Secrets from a Dating Coach 

As a dating coach in Singapore, I’ve coached countless Singaporeans in their dating lives. What many don’t realise is that it’s not about putting on a facade, regurgitating pick-up lines or executing tricks and gimmicks. Instead, it’s about growing to become the greater version of yourself—becoming more attractive is simply a product of that outcome.

1. Let go of limiting beliefs

Common limiting beliefs in dating are that one has to be good-looking, rich or famous in order to be attractive. Let go of these preconceived notions as they do not benefit you in any way, and serve no purpose other than to constrain and inhibit you from putting yourself out there.

2. Focus on things you can control

Dating Coach_2


Being fixated on factors outside your control is pointless as nothing can be done to address them. Focus on things within your circle of control and act on them instead.

Outside your control: Not winning the genetic lottery, being below-average looking

Within your control: Taking care of your appearance by grooming and dressing well

3. Follow the 3-second rule

Take action within 3 seconds whenever you find yourself hesitating to talk an attractive stranger or ask a crush out on a date mid-conversation. Trying yields infinitely more chances of success than inaction. If you don’t even make an attempt, you are not allowing possibilities into your life.

4. Don’t take it personally

Deep down, you know who you are and what you have to offer. Being rejected is NOT a reflection of your self-worth. Use rejection to identify aspects for growth and learn to silence the negative voice within that hurts far more than any rejection ever could.

5. Kill your fears

Be it the innate fear of rejection, failure and judgment that everyone shares, or physical manifestations such as public speaking and heights, killing your fears always leads to confidence, which in turn allows you to conquer even more fears. It’s a cycle of never-ending positive feedback loops.

A good place to start is to..

6. Seek discomfort

“Do one thing every day that scares you.” — Eleanor Roosevelt

Being comfortable isn’t a place we learn or grow. Challenging ourselves to get out of our comfort zone is how we grow and allow amazing things to happen. Start by taking small consistent steps towards discomfort and before you know it, you’ll have progressed so far, your comfort zone will be a distant memory.

Start from something as simple as cold shower therapy—the act of taking cold showers as soon as you wake up. Not simply cold. Ice cold. Strengthen your willpower by seeking respite in the discomfort of a freezing shower instead of a warm and comfortable bath.

Whenever I stare at the shower head and entertain the thought of warm water flowing out, I tell myself, “If you can’t even will yourself to do something uncomfortable in the shower for 5 minutes, how are you ever going to accomplish anything that requires being uncomfortable in life?”

7. Names are important

dating coach singaporeSource
Dale Carnegie’s famous quote rings true today as much as it did decades ago  

Put in the extra effort to remember the names of people you meet and call them by name in the conversations you share. It helps to make them feel important and valued. This simple thing allows them to feel more comfortable around you and fosters the development of a connection.

Also read: 

Gay Guys Advise Straight Guys On How To Ask Girls Out

8. Give and accept genuine compliments

Generic compliments commonly uttered during dates are meaningless and often serve to do more harm than good.

“You have beautiful eyes.”

“You have an amazing smile.”

These ‘cut and paste’ compliments can apply to practically anyone. They come across as shallow and insincere, making your date wonder about your hidden agenda.

Focus on what you specifically appreciate about your date that is unique and central to their identity. If they are really friendly and outgoing, you can compliment them by saying:

“You’re such a positive and upbeat person!”

This makes them feel special as it acknowledges their personality. They’ll appreciate a genuine compliment that relates to their perception of themselves much more than canned lines.

9. Master the art of deep diving

dating coach singapore

Conversations that are perpetually stuck in small talk mode don’t allow you to get to know anyone any better. Deep diving goes beyond the surface by steering the conversation in the direction of finding out what makes the other person tick: their feelings, dreams, motivations, beliefs and convictions.

Instead of harping on boring topics, initiate the deep dive with these conversation starters: If you had all the money in the world, what would you do? What is a quote that you live by because of its meaning to you? If you could wake up tomorrow, go anywhere, do anything, what would you do?

All these topics are open-ended, steering the conversation to the direction of possibilities. It helps the other person tap into their emotions and feelings instead of logic. Another tip: avoid logical conversations on topics such as work and school for too long.

Lead the interaction towards the direction of building rapport and a connection by diving deep. Treading around the surface is a sure-fire way to ensure both of you end up nowhere closer at the end of the date than before.

