To Break My Streak of Failed Romances, I Rented a Date for a Day
All images: Liang Jin Tey/Rice Media

Every family gathering, my wise aunts would collectively toss me a deep, philosophical question. One that begs rumination: “Ah boy ah, got girlfriend already or not?” 

My standard answer: “No girlfriend leh.” 

They then swiftly proceed with a string of follow-up questions that casually sends one further down the existential spiral. 

“Why don’t have?! You so handsome?!” 

To which I reply in resignation, “Oh, I am single by choice. Just not my choice.” 

Throughout these 24 years of my life, the only long term relationship I had was with my, ahem, right hand. I never had stories of hanging out with a secondary school sweetheart, nor have I been tagged in Instagram posts by anyone saying they’re proud of me for completing two years of compulsory conscription. 

Most of my love stories revolve around meeting a girl on a dating app, thinking that she seems really nice, meeting her, and then getting ghosted. This may or may not have negatively affected my confidence and self-esteem (spoiler: it has). For someone who’s had issues with his mental health and struggles with perfectionism, these seemingly small failures have crept up on me from time to time.

Dating is hard, especially now in the 21st century. Despite us being more connected than ever, it feels harder to form authentic relationships with new people, and this is especially true in times of the pandemic. Even online dating posts numerous challenges. The match disparity between men and women is huge, with women statistically getting more matches than men, despite swiping way less.

For men, the challenge is to stand out immediately in your profile. For ladies, it might come in the form of horrible pick-up lines bordering on sexual harassment.

So one day—probably after a few drinks—I decided to stop feeling sorry for myself and hopped onto one of those Rent-a-Date apps that I had been hearing so much about. I badly needed a review about how to improve my dating skills and what better way to do so than fork out some good ol’ cash as an exchange?

Finding the service was the easy part. I did a simple Google search and a couple of companies popped up. I went with Maybe, just because they had more “partners” to choose from.

But choosing a specific date was harder for that exact reason: there were too many girls to choose from. I chose a bunch from those within my budget of S$150 and sent them to my close friends. I would go with the one with the most votes, thereby taking one step forward towards my ingenious plan of an eventual classic BTO happy ending.

Day of the date

The next problem came up on the day of the date. I wanted to dress comfortably, but still look fabulous. Thankfully I had the help of my younger sister, who helped me pick out a Japanese-inspired outfit that consisted of what looks like a black bathrobe and a plain t-shirt. A couple of OOTDs later and it was time to make my way to the pre-arranged cafe for a nice cup of afternoon tea (or coffee, if she so prefers).

Seeing how my dating skills were essentially being reviewed (as per my personal request to the girl), I decided to buy her a stalk of flower to leave a good impression. Inside the flower shop, I felt incredibly out of place. I’ve almost never bought flowers for anyone before, and I did not know what to look for beyond the price tags and the knowledge that roses=romantic. It was also here that I made my first major realization: flowers are freaking expensive! $16 for a single stalk?! I could buy a good bowl of Mala Xiang Guo or a pint or two. So… I’m literally paying to be romantic. Cursing the big bad flower conglomerates, I bought a stalk of the blue rose.

Throwing in some chocolates for good measure

After the 2 gift stops, I finally reached the date location, Haji Lane. Walking up to the cafe where I had planned a quaint cake and coffee-tasting session, I realized I had colossally screwed up. *cue cinematic sound effect* 

The cafe was, unfortunately, closed for the day. This sent me into a state of intense panic. Feeling like the biggest fool, I scuttled around and eventually settled for a small, Hawaiian-themed hole-in-the-wall cafe that was clearly in an early Christmas mood.

Lo and behold, my date for the day, Jolline. 

Jolline, my date for the day, arrives, and we greet each other. Immediately it seems like I’m the more nervous one between the both of us. We both looked at the menu. She chose a latte with less coffee and I went with a non-alcoholic fruit punch against my desires and to not seem like an alcoholic. Jolline started telling me how she was trying to cut her coffee intake, and the ice slowly breaks as our conversation takes off.

We seemed to hit it off well, and in my view, it seemed like she was responsive and not just “blue tick”-ing me in real life. Good sign. As we conversed, I learned more about her. Jolline’s a host and a streamer who had only been on the app for a month. Despite that, she is already seeing repeat clients. 

I ask her if loneliness is one of the factors that drive people to rent social partners like herself, and she says it’s a possibility but spins it in a positive light—loneliness could come with a desire to improve one’s quality of life.

“If none of your friends like to eat Western food, but you do, then you can find someone that likes to go with you,” she says. “And for more introverted people, it’s a way to practice their social skills, so that they can interact better with new people. It’s a start for people who want to go beyond their comfort zone towards forming new and more meaningful relationships.”

Jolline also added that renting social partners can provide a more neutral point-of-view on how to better improve on social skills. Friends may not be able to give you the most objective advice. Their advice would usually come in the lines of “just keep being you”, which may not always be helpful. Instead of running into the wall multiple times, why not try a newer approach and get someone who can be more objective?

We also talked about why maintaining a relationship in this generation seems much harder than before. Compared to our parents, who always seem to have their shit together, settling down in a HDB by 25 and having kids, we’re marrying later, still broke, and only have houses built in virtual worlds. Why was this so?

Done with my second drink

Over the next few drinks (more mine than hers), we talked about how our generation has become more self-aware of our wants and needs, and what we come to expect more out of a relationship. If someone isn’t “good enough” for us, we move on. But our wants may compound to a point of being unrealistic, and it’s important for us to adapt and keep our expectations in check in order to find more fulfilling relationships. 

At the end of the day, she made me realize that I should not feel so negatively about being single. It was a good reminder not to look at rejections as a form of failure, but understand it as a process of self-improvement—to become a better person for when the right person comes along.

The time we spent together went by easily, and at the end of our date, we took a picture and said our goodbyes.

Thank you random stranger for the photo!

The verdict

A few days passed and my written review by Jolline came in via text. It read like this:

First impression:

  • Seems like a pretty quiet guy, but turns out to be quite outspoken
  • First choice of location was closed, hence msg came in to change location (the research wasn’t done well)
  • Came with gifts, means actually quite well prepared and effort was put in


  • Easy going
  • Outspoken
  • Nice guy

Future notes:

  • Perhaps can think of better locations/activities

Armed with this knowledge and the experience of a not unsuccessful first date, I can now take a better look at myself. Through this review,  I realized that everyone develops relationships differently. I was always someone for whom first impressions were not important, but this has taught me that the little things like planning your day already make a difference in standing out. It helped me get past the dreaded first date barrier.

Some may criticize services like this as being a cash grab, or an opportunity for attractive girls to take advantage of single men. Do I feel like it is a transactional relationship? Yes. But, I also feel that it was money really well spent. Some people, like me, may need opportunities like these to bolster their social skills and gain some confidence and exposure.

Look at it this way, no sane person you meet on Tinder will tell you what you need to work on after going out on one date with you.

If improving yourself and having pure, genuine fun with people comes at a cost, I don’t see why not. We already pay for dance classes and gym memberships, so to me, this is just a class for social skills.

In my experience, my date was focused on providing the best social experience for us.

It allowed me to come to terms with being single for the time being, and I’m happy to report that I’ve since broken my streak of getting ghosted: I’m currently meeting someone for the 3rd time, a huge personal record, and we are even meeting more in the future. I feel more at ease in one-on-one conversations now, and feel more empowered to be myself.

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