A Letter To Clarissa

As you can see from my reaction in the picture, I am not too sure how to handle the affection of a three-year-old woman when she wanted to kiss me.

After Mummy Jenny saw the picture, she mentioned that she have not yet taught her daughter on how to handle guys since girls should not take the initiative so quickly. This is because guys like girls who are challenging.

I advised Mummy Jenny better not teach her daughter to be challenging because the women in my office are also challenging and most of them are still single.

Anyway since I feel guilty about avoiding Clarissa that day, I shall give Clarissa 3 tips on how to be a challenging woman.

Based on my 29 years of experience talking to women (and still not good at handling them), here are the 3 easiest ways to be challenging.

1. Give ambiguous answers
The more ambiguous the answer the better.

Use it to confuse men, make them read your mind and guess what you want. This will ensure that he will be thinking of you the whole day and trying to figure you out.

An example of an ambiguous answer is when he asks you a question, you reply with “what do you think?”

When a man’s face looks blank or he says “huh”, it means you have succeeded.

2. Never say yes
You can say any answer like “can”, “ok” or give a long indirect answer but just don’t say “yes”.

The theory is that it makes you look easy and not challenging if you say the word “yes”. (I think so, in fact I am not too sure about this theory)

The preferred choice is actually to give a long indirect answer. And the most useful way to do it is to first say “no” then say “yes” indirectly.

An example is a man asks you for lunch, first say “Don’t want”, then after a 3 second pause, say “anyway no one is stopping you from having lunch with me.”

Again when a man’s face looks blank or he says “huh”, it means you have succeeded.

3. Always pretend to be busy
This has something to do with the economic theory of demand and supply.

It is like your time is so scarce (rare supply/availability like diamond), that demand (theoretically) will be high because it is not easily available (read challenging).

An example is when a man asks you out, tell him that you are busy with ______ (fill in the blank) on that day and will not be able to confirm with him until ______ (fill in the blank). Make it like really last minute when you agree. Also when you finally meet him, meet for only 1 hour.

Alternatively agree to meet him then cancel the date 3 hours before saying you have something else. According to a woman friend, this is ethical because 3 hours is enough time for him to arrange another activity. If he is interested, he will (stupidly) forgive you and ask you a second time (to get tortured).


After giving you these 3 pointers, I hope these tips will help you to become the most challenging woman in Singapore.

So Clarissa, when you are 19 and realise many men are dying at your hands, remember to thank me and no you don’t owe me a kiss even if you miss it that day.

And also remember that I am the most challenging man in Singapore because you didn't get to kiss me.

Now that I feel guilty about betraying the male race, in my next post, I will teach men how to handle challenging women...