Dating: Former professional matchmaker on why she thinks people remain single

Geraleine Yap (left), a former matchmaker who worked at a local matchmaking agency in Singapore, shares her thoughts. (Photos: Geraleine Yap, Getty Images)
Geraleine Yap (left), a former matchmaker who worked at a local matchmaking agency in Singapore, shares her thoughts. (Photos: Geraleine Yap, Getty Images)

Matchmaking has always amazed me.

Unlike dating apps, where you create your profile, determine what to write in your bio, and chat to different people, matchmaking seems a bit more tedious, with structured processes in place.

However, unlike dating apps, a matchmaker does the work for you—for the most part, at least.

Recently, I spoke to Geraleine Yap, a former matchmaker who worked at a local matchmaking agency in Singapore to learn more about the matchmaking process, and some of the reasons why she thinks people are still single.

How long were you a matchmaker for?

I was a matchmaker for three years, during which in the final two years, I moved on to focus on high networth clients, and to also provide dating advice.

How did you get started in the matchmaking industry?

By chance!

I was taking some down time from my previous job, and saw a role being advertised.

At first, I didn’t take it too seriously and applied for it out of curiosity. I didn't think I would actually get it.

I went for the interviews and luckily I got through, and eventually went on to become certified as well.

How does the matchmaking process work?

It’s pretty straightforward.

Every client comes through a vetting process in which we determine whether they would be suitable, and if there were potential matches for them.

We get to know each and every client in detail. For example, we get to know their lifestyles, hobbies and religious background. We also ask them about their preferences.

From there, we handpick each match to ensure that the determined match works two-ways, meaning to say they both fit into each other’s preferences.

How do you determine that people are right for each other?

Chemistry is something that cannot be predicted or guaranteed.

If I could guarantee chemistry, I would be a billionaire profiting off the love industry.

However, in my experience, I find that the individual’s personality, similar values, and character can sort of be a indication of whether they would be compatible.

Usually, I feel this can be sensed better through face-to-face interaction with the client, so I know how they speak, their body language, the way they carry themselves and other subtle traits.

There are times when a person may be slightly out of the other’s preference (for example if she is two years older than his preferred age), and if I do find that it is a suitable match based on whatever reasons — perhaps they both shared that their favourite country is Japan for its culture and scenery which mean that they appreciate the same things — I may try to convince the other party by stating my reasons, and hope that they give each other a chance.

What happens if the matchmaking process doesn’t work out?

Most of the time, magic doesn’t happen on one date.

Yes, there are some exceptions that some couples hit it off right on their first match, but that’s not the rule.

Dating is a numbers game, the more people you date, the higher your chances. I think it’s also a good way to reflect and ask yourself why the date didn’t go so well, and perhaps find ways to improve your dating game too.

I also encourage people to refine their preferences or expand on it, so that it widens the dating pool and potential matches available.

What are some mistakes you tend to see from singles looking for a partner in the process?

Unrealistic expectations.

Most people think that because they are paying for a service, they demand more, and their expectations of their partner goes up.

Having a set of criteria is great and it shows that you think about what your future partner should be like, but at the same time, you can’t find someone who crosses 10 out of 10 points off your checklist.

At the end of the day, no one is perfect.

Are there any memorable couples you could tell us about?

The most memorable couple I remember was a couple who got together at the height of the pandemic.

Their first date was via Zoom, and they hit it off like a house on fire, and the date went on for five hours or so.

Eventually, when restrictions were relaxed, they met up. Long story short, they’re engaged now (maybe even married) and I felt that was something beautiful that emerged from the dreadful pandemic.

The worst date was probably a big reason why I feel ladies should always stay safe during the date, and not be afraid to call for help.

This match had their first date together in a bar, and the gentleman got awfully drunk.

He started to get rude and disrespectful when she wanted to leave, she was so terrified she had to hide in a bathroom stall and get a server to escort her out.

I blacklisted and banned the guy immediately after she told me about him.

What are some green flags people tend to overlook?

When the gentleman offers to pay for the first date.

So many times I see ladies taking this for granted, and thinking it’s the guy’s duty to pay and that him paying is a given.

It’s not. If he pays, it’s something the lady should always be appreciative of, no matter how small the meal is.

What are some red flags people tend to overlook?

If your date doesn’t say ‘thank you’ to service staff.

I find that being polite and respectful is the bare minimum. If they take the service for granted just because they're paying for the service charge, guess what else they’re going to take for granted in the future?

Has working as a matchmaker changed the way you approach dating?


I have learnt to be more communicative and honest with my dates in terms of what I am looking for. I don’t see a point in wasting the other party’s time.

Also, I tend to be more open minded when dating and also to give second chances.

Was it difficult for you to date as a matchmaker?

Yes… The number of times people have swiped left on me.

I once had a guy that, while we were just at the chatting stage on an app, didn’t want to meet me as he thought I was on the platform for business.

I am human and I need love, too!

What sort of advice do you generally give your friends about relationships?

I think it depends.

Sometimes they may come and ask like, oh this person said this or did that, what do you think they mean?

Some of them may ask me what they should do on a date, what they should wear, where to go and eat and stuff, and it’s all OK! I love hearing my friends out and giving advice!

Now that you’re in a relationship, what are some things you’ve applied from your journey as a matchmaker?

That communication is extremely important.

At the end of the day, a relationship is between two parties, and it’s vital to have a partner that you can express your thoughts and feelings to in a safe manner.

Healthy communication also helps the couple to resolve differences better, and to understand the opposite party.

What would you say is the main reason people remain single?


I know I have said this before, but it’s really true.

I find most of the clients who have found success have realistic expectations. Not to say that we should lower the bar and accept the bare minimum, but also to be realistic of what we’re looking for.

I think people really need to know that yes, you are choosing people, but at the end of the day, people are choosing you too.

A Millennial's Dating Diary series explores real-life interactions and the hurdles of dating in Southeast Asia. The series features the dating stories and misadventures of Arika – a 26-year-old, straight female marketing manager with a penchant for over drinking — and fellow millennials.