep into my purse for safekeeping and bounced toward the front door where he was waiting to give me a kiss before we walked out together. Once on the street, we kissed again and parted ways. He and I continued to see each other ab out once a week for the next three months, and then we called it quits due to scheduling conflicts.
After that relationship ended, I left my profile up on the sugar-daddy sites and had a few dates here and there (for which I would sometimes be compensated without having to do anything more than have a conversation and a cocktail). But nothing went further than that until about four months ago.
I made plans to meet a guy from one of the sites for a drink in between my shows, and we had instant chemistry; I was actually bummed that I only had an hour to spend with him that night. He asked me to stay for a second drink, saying, “Come on, it’s only 20 minutes in a cab to your show.” At which point I reminded him that I did not have cab money and my commute by train was an hour, so I regrettably had to leave. Then he pulled out $100 and said, “Here, cab fare. Same drink?” We finished our drinks then walked hand-in-hand to the street where he hailed a cab for me and kissed me before I sped away to the show. He texted me for the next couple of hours, saying he needed to see me that night. The feeling was more than mutual, so I allowed him to send a car to pick me up in Brooklyn and whisk me back to his place in the city at 1 a.m.
Our time together was magical. When his alarm blared at 6:45 a.m., my head was still swimming in white wine. He jumped up, readied himself for work, and then came back into the bedroom and kissed my forehead. “I’ll be dressed and ready to head home in 10 minutes,” I said. “Shh. Babe,” he whispered, “just sleep in. Help yourself to coffee and food downstairs, and I’ll talk to you later today.” He tiptoed out and gingerly closed the sound-proof bedroom door.
Within the first two weeks of dating, he bought me an Equinox membership, an espresso machine, and the new iPhone 7—and he funded general shopping trips and offered to pay for car service when I have an especially busy day. Within the first two weeks of dating, he bought me an Equinox membership, an espresso machine, and the new iPhone 7—and he funded general shopping trips and offered to pay for car service when I have an especially busy day.
Sometimes, we’ll go out and drop $500 on lunch in Soho. Other times, we just order in and dance around the kitchen blasting Fleetwood Mac. We genuinely like spending time together. He has come out to my shows, and I go out with his friends, but we maintain our boundaries, which is what makes the relationship so enjoyable. It may sound strange, but in a normal relationship, if you don’t hear from your partner for a few days, that’s a fight. We don’t have that. Most people (especially in their thirties and older) are constantly assessing the final destination or goal of the relationship. We don’t do that. Rules and expectations are set and respected, which gives us the freedom to go all in and behave as though we are the leads in a classic tale of romance. We laugh loudly, kiss deeply, dance off-beat, and hold hands while we sleep, but we never mistake that for love.
We see each other between three and eight times a month, and he has given me his blessing to date non-sugar daddies outside of our relationship, but honestly, I don’t have the time or energy. As of right now, I have a laser-sharp focus on my career, and thanks to his help, I am able to dedicate more time to writing, running around to shows, and other creative endeavours that will hopefully lead to me being able to afford my own Equinox membership. With him, I also get the benefit of escaping to a world where I can revel in the fantasy of having a boyfriend without the daily obligations of a standard relationship.
I understand that this type of relationship is repulsive to some people, but I can say with absolute certainty that these relationships make me feel valued on every level. Dating men of such high caliber has done wonders for my self esteem. Not only are they proud to be seen publicly with a mouthy comedian, but they actually compensate me for my time and companionship. These are successful businessmen that let me pick their brains about everything from the stock market to their motivational mantras. It sounds cheesy, but being around winners makes me feel like a winner and my behaviour adapts accordingly. Dating these men has forced me to more aggressively chase and achieve my goals. And I gotta say, it feels pretty great to be dating a guy that isn’t threatened by my desire and drive for success—it’s quite the opposite.
In fact, my sugar daddy recently gave me access to his lawyers to make sure I don’t get screwed out of money on a couple of projects. He wants me to succeed. He is a friend, a lover, and a mentor. It’s definitely not the ideal situation if a person is looking for marriage or to start a family, but it works for me. For now.
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