Stuck in a jobless and relationship-less rut during the pandemic, a fresh graduate from Singapore was interested in finding alternative ways to make some money. After the city’s circuit breaker period, she decided to dabble in sugar dating to fund her living expenses. 

I was hanging out with a couple of girlfriends when one of them casually joked, “I think you need a sugar daddy.” Ordinarily, I would have dismissed her suggestion. But I had recently graduated from university and the COVID-19 pandemic made it impossible for me to get a job anywhere. Exasperated and desperate to find a way to make some money, what started off as a joke got me thinking about giving Seeking Arrangement (SA), a sugar dating site, a try. Furthermore, I was fresh off a breakup with my boyfriend of four years and the idea of getting paid to go on dates sounded pretty appealing. 

Creating a Sugar Baby Profile

When I first got on the site, I was prompted to sign up with an education email address (.edu) in order to get more “perks”. The registration process felt like a resume, except I had to fill in my ethnicity, height, and describe my body type (there was even an option titled, “a few extra pounds”). The site also prompted me to indicate my expectations with categorical options that included “romance”, “long-term”, “discretion”, “intimacy” and “no strings attached”. I uploaded a single picture of myself at the beach. I chose a silhouette photo to remain anonymous at that point. After all, I was still a little apprehensive and didn’t know what to think of myself for actually considering a sugar daddy. 

Once my profile was ready, approximately five to six sugar daddies reached out to me within minutes. Around 30 sugar daddies reached out to me by the end of the day. The amount of attention I received on Seeking Arrangement was a little startling because on other online dating sites, such as Coffee Meets Bagel or Tinder, it would take more than a day to match with 30 different people, much less start a conversation. Just like Tinder, the messages I had received ranged from polite to lewd. Some men straight-up offered 200 to 300 bucks for a one-time sexual encounter. Others introduced themselves and tried to strike up a conversation without bringing up the transactional nature of the dating site. One man offered me SGD 4,000 per month to go on dates and have sexual relations with him. I would only have to meet him once a week and he promised to pamper me with lavish date nights and gifts, on top of the monthly allowance. Another offered me SGD 600 to act as his girlfriend and go out with him two Friday nights a month, without any sexual relations. 

I found myself drawn to a 27-year-old man, Timothy*, whose bio stated, “I’ll be the best boyfriend you’ve ever had”. He caught my eye as he had set up his Seeking Arrangement profile the way one would set up a Tinder profile. He was looking for a long-term, romantic arrangement. Timothy texted me with a quick and simple, “How are you doing?” Then, he started asking me about myself and why I was on SA. We had good banter, and good conversation and his profile picture on SA was pretty attractive. “I could actually do this,” I thought. He asked me how much allowance I needed. While I really had no idea since I had never been someone’s sugar baby before, I told him I’d be good with somewhere between SGD 2,500 to SGD 3,000 a month. That would be sufficient for me to get by since that was the range of how much I can earn as a fresh graduate. Eager to test our chemistry, we made plans to meet for dinner the following night. 

*name changed

The Fateful Date

I arranged to meet Timothy in the well-lit Central mall at Clarke Quay. After reading Seeking Arrangement stories, I wanted to be cautious about meeting someone who might put me in a dangerous situation. Most of these stories were based in the United States but considering it was my first time meeting someone through the site, I preferred to err on the side of caution. I was actually as excited as I usually would be on a first date because I was particularly intrigued by why this 27-year-old who was relatively good-looking was on SA as a sugar daddy. “I would’ve swiped right on this profile if it was on Tinder”, I thought.

I waited by the elevator until a man came up and approached me. “Timothy?” I asked and smiled through my mask, before proceeding to give him a quick hug. He looked different from his profile picture — he had gained a few pounds and had a little pot belly. To be fair, he had given me a little heads-up saying that the photo was taken a couple of years back, so he probably didn’t plan on “catfishing” me. I just didn’t expect him to look this different. We headed into the restaurant and I finally saw him face to face without our masks on when the food arrived. When he took off his glasses for the meal, he looked a little more like the guy in his profile picture. While we made our way up to the restaurant, I could tell that he was a little awkward but extremely respectful and gentlemanly. We made small talk and I felt relatively comfortable with him. 

Over dinner, we shared our dating experiences candidly. I liked Timothy from the very start because he was genuinely interested in engaging in honest conversations with me. He said that he used Seeking Arrangement because he knew that the girls on the platform were not keen on wasting time. He also admitted that sugar dating allowed him to get the company of girls who were way prettier and hotter than those he could usually score on Tinder. 

When he picked up the check after dinner, I offered to split it with him, as I usually would on any other date. He shot me a really confused look, which seemed to say, “was this chick actually asking if I wanted to split the check with her when she’s trying to be a sugar baby?” I immediately realized that that made me look totally inexperienced and so I looked away while he paid. We walked over to Clarke Quay for drinks after dinner and he bought both of us a double Macallan 21 on the rocks. 

While Timothy didn’t look like his profile picture, I genuinely enjoyed my date with him. After all, he was everything he said he was — a hopeless romantic who was looking for love in a world where people often couldn’t look beyond the physical and material. He wasn’t the rich, douchey old man that I had originally expected to meet when I first signed up for Seeking Arrangement; he was sweet, vulnerable, and real.

A Change of Heart

As the night wore on and the conversation grew deeper, I became more and more convinced that I couldn’t do this. Not to myself, and not to him. Even though I would have given him another chance at a second date, the fact that our first interaction was based on a possible monetary transaction felt extremely foreign and strange to me. I definitely understand the allure of the sugar dating arrangement — being with a distinguished gentleman who will always get the check and provide me with an allowance is way too good to be true. However, the truth was that being a romantic at heart made it extremely difficult for me to go out with someone for a quick buck. 

“Hey Timothy, I can’t do this actually,” I told him at the end of the night. “I can’t date you for your money. I’ve never done this before and I thought I could do this because I couldn’t find a job and my savings were depleting. But you are a genuinely good man and I don’t want to accept your money to hang out with you.” 

“What do you mean?” he asked. “You don’t have to think of me as your sugar daddy. Just think of me as your boyfriend, just treat me like your boyfriend. That’s all I really want and really need from you.” 

I died a little inside. I had grown to really, really like Timothy. I wasn’t sexually or romantically attracted to him, but he had a very attractive personality. I admitted that I have never ever tried a sugar relationship before and that I couldn’t put it past myself to do so, especially since I’d realized how much I’d connected with him at the end of the night. 

“I guess it’s a good thing that we aren’t going through with this, then,” Timothy told me. “I really enjoyed my time with you. Let me send you back to your place, at the very least.” I obliged, feeling relieved and glad that he remained a gentleman throughout the entire date. After Timothy sent me home, I gave him a kiss on the cheek to bid him goodbye and wished him all the best on his quest for love. Even though it was not the full Seeking Arrangement experience, the encounter was ultimately very eye-opening. Failing to go through with sugar dating elucidated my notions of self-concept, allowing me to recognize that I was a romantic who could not bring myself to adopt a transactional mindset toward dating. And so, later that night, I logged onto the Seeking Arrangement site to delete my profile.

Feature image by Sherryl Cheong

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