Interview with Cindy Leong, Dating and Relationship Coach

Cindy Leong relationship coach

Cindy and I are from the same business networking group, and I dare say I’ve never met a coach quite like her. She’s a dating and relationship coach, life coach and business coach rolled into one and she dishes out advice which might seem unconventional at first, but then ends up making a lot of sense. For instance, she and her husband have no qualms sharing with each other and laughing about their past relationships, as they take each (failed) relationship as a point of reference for improvement, instead of the start of reminiscence. This runs contrary to what many relationship coaches say about past relationships being a “taboo topic”.

Cindy is also a huge fan of giraffes and has a Giraffe Room at home. Interestingly, the BTO flat she now resides in with her husband is the one which he had applied for together with his ex-girlfriend. Instead of feeling uncomfortable, Cindy is happy that she did not have to wait, like every other couple who applies for a BTO flat, for the keys. They did the name change in the application, and voila, she has skipped to the head of the queue. 🙂

Cindy and her first book:

Cindy Leong dating relationship coach

A cozy corner in the Giraffe Room:

Cindy Leong dating and relationship coach

Cindy says she likes the giraffe because it is “cheerful, chirpy, friendly”, and I’d say that somewhat describes her too. Having said that, know that she is a coach who will give you her no-holds-barred take on what you need to get done, and I get the impression she’ll give you the ass-kicking required to accomplish your goals too. *wink*

And here are my 5 questions for Cindy:

1) Is there really a Mr / Ms Right out there for everyone, or do we just learn to accept people as they are?

You have to first be the right one to attract the right one. Usually people go to a dating agency and state their demands. But if you are a level-2 chap and you want a level-10 girl, that’s impossible! Even if a level-10 girl is attracted to you, it’s likely for the wrong reasons.

What are these levels? They are from a socially agreed-upon kind of ‘scale’. In Psychology, we call this “Mate Value”. If you date someone with a lower mate value, you feel lousy about the relationship, and you don’t feel like bringing the person out with you.

It transcends beauty/looks as it’s also about the person’s character. (Check out this article:

For instance, if I believe my mate value is at least a 7, I won’t settle for a guy with a mate value of 1, who doesn’t work, has bad grooming, and is procrastinating all the time. Having said that, if you are a 10, and you happen to see the potential in a 7 or 8, then you might still take the chance. If a guy is generally a nice person, caring, and responsible, at about 5 or 6, but just does not have good grooming, you might still give it a go. When I first met my husband, he was just a 4 (to be very honest). Then when I got to know him better as a friend, his character is what attracts me, so that brings him to a 5 or 6. But the outward bit was still lacking. I suggested a revamp and he was open to the challenge. My point here is, it is important that he decides to make the change(s) out of his own will and motivation.

If a man is doing a revamp (or any change) just for you, he has just won himself the bullets to arm-twist you in the future. He may do it halfheartedly then when it backfires, he may blame you for how it doesn’t work. Most importantly, never go into a relationship or marriage expecting the other person to change.

2) What are the differences you’ve noticed between coaching men vs. coaching women?

Men are generally more defensive while women are more willing to spend and invest in their lives. I have to be brutally honest with the men, and give them the truth in an in-their-face manner. Most are not open to grooming sessions so I have to say something like “You tell me you are 32 years old. Can I be honest with you? You look like you are 38.” Yes, you have to just ‘give it to them’ in a straightforward manner. Only then will they wake up their ideas.

3) You conduct so many different workshops. Which is your favorite one?

The Enneagram workshop, because whatever the issue, we have to work on fixing what is internal first. For instance, a guy may be well-groomed and sweet to people but not “authentic” and doesn’t know what he wants so he still ends up in the wrong relationship. Many have to learn to be authentic.

And what is being authentic? I’ve met a lot of nice guys who are just nice but don’t portray the right image. They may be a 6 or 7 inside but portray a 2 on the outside. Others may just be 2s but portray themselves as 10s – that is simply lying and putting up a cover.

4) You’ve interviewed so many couples for your book ‘SuffeRing or ConqueRing – Happy Marriages in Singapore’. What’s the most important ingredient for a happy marriage, and do you also do marriage counselling?

It still boils down to communication and relationship management. Sometimes, problems are due to external factors such as a friend, job, boss, or mother-in-law. Communication and openness is key. For example, when the wife says “Your mom has been doing this…”, the husband should not ‘judge’ her or be offended (“Hey that’s my mom”). Instead, he can say something like “I’m sorry to know you are thinking this way. How can we solve this issue together?”

It’s important that no one’s views are discredited. Don’t demean or discredit your spouse as that usually leads to a marriage breaking down. Problems in marriages are usually caused by personality problems, and that’s where Enneagram can help.

I once helped a couple experiencing problems even after 10 years of marriage. The woman is a go-getter and the husband is the “chillax, ‎take it easy” kind. The wife often has a lot of expectations of the husband and he finds it hard to match up to her standards. She tends to get frustrated and the husband usually returns home late as a form of avoidance from possible conflicts. They were growing further and further apart. After 2 sessions of Enneagram coaching, they began to see the root of the problem. Both parties started to focus on each other’s strengths, and learnt about ways to affirm each other and work effectively as a team. The wife learnt not to impose her working styles on the husband but to use the lingo that motivates him. Their ‘near break-up’ marriage was restored.

Enneagram is about being versatile, operating in the other person’s ‘language’ and methods. And awareness of the various “types” is always the first step.

Sometimes people need help with their past baggages and require inner healing. They also have to clarify their life goals, learn how to be assertive about their view points, and fix their life before they go dating. I call this ‘Responsible Dating’. 🙂

5) You organize a very interesting dating event called ‘Dating In The Dark’ in which singles meet at a restaurant and dine in the dark. Any interesting stories to share?

Dating in the Dark

The feedback is usually very good. There are no shocks due to the prior screening which I do. I ensure their grooming is ok, and I handpick the people who attend. I will also meet those I don’t know first, and check if they can hold a conversation because it would be extremely awkward if they cannot talk during a date in the dark! Sometimes, I offer tips on what to wear to look presentable that day, so as to make that good impression last once the lights are switched on.

I’ll usually organize events at the more atas (high class) locations, such as the Fullerton Hotel. I do my best to push the envelope and come up with interesting events. Take my Improv Drama workshop, for example, it is one of my customer-centric events. It helps participants to be more artistic and engaging, qualities which Singaporeans tend to lack. Improv Drama offers an easy gateway to be creative and to be in touch with your emotions. Our society is not creative enough – there is definitely room for more creative expression and for people to better demonstrate their feelings.


Enneagram workshop

Thanks to Cindy’s recommendation, I’ve taken the Enneagram profiling test which comes with a total of 200 questions. In an upcoming post, I’ll share about the results and what I think of the coaching session with her. I do find her rates for 1-to-1 Coaching very affordable, especially if it helps you “Experience The Metamorphosis” (as in her company’s slogan). If you’re single and ready to mingle, here’s one site* you should check out:

Cindy Leong relationship coach

*There are recordings of the media interviews she has done previously. Listen to those and you may just pick up some very useful tips! 🙂