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Confessions of an International Playboy

Confessions of an International Playboy

Confessions of an International Playboy

Words by Wendy Tse

I’ve been close friends with Matt for many years, a man who, as much as I hate to admit, has perfected the art of seducing women. He is completely self-taught, using only trial and error, keen observation, and an accumulated understanding of the female psyche.

He started dating at 12, and since then, he’s gone on to date many, many amazing women. At our last count, he’s dated women from more than 25 cities. You’d probably imagine that Matt is tall, handsome and rich. In reality, he’s your average Joe. He’s Asian, 34, works in finance, and is of medium height and build. He’s not exceptionally good looking or sexy. He spends his time doing usual guy stuff.

The beauty of Matt’s approach is that he is NOT a pick-up artist. Matt sincerely puts in the time to get to know a girl, and his approach is never the same for any two women.

Being a matchmaker, I see a lot of great guys out there crash and burn during courtship. Some get rejected before the first date, some are unable to lock in a second or third. Many get friend-zoned along the way. Some have gone on more than 10 dates with a woman but are still going nowhere. And that’s when it struck me – if I were to break down his approach into a series of steps, I could essentially teach anyone to be infinitely more successful with women. So here it is, this simple yet powerful list.

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Appearance – Dress to impress

Matt is in good shape and goes to the gym regularly to keep fit. He maintains a healthy diet. He makes an effort to buy flattering clothes, nice shoes, and accessories. He gets good haircuts and stays well-groomed.

As much as men enjoy dating a woman who is beautiful, fit, and classy, women enjoy the same thing in a man. Up your game, and your success rates will follow.

Mind & Spirit – Learn to say “no”

On top of working on his outward appearance, Matt takes time to practice self-care. Practising self-care is taking deliberate, self-initiated steps to preserve the health of your mind, body and spirit. He knows exactly what he likes, and he purposefully sets time aside to enjoy these pleasures.

For instance, he always makes time to indulge in his hobbies and interests, and to get enough sleep. He takes care of his spirit by never hesitating to say “no” to anyone. He doesn’t factor females into this aspect of his life at all. Too many men spend all their time mulling over their career and women, and end up sacrificing self-care in the process.

Attitude – Don’t worry, be happy

Not many things in life can get Matt down. He doesn’t sweat the small stuff, and he once told me that he believes he is “generally a lucky person”. Unbeknownst to Matt, this told me a lot about him.

Richard Wiseman, a professor at University of Hertfordshire, conducted a 10-year study on the nature of luck, and concluded that a significant portion of one’s good fortune is not random, but rather due to one’s attitudes and behaviours. People who believed they were lucky differed from those who did not.

The self-described “lucky” people were more observant and open, had more extroverted personalities, a lack of anxiety, and were more optimistic. This led to more success and opportunities, which people saw as “luck”.

Reframing – Rejection? What’s that?

When I asked Matt how he felt during the times he was rejected by a woman, he said “Unless you think she is going to be the mother of your children, move on.”

While most men are busy trying to prove themselves to women, Matt holds off until he figures out if she is worth it. This isn’t arrogance. He is simply aware that not everyone is worth his time. Matt also believes that rejection is part and parcel of being a single guy, and that if you never ever get rejected, all it means is that “you’re aiming too low”.

Never take rejection personally. Most of the time, her reason for rejecting you has absolutely nothing to do with you. She may simply be in a bad mood, have a boyfriend, or you’re just not “her type”. No big deal.

Worth – Love yourself

Confidence stems from a strong sense of self-worth. Matt knows exactly who he is and what he’s worth. For example, once, a friend told him his jacket looked odd and wasn’t flattering. Less confident guys would probably feel offended or self-conscious. Matt simply laughed, looked at himself in the mirror, and said “I like it!”

He moved on like it never happened. He didn’t get defensive, and he certainly didn’t feel less attractive because of the comment. You can never truly be confident if your sense of self-worth hinges on what other people think of you.

Down-to-earth – Humility is a virtue

Despite having a great life and being good with women, Matt never name drops or brags about himself. Here’s a fact -- women can’t stand men who talk about themselves and their success. A man who feels the need to “tell you what he’s worth” is a huge turn off, even if he really is successful. Women read it as a sign of insecurity.

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Identity Capital – Be interesting

I asked him, “What would 35-year-old Matt want to tell 15-year-old Matt about dating?”

His answer? “Read a lot, about anything and everything, so you are better armed for the conversations ahead.” I fully agree.

Identity capital is what we build up when we invest in ourselves. It is a culmination of all the skills and interests we’ve cultivated over the years. Even your sense of humor is built up this way. If you had spent a little time building on it since you were a child, by your thirties you’d be rich in identity capital.

This is the stuff that comes into play when people ask you, “What are your passions in life? Tell me more about yourself!” I’ve met too many people who have absolutely no answer to these questions. If you want to be an interesting person, it’s time to build your identity capital.

Knowledge – Being well-prepared

In business and marketing, we’re always taught to know your target market. If you don’t understand your target market, you will never be able to sell your product. In dating, the same applies. The target market is the group of women you’re interested in, and the product being marketed is YOU.

Matt applies this principle to his approach. Before he begins courting a female, he’d gather as much as information about her as possible, and make educated guesses about what she’s like. Armed with this information, he is able to execute an approach that gives him the best chances of success.

For instance, he once surprised a girl on a date by taking her to a masquerade instead of the usual dinner and drinks. He also did research and found out that her favourite travel destination was Venice, and presented her with a beautiful Venetian mask during their ride to the party. What he did showed creativity, initiative, confidence, and effort (my next point), and this set him apart from other men.

Effort – Give her a reason to stay

With the onslaught of dating apps, dating has simply become a numbers game, with everyone grabbing on to the lowest hanging fruit, and then realising that it isn’t what they want.

Effort shows that you can be bothered. Effort shows that you care. Effort shows respect for oneself and for others. Regardless of whether you’re single or married, at work or in a friendship, making an effort is the best way to show someone that you’re a person of substance.


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Wendy Tse is founder and head matchmaker at Society W, a boutique matchmaking consultancy targeted at Asia’s elite single men and women. When she is not implementing online dating strategies and helping them find love, Wendy is committed to changing mind sets and removing the social stigma surrounding matchmaking in Asia. She currently resides in Singapore with her husband and two pet dogs.

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