Game, Set and Match – the art and science of matchmaking

Sep 16, 2020

In a social media world, where you can swipe right to make a match, finding the right person to marry requires a much more old-fashioned approach says this professional matchmaker.

Anisa Hassan, Founder, Date High Flyers

SINGAPORE:After spending between eight and 10 hours at work as a professional matchmaker, the last thing I want to do when I get home is to binge watch on reality TV shows relating to dating or matchmaking.

I hardly find myself glued in front of the television except for the usual reruns of “Big Bang Theory” and “Friends” that are always in the background while our family is having dinner.

But during the circuit breaker and having to work from home, I found myself having more time to wade into these very shows I avoided.

It started with the dating show “Love is blind” where a group of single 20 and 30 somethings experimented with the premise that they can convince themselves to fall in love with strangers they cannot see while lounging in individual “pods” separated by a thin wall.

And within a week, several of these couples got engaged – they only meet face to face for the first time, after the first proposal. The show then hurried them into a co-habitation period and into a quick wedding, all within a month.

Out of the six couples, two got married and it left me to wonder whether they really knew the qualities they wanted in a partner or did they just get lucky?

Before long, Indian Matchmaking made its debut and took social media by storm. Culturally, I am conscious that the approach employed by the matchmaker Sima Taparia is quite different from my own.

But I found some similarities – she’s genuinely concerned about making a good match, while making sure that she meets her clients’ endless list of demands.


The honest truth is, people do make decisions based on who they are attracted to but there’s no reason to walk on eggshells around that. My clients, who are accomplished professionals, come to me looking for beauty, security and power at the outset, partly driven by this digital, social media age, which makes it easy to peep into the lives of “power couples” who seem to have it together.

After all, who doesn’t want the bragging rights of having a partner with looks, money, status? It is similar to other achievements on a resume. Men do look for women who are younger, more beautiful, those who are young enough to bear children.

While women focus on men with deep pockets. Sadly though, several of my clients have let many a good match get away because they held on quite tightly to this paradigm of what a good partner means.

I distinctly remember a client whose high end, fashion sense seemed to jump straight out of a Vogue pictorial when she walked into my office in 2005. Fiona (not her real name) was a 28 year old banker and had wanted to be matched with gentlemen who were strictly living in districts 9,10 and 11. I told her that I was a matchmaker and did not work for the postal service. Fast forward 15 years, the same individual reappeared in my office, this time having gone through a bitter divorce.

After years of interpreting and analyzing data from close to 12,000 singles and examining potential compatibilities and complementarities of personality traits, I’ve come to the conclusion that those who have been divorced tend to be clearer about their choice for a partner. They also have a better understanding of what’s truly important in a marriage. The trend of remarriage in Singapore is also on the rise with four in 10 of my clients having said “I do” in the past.

While a 2019 Pew Research Centre findings stated that seven-in-ten adults (71%) claimed it was critical for a man to be able to support a family financially to be a good husband, many of my upscale clients were indifferent towards that. Rather, the top three qualities that they look for are better communication, being trustworthy and having kindness.

Clearly for Fiona, her paradigm shifted after her marriage to a venture capitalist collapsed within two years. Armed with the knowledge that she now has, she wanted me to show her the ropes and we created a framework where her top priorities included fidelity, similar faith and someone who could make her laugh.

If my own marriage of 22 years has been instructive, I would say our journey was less Jerry McGuire (You complete me”) and more Big Bang Theory, Sheldon and Amy’s “you complement me”. Despite our different pursuits (my husband has a Ph.D in Finance whereas I’m just Dr. Love), he complemented my strength by being my numbers guy while I remain front and centre with all the clients in our business.

Over the years, he has brought balance, structure and purpose to my once chaotic life.

Growing up with nine other siblings, I instantly recognized and appreciated that he had a better structure, system and vision which I was drawn to. Did I have that realization at 17 when I first met him?

Well, not at all. But I know that awareness became more apparent over the years and when I finally walked down the aisle nine years later. We both knew over the years that marriage was above all else, all about team work. In each other, we found good team mates who could take on life’s many “projects” and hopefully like Sheldon and Amy, take home the “Nobel Prize” some day.


In any successful relationship, there’s no one size fits all. One has to take into consideration the journey you’ve been through and look for opportunities to be with someone who makes you feel safe, supported and appreciated.

After pairing more than 1000 couples, I believe the biggest barriers to our heart stems from our biases that’s entrenched in the framework of looks, money and power. We spend so much time focusing on these attributes when searching for a partner that when we finally have him/her, we wonder why is something still missing?

So, what makes a relationship enduring and better able to withstand the vicissitudes of life? I would put it down to these key things:

You values are aligned: Whether your values are based on faith, being family oriented, having growth mindset or travelling the world on a shoestring, it certainly helps when your partner has a lot in common with you. Despite the old notion that opposites attract, a compatible partner naturally gravitates towards people who are familiar. Couples with similar values have the propensity to turn towards each other instead of away. They think, feel and act in synchrony and since most acts of turning towards are small, everyday gestures of appreciation, understanding and kindness, it makes living together easier and more manageable. Couples with similar values iron out difficult conversations earlier in their relationships. They don’t shy away from discussing the division of household chores and finances, having children or living arrangements with aged in laws which can implode very quickly if left unaddressed.

Being agreeable and having an emotional connection: In a six year follow up study of newlywed couples at the Gottman Institute, those who remained married turned towards their partner’s bid for emotional connection 86% of the time, while those who divorced averaged 33%. When the emotional bank account is in the red, partners tend to question each other’s intentions, are quarrelsome or even lonely. And when the account is in the green, partners tend to give each other the benefit of the doubt during conflicts and are generally more agreeable in nature. To be satisfied in a relationship, couples must focus on increasing deposits (of positive interactions) and minimizing withdrawals (of negative interactions). Having a partner who sees the big picture and are generally agreeable, helps restore harmony in a conflict where the focus can swiftly change from “who’s right” to getting it right. Having someone who’s easy to get along with and is agreeable have been underrated virtues that I now advocate for my clients.

Being dependable and trustworthy: You know your relationship is here for the long haul when you can’t wait to get home to share your day with your partner. He/she makes you feel completely safe about being vulnerable because sometimes even the strongest people need a shoulder to cry on. On top of that, you have full trust that even when you make mistakes, lose your job, fall from grace or just need to pause and start all over again, your partner will be ready to pick you up, walk the journey and have your back under all circumstances.

The decision to get married is one of the most important decisions that one has to make in this lifetime. So why leave it to chance or be in a hurry to make one? You don’t have to do it twice to get the lesson right.

In the case of Fiona, it no longer mattered that her new partner isn’t from the financial industry. In fact, never have she imagined being with someone from a different ethnic background, let alone an engineer. But not only did her new love bring her lots of laughter, he made her happier and helped her find her peace.