This is a new series that I am starting – Dating Advice for Guys (DAfG).


Often in your dating journey, you will encounter someone whom you are deeply impressed with. Your friends will ask you to stop dreaming as they think that she is out of your league. Well, truth is, there is no harm trying right?

So first and foremost, the F word. How do you conquer the fear of disapproval and rejected?

Fear of rejection is detrimental to your dating life as it will make you freeze and stop you from functioning properly. You might be so uptight that you might start stuttering, your words coming out all wrong etc. Chances are you fear rejection because you have been rejected so many times and you are afraid that it is going to happen again. The thing is you are probably lacking in confidence. So if you build up your confidence using the steps stated below, you probably would have a foot in.

Step by step guide to boost your self confidence:

(a)    Change your mindset: Often, it’s all in the mind. You have to change the messages that you are telling yourself over and over again. Instead of saying thing such as, “I am such a loser, no girls will like me,” or “I am not successful enough, I am not funny enough,” try changing these lines to positive affirmations of yourself. Be positive. “I am sociable.” “I am confident.”“People will accept me.” “Girls will find me attractive.” Once you start to believe them, the way you carry yourself would be different.

(b)   Step by step: Do not jump into the deep end. If you are shy approaching women whom you are interested in, or your long-time crush, start taking baby steps by talking to women whom you meet on a daily basis e.g. the cashier at the supermarket. Just by saying hi and asking them how they are doing, will eventually help you build up confidence on approaching ladies.

(c)    Keep at it: Along the way, you might feel uncomfortable with all the changes that you are making to your life, or you might not see any improvement despite having make changes. Like anything else in life, it takes time. So set a medium to long term goal, and keep at it. Do not give up like after a week.

The secret is really to just get a conversation going. And once you do that, things will just fall into place. Even if she does not happen to immediately agree to go out on a date with you, you have made a new friend, and who knows where that would lead to. If you have been using rehearsed pick-up lines, maybe it is time to stop and be more genuine and more natural.

Now that you have boosted your self-confidence, here is your game plan for snagging a girl who is ‘out of your league’:

(a)    First and foremost, realise that beautiful, smart, rich women are people as well. They are not goddesses, even though you might see them as such. Hence, stop being intimidated. If you cannot get over this fact, you are unlikely to succeed.

(b)   Next, do your research. You might be surprised but the more beautiful or attractive or rich or smart a woman is, chances are she can be quite insecure. She is constantly worried that guys are only after their looks, or their money etc. Hence, the question is, how do you make her feel self-assured? Be a good listener, be a good conversationalist.

(c)    Women who are “out of your league” generally would have many suitors. Hence, they have had many experiences listening to bad pick-up lines, or men trying to flatter them, or men trying to worship the ground they walk on. Hence, do not ‘suck up’ to them. The more you do it, the less value you have in their eyes.

(d)   Know your strengths and play them up. Create situations or scenarios where you can show off your unique qualities and impress her. E.g. if you are a talented singer, or if you can cook really well. When you are doing something you are comfortable in your own skin, you will appear confident and attractive.

(e)   Last but not least, re-examine your objective of approaching women who are out of your league. Is it because you are looking for a trophy girlfriend or wife? Is this girl truly compatible with you? Do you like her for the right reasons? Because sometimes, there are girls whom you might not be attracted to initially, but you guys are actually a match made in heaven.

Happy dating!

(First appeared in New Man Magazine August 2009)