Mastering the Quintessential Date

Which of the following options would be an ideal first encounter with someone that you’ve just met?

  1. Drinks at a quiet bar in Surry Hills for inner city workers on Tuesday night
  2. Dinner and then ice-cream whilst sitting on the seats facing the Harbour Bridge on Wednesday night
  3. Karaoke with his / her friends and then dinner as group at Darling Harbour on Thursday night
  4. Pre-dinner drinks at a bar, followed by a fancy dinner, movie and then a scenic walk around Circular Quay on Friday night
  5. Brunch in a bustling inner city café in Paddington on Saturday morning
  6. Light lunch and a coffee in a quiet café at Dawes Point whilst watching people go by on early Sunday afternoon

My answer will ALWAYS be…

Option (6) because I’m an absolute sucker for a view and if a woman is able to pick up on this without me directly saying it to her then I’ll slap out a 4.5 carat diamond ring for her – I’m a simple guy.

Nah, I’m just playing – it’s going to take more than that for me to fork out a 4.5 diamond carat ring. But yes, it’s always going to be Option (6) because the last thing I want to do is to organise some lavish date (I’m paying of course) and then realise my date is literally a dumb-ass. In other words, the conversation is completely one way, she constantly needs reassurance, she talks about the differences between full-cream milk and light-cream milk as her favourite pastime and she can’t decide on whether to get the skin-less chicken caeser salad with chips and the skin-less chicken caeser salad with chips – no, that wasn’t just a typo! Now Option (6) is what I consider to be a “preliminary date” because it is a no fuss option that allows me to get to know her the best. Since the preliminary date offers the quietest and most relaxing atmosphere as compared to Options (1) – (5), it also gives her the opportunity to really get to know me.

Put simply, the preliminary date is the date before the proper first date i.e. it is more of a casual get-together as opposed to an all-out first date. The purpose of this preliminary date is to decide whether or not you want to see that person again. Just remember that there is always something to be learnt from meeting someone new and that there is no such thing as wasting your time when this situation occurs. Even if at the end of the preliminary date, you realised your date does not possess any of the qualities you look for in a partner, you have just learnt what it is that you don’t want in a partner! At the end of the day, however, you want to make sure that your time is utilised in the best way possible. At the same time, your date most probably wants the same thing, so be considerate of this as this creates a win-win situation and that’s what we always strive for.

When it comes to striving for a win-win situation, your mindset is very important because you need to put yourself in a situation where you are genuinely interested in getting to know your date – getting to know someone DOES NOT mean thinking that he/she will make a good boyfriend / girlfriend or a good husband / wife. As soon as you start placing your date under a category, you will over-analyse and fail to realise any positive attributes that your date has. Now for those who are a bit more “developed” in the years i.e. those who are more interested in building their empires and for those who would rather take the batteries out of their biological clocks, the same principle applies in that before anything happens, you must first be genuinely interested in getting to know that person sitting opposite you before you set yourself any outcome(s).

Since a preliminary date takes place in a very relaxed environment, there’s less pressure now and hence, this gives you and your date the opportunity to get to know each other – such an environment creates the allure of two old friends catching up over coffee. Now this would be a stark contrast to Option (4) where a layer of formality is added by attending a fancy restaurant – I’m sure you don’t need me to elaborate.Just for this reason alone I would use a preliminary date.

In terms of another reason for using a preliminary date, there’s actually cost savings believe it or not. Since I believe that the guy should pay for at least the first two dates, I’m sure you’ll agree with me that you don’t want to spend your hard earned ka-ching on a first date that encompasses drinks at bar, dinner, desert, a movie and then tea but subsequently find out that you really have nothing in common with her! You might get lucky (rarely!) because she will be so impressed (maybe!) but that’s just giving your money away because you’ll believe your money will grow back on trees.

If you want to really impress your date, learn how to talk to her. Call me a massive ass-clown or call me whatever you want but I already know that you look good otherwise I wouldn’t have got your number in the first place and asked you out. So now on this preliminary date, I’m more interested to see what type of person you are. Now since your key objective on a preliminary date is to get to know her better, achieving this is as simple as asking quality questions i.e. asking open-ended questions that begin with “why”, “how” or “tell me about”. I could write an entire piece on how you would master the first date by drilling down on key open-ended questions that you could potentially ask but right now, the focus is on genuinely getting to know your date.

Obviously over time as you place greater emphasis on genuinely getting to know people, you’ll become a good test of character and this can be applied to all facets of your life. In addition to this, you’ll become so good at it that you only need an hour or so to know what that person is like – all you have to do is to just sit there, ask the right questions and listen because she has finally found someone who is taking a genuine interest in who she is. To borrow a few words from Sun Tzu, author of “The Art of War”, that’s what I call “supreme excellence”!

So how can women utilise this preliminary date and achieve supreme excellence? By doing exactly the same thing because the same principles apply – be genuinely interested to get to know your date and not worry about what the outcome will be. You’ve just met this guy, so stop visualising whether he looks good standing next to you as the groom, whether he’ll make a good father, and what your off spring might look like. None of this will happen unless you pay attention to him NOW and get to know him first!

As the wise old turtle Oogway said in Kung-fu Panda, “Quit, don’t quit? Noodles, don’t noodles? You are too concerned about what was and what will be. There is a saying: yesterday is history, tomorrow is a mystery, but today is a gift. That is why it is called the ‘present’.”

So what’s one question that I love asking on a preliminary date?

“So are you good kisser?” Obviously you need to keep a very straight face here and having “balls of steel” would help. Although I love a woman who knows how to plant a nice juicy kiss, I’m more interested to see how she reacts. It’s definitely a very bold question and as Martin Luther King Jr. says, “The ultimate measure of a person is not where they stand in moments of comfort and convenience, but where they stand in times of challenge and controversy.”


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