Advice from a Matchmaker: How to Win & Lose at Online Dating

A lot of people forget something crucial about online dating: It isn’t an end but a means to an end. And what’s that end? An offline date.

Let me repeat: Online dating is a means to offline dating. A lot of people seem to have forgotten that. Don’t be one of them.

Rest assured you are not winning at online dating if you are swiping right on everyone and you’re getting a tonne of right swipes in return.

You are definitely not winning at online dating if you have so many conversations going on you can’t remember who said what when.

And you’re 100% not winning at online dating if you have been chatting with someone for more than a week and neither of you has taken the initiative to set up an offline date.

This, in fact, is how you lose at online dating.

The way you win is by:

  • Knowing what qualities you want your future Significant Other to have and focusing only on the people who have them;
  • Matching and chatting only with the people who have the necessary qualities; and
  • Meeting IRL with these promising people and getting to know them.

You win at online dating when you meet quality people for offline dates. It’s only through dates IRL (in real life) you can experience each other fully and figure out if you have chemistry.

Ideally you will schedule a date within a week of matching online because you do not want to text for too long. Texting too long can give you a sense of false chemistry that will not translate to real life and you will feel disappointed because you’ve wasted a lot of your finite bandwidth on something that didn’t pan out.

Now, in Hong Kong, we are very busy people. We work crazy hours, have tonnes of hobbies, are very social and travel a lot. It is rare a date can be made within that first week of meeting because of conflicting preexisting engagements.

In this case don’t focus on dinner or drinks. Suggest breakfast, lunch or a mid-afternoon coffee if you work in similar areas.

But how about if you are both out of town?

My suggestion is to do a 15-minute Skype call.

Is that crazy? Maybe. But it’s worth it because Skyping will get several things out of the way, including:

  • Will prove to you that this person is real;
  • You can be assured that the photos they’ve used on their online dating profiles are what they look like today;
  • It will show you how interested in meeting they really are;
  • You can better determine chemistry;
  • Gets you that much closer to being IRL; and
  • If it goes well it will encourage you both to be more flexible with your schedules.

Obviously treat the Skype session like a date – keep your work clothes on, touch up your hair and tidy the background a little.

Remember: The only goal with online dating is offline dating.

Once you’ve figured out if someone isn’t interested in meeting you IRL you can delete that conversation and move on. The last thing I want is for you to catch feelings for someone who is only interested in a pen pal so I advise you to be ruthless about this. Within the first week of matching ask them to meet. If they give you excuses and don’t suggest a concrete alternative, delete the conversation and their contact details. You don’t need this pointless banter using up your finite emotional and mental resources.

xo Ariadna

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