June 25

What dating advice would you give your younger self?


I sat in the taxi hearing my friend share about what he was doing with his date.

Calls. Long messages. Discussions over where their future will lie.

Deep down, I thought,


This was a lot of effort. And I just wasn’t sure I was ready to give that.

A caveat before we begin

Perhaps you might think that you’re reading the advice of a guru who’s got it all. Hundreds of dates in the bag, a beautiful wife, and a great family.

No, no and no.

All you’re reading is the honest reflection of a 27 year old who’s spent the last year treading gingerly into the world of online dating for 2 weeks, before stepping quickly out.

And someone who’s (some say ‘desperate’, I say) invested $540 to 12 dates with Kopi Date, a blind dating agency.

If I look back at the past year of this journey, 5 things I think might be helpful for you as you go on your own dating journey.

You will see this article framed in terms of the things you shouldn’t do, rather than the things you should. And here I think the wisdom is in terms of choosing not to make mistakes, rather than trying to do too many things.

Because if you search the internet for advice, you will easily find listicles of all the things you should do.

But the things you shouldn’t?

Well, that may be more important.

Don’t focus on the performance-based advice

When I was new to this, I had a friend who gave me lots of well meaning advice. He told me how he had paid $200 for dating advice from a guru, who then read his texts and told him how to reply.

Upon reading my messages, he gave me a few guidelines.

  1. Never double-text
    1. Meaning you don’t follow up a text with another one
  2. Take as long as the girl does to text
    1. If the girl takes 2 hours to text back, you take 2 hours too.
    2. If she does it in 3 days, you take 3 days.
    3. The point is to follow the pace of the lady, and not look too desperate.

In Mark Manson’s book ‘Models’, he shares about how this ‘performance’ method can sometimes work.

The first method (a man giving false impressions) occurs through what I call “performance.”

The vast majority of the dating advice out there for men (and women) is performance-based advice — say this, act like this, don’t call her back right away, pretend you don’t like her, make these jokes, etc.

Often we focus on performance driven dating, without realising that this shifts us towards seeing our own lack, rather than playing towards our own strengths.
Often we focus on performance driven dating, without realising that this shifts us towards seeing our own lack, rather than playing towards our own strengths.

To my friend’s credit, this advice did work for a while.

But slowly, I found myself not enjoying myself. It got too anxiety-provoking to wonder whether the lady was ignoring my messages.

If you’ve ever been in the place where you’ve worried about why the lady is not messaging you back, and you’re busy catastrophizing about the end of the world with your date, you may be following the performance-based model.

What may be more useful is to build an internal locus of security that’s not just based on what your date thinks about you.

If you look at the men you admire, you might notice some aspects of them that make them attractive.

They don’t appear to try too hard. They have quiet reservoirs of confidence that make you think that whatever the girl thinks of them, it doesn’t really matter.

As someone who hates text messaging, I’ve heard time and time again advice about how I need to check my phone more often, and to reply faster.

Sometimes I just think,

Ah screw it.

I will just do what I want.

It’s the same for you. You might have a particular idiosyncrasy that seems weird to others.

Maybe you like line dancing. Or you like watching independent movies. Or you prefer to spend time in the library over cafe-hopping.

Whatever it is, it is you. And that’s what matters.

Giving that up to attract the right lady might not be wise.

Don’t woman please

Here is the crux of the issue. As argued in the likes of ‘No More Mr Nice Guy’, we often find that as men, we ‘women-please’ to try and get what we want.

Dr Glover shares about how we grow up emasculated as a result of the influence of our mothers.
Dr Glover shares about how we grow up emasculated as a result of the influence of our mothers.

It’s a throwback to our growing up years, where we heard mummy tell us not to do this and that, and we ended up pandering to her interests, rather than yours.

This can be dangerous in the opening phases of knowing someone. In the first date I found at university, I kept trying to make her happy. I would give her whatever she wanted.

I would rarely make my own interests known. After all, it seemed smart.

If you gave the girl what she wanted, she would give you what you wanted in terms of love.

It didn’t work.

Looking back, what might work better is to make it a balance between your interests, and her interests.

It’s not just about saying ‘no’ to her every request. Rather, it’s about learning to state firmly what you want too.

We tend to be afraid that saying what we want might chase the lady away. We fear looking brash and abrasive.

But it is in sharing what we want, that allows to eventually get what we want.

Not being needy

Mark Manson does have some healthy principles in his book, Models.
Mark Manson does have some healthy principles in his book, Models.

Mark Manson calls this ‘non-neediness’, where

a man places a higher priority on his own perception of himself than the perceptions of others.

A non-needy man’s actions and words will therefore be primarily motivated by embodying his own values and desire​s.

It’s not just about being rude to the ladies around you, and looking badass, just so that you can look like you don’t ‘really care’ about women.

Rather, it’s about learning to have the right intentions, the focus on the things you can control, and the right investment in oneself, rather than others.

  Non needy, healthy male Needy male
Purchasing Behaviour Buys what he likes, and rarely finds the need to flaunt them Buys tickets to fancy meals, talks about the latest expensive gadget he has, so that he can impress others
How he interacts with friends or acquaintances True, authentic self Constantly trying to shape their perception that he is a ‘nice’ guy, when he doesn’t really want to be, or care about the problems people have around him
Intent Does things because he likes doing them and wants to Does things for approval

Learn to call it quits fast

I remember my last date. Let’s call her Pat.

Pat was well-read, smart, and diligent.

A little too diligent.

She was going for 4 dates a week. She was also regularly late.

I kept persisting because I thought I should learn to be understanding, and not try to be mean and rude by asking her why she was late.

6 dates later, things boiled over.

That Saturday morning, I told her that I was pissed that she was always late.

We stopped seeing each other after that.

Perhaps the biggest lesson I learnt from that was recognising that when problems appeared, learning to communicate them quickly was best.

At the end of the day, this story always strikes me.

It was the last session of the 27 sessions I had with my therapist over the year. She had seen me through some dark times, where I had complained about how depressed I felt about the failures in my studies.

But as she closed the session, she said something that surprised me.

I honestly believe that you’re a perfectly fine, and great person.

It’s whether you believe that too.

And for you reading this, it’s believing that you’ve something worth loving in yourself too.



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