10. Stick to Pareto’s Principle

This is also known as the 80/20 rule. A common mistake I come across is when a man continuously talks about himself in the hope of impressing his date with his accomplishments, not realising he is not giving her any opportunity to talk about herself. The worst part is being oblivious to it!

80% of the interaction should be finding out about the person across you while talking about yourself should be kept to 20%. The best way to do this is to…

11. Prompt them to share about themselves

Want to know an open secret? Everybody loves to talk about themselves. Being skilled at prompting others to share about themselves because you are genuinely interested makes the conversation flow much more easily as the topic is something that they know better than anyone else. This puts the pressure off them and allows them to experience positive feelings that someone is genuinely interested in finding out what they are truly all about.

12. Be an active listener and relate

Not knowing what to say and entering ‘interview mode’, where your date is bombarded with question after question, is not a good experience for either party. You will impress them much more by being present in the moment and actively listening, steering the interaction to your desired destination and relating to them by empathising with their feelings and emotions.

Tips on active listening are:

Be present and stay in the moment: pay attention to what they are saying in the now instead of having your mind wander off or think about what to say next. 

Don’t be afraid to interrupt to clarify certain points of what they are sharing. It will draw out further responses and encourage them to expand on their ideas and provoke thoughtful responses.

Summarise and mirror the information and emotions they share back to them. Emphasising the key notes of what they have shared and relaying them back helps them understand that you relate and care about what they are saying.

The secret to being a great conversationalist is not in being a great speaker, but an amazing listener.

13. Develop empathy

Empathy is a soft skill that takes time to develop and requires having a genuine interest in other people. It means having the ability to accurately sense another person’s point of view and experience their internal world. It gives you the capacity to discern and respond appropriately to the moods, motivations and desires of those you meet and will dramatically increase your success in dating.

An actionable way to actively develop empathy with deliberate practice is to constantly put yourself in the shoes of others, even those you disagree with. Challenge yourself to empathise with people whose beliefs you don’t share and imagine living their life through their unique experience. Seeking to understand and respect opposing points of views is one of the best ways to develop emotional intelligence and empathy.

14. Don’t be needy

Someone whom another person can respect and feel a strong attraction towards will never be someone inordinately needy. Neediness is a form of insecurity, jealousy and approval seeking—an instant attraction killer.

Needy behaviour: confronting and demanding an explanation from the person you fancy as to why they suddenly stopped replying to your messages with an angry barrage of texts.

Non-needy behaviour: Being unreactive to their change of heart, and dropping a casual text to ‘ping’ them a few days later. If it goes well and they reply again, great. If not, move on.

15. Destroy the ego

Validation should come from within, not from external sources. Relying on external validation to feel good about yourself is to be a slave to what others think of you.

DEER — Defend, Excuse, Explain, Rationalise — is what our ego does when attacked.

Starve and eventually destroy the ego. Instead of taking rejection or failure as a personal affront, understand that they could have been having a bad day, their dog may have just passed away, they’re simply not interested in dating or a myriad other reasons. Detach outcomes from the ego instead of taking it personally, and learn to move on.

16. Have non-zero days

A zero day is one in which you have done absolutely nothing to get closer towards your goals or dreams. One of the best ways to evoke real lasting change is to strive for non-zero days. The aim is not to achieve tremendous success as quick as possible, but to consistently have a non-zero day, every day.

Do one push-up. Write one sentence. Read one page. A tiny bit of progress is better than no progress at all. Stalling progress with a zero day makes it easier to remain at rest and get stuck in a rut rather than pushing onwards. Likewise, being in constant motion and moving forward every day, no matter how small, will ensure the momentum keeps you going.

17. Take massive, determined action

If there is anything you want in life, you have to go out into the world and work for it; sitting back passively will never yield any results. Expose yourself to more social interactions in a non-friendship frame, for instance by approaching an attractive stranger and conveying your interest with intent. The emotional wisdom garnered through these reference experiences will be invaluable.

Stop staring at that cute barista at Starbucks and go say hello! Ask your crush whom you’ve been texting out on a date! Don’t be attached to one outcome; instead, be accepting of all outcomes.

*This is a submission piece by Executive Coach Malcolm from Social Skydiving Academy. Together with his team, he has helped many Singaporeans improve their romantic lives through honesty and authenticity.
This article was first published on 21 March 2019 and last updated on 5 December 2023. 

Also read: 

10 Times Singaporean Millennials Made The First Move And How It Led To Love