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How to Win at Dates

April 27, 2011

Recently I achieved something special: I successfully found someone on an internet dating website.  I’m not going to say I was lucky, because that would be misleading. Was Kasparov lucky when he beat Topalov in 1999?  Hardly.

Dating is ultimately a game.  I apologise for the reference to chess; that was misleading.  The game that I think comes closest to it, from my personal experience, is probably Sins of a Solar Empire.  Once you’ve dated for a while, you’ll see why.

I’m not claiming that I’m the best dater in the world.  But I’ve heard many people moan about how it’s not working out for them or how they feel they’re missing a certain je ne said quoi. I don’t think it’s arrogant to say: je DO sais quoi.

Here I’m going to avoid being offensive to homosexuals or women by referring to my date not as ‘he’ or ‘she’ but as ‘it’ (but I’m straight, so ‘it’ is a woman).

What Restaurant?

This is a balancing act. You want to go to i) the best restaurant you can think of (price considerations included) , which ii) you are happy to never, ever go to again.   Look, you don’t want things to ‘go Chernobyl’, but who does?   Fallout from a dating disaster can last many years and effectively lock off huge tracts of land.  I’ll put it this way: if you’ve been to the arcade in The Trocadero in the past 2 years, let me know what it’s like.

Early or Late?

You may be nervous for your first date.  To combat this, busy yourself until the time you’re meant to turn up, then embark on your journey.  Even then, don’t just approach your date. Get into a position where you can see it but it can’t see you (standard camouflaging and recon tactics apply).  Once it has arrived, wait a couple of minutes, then approach it.  If it asks a question about why you’re late just look straight into its face and say: “What of it?” 

What Not to Wear (or Be)

Don’t wear any of your normal clothes. Pretend that they have all been burned by some sadistic arsonist.  That t-shirt with that hilarious cartoon?  Burnt.  Those old jeans that finally makes you look cool?  Burnt.  There is a low probability that those clothes will impress it.  Instead, what you should’ve done prior to the date is make a crude assessment of its socioeconomic status.   Then go to the shop marketed at that status.  Look carefully at the mannequin.  Then copy it: buy all of the mannequin’s clothes.  Become the mannequin.  Hopefully your date will not say: ‘Oh, have I seen you before, lurking very static in the window of Primark, Oxford Street?’

And hide all your blemishes.  Your face should be as smooth and featureless as that of the mannequin.   I don’t think you get it yet.  On your first date you are not you. You are the appropriate mannequin.

Nice or Neg?

Be as pleasant as possible (but see below under ‘Do not smile’).  Compliment it.  But be on your guard: it may take an opportunity to neg you. I think everybody knows what negging is by now.  It’s when you say something like, ‘Hey, I like your mini-skirt, it does a really good job of concealing your unfeasibly large buttocks’.  If your date starts a subtle negging war, there’s only one strategy you can take: escalation.  And if you want to really stab the knife in (which works a treat) use this handy trick: let it talk and pretend to drift off, then come back and say nonchalantly, “Sorry, what did you just say?”

Test It

If you were thinking of buying a £350, 000 house, would you just let the smarmy estate agent show you around, all pleasant-like, and gush with approval?  No. You’d probe.  In the short-run, a date is more expensive than a house viewing, and in the long run the actual date-person is potentially more expensive than the house.  So probe.  I’ve found that, as a rule of thumb, dates don’t warm to direct interrogation.  But you should be slipping in at least ten good questions under the radar. I’ll give you an example.  I personally think dinosaur history is pretty important.  When I’m on a first date, I always ask it the question: “what do you think led to the extinction of the dinosaurs, and when was it again [I ask with sincerity], that they became extinct?”  If it hasn’t ever thought about this topic, I get the bill.  The specific answer doesn’t matter, it’s the ballpark that matters.

Try to make your questions as diagnostic as possible.  You are essentially playing a big game of Guess Who, where you’re trying to find The One, and you’re being charged by the minute.   So do you ask ‘Do you like puppies?’ ‘Do you like music?’  No.  That will allow you to swipe down no faces.    You ask, ‘Are you bald?’ ‘Are you black?’ ‘Do you have an egg-shaped head?’

What to Say

Think Guitar Hero.  Imagine a huge Talk Meter hanging between you.  Too much silence, and you fall off the meter.  Game over.  Too many dud notes ends the same.  From my experience, here are some topics to avoid: Religion, Politics, Dating (past), Dating (future), Videogames, Live Action Role-Play, Games Workshop, Science, Mathematics, Philosophy of Science, Philosophy of Mathematics, and Dinosaur History.

You should make a back-up list of Triple-A conversation topics and keep them in your pocket.  You should probably make your own up, but just in case you don’t have time, this is a brief excerpt from mine: Food, Books, The Weather, Funny Youtube Videos, Drinks, Ask About Its Family, That Time I Wore The Best Fancy Dress (Boutros Boutros-Ghali), How We Buried My Rabbit, etc. 

Don’t Smile

Just don’t smile.  Why would you smile?  You may as well push across the table a huge trophy engraved: ‘You Won.’

Here ends the FAQ.  I just want to say that I know this strategy works. I can say this because tomorrow I’m going on a second date, to Pizza Express.

* * *

PS I did draw a really neat piece of ASCII art to open this piece, but sadly it got lost in the creative tumult.

[Can I please say that I’m highly indebted to ‘Free Online Dating Advice’ for opening my eyes.]

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One Comment leave one →
  1. Pedro Cunha permalink
    May 30, 2011 12:30 am

    You’re too damn good, I’m glad I found you at the internet. Will show to all my friends in Brazil.

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