How to Start the First Message (Part I)


How to Start the First Message

I LOVE online dating. A lot of people believe that there is hardly any room to manoeuvre when it comes to online dating, mainly because you are missing out on body language. That is a very valid reason actually, but I’d also like to think that it’s all about creativity and how your mind is able to come up with the most random things at times.

At the end of the day, conversation is conversation. You cannot not know how to have a good one online without knowing how to do the same offline. That may sound like there’s a lot way to go for those who already have big conversational issues offline, but it’s really not. Conversation is something that can be trained, but it’s also something that’s natural to all of us.

More importantly, it’s also a part of lifestyle.

You cannot expect to get good at conversation without having friends, or having a life that involves only work and home.

For that reason, I do not encourage the use of pick-up lines. It would be easy, and some of them do work definitely. I personally have a custom line that works under specific conditions, but it stifles creativity. It’s a very good short-term solution, but we’re not about that.

What we want, is to train your mind so that it eventually gets really good with responding to people. Being smart, witty and funny are traits of an attractive man. A good way to start is to focus on your first message to the woman, on whatever dating site you may be on. It may seem tedious initially, but it’s really just getting your mind used to coming up with something interesting. As time goes by, you’ll realise it’s incredibly easy, and you’ll find your own style as your brain gets used to the process.

We won’t get into how you ought to flow in the conversation. That’s not the purpose of this series. What we want, is to provide you with a strong start, so that you see the possibilities that lie ahead of you. I always believe in taking small steps at the beginning, and each small success will motivate you to greater heights.

So let’s start.

How to Start the First Message

This was a message I sent out about 2 months back. To be honest, it was actually pretty easy coming up with what I wrote. I just had to put two and two together, and make it playful.

In her profile, she mentioned that she looked intimidating if she doesn’t smile. It helped that in her profile picture, she wasn’t smiling, so I decided to go along with the “bite my head off” line. We don’t wanna end it there though. That’s just a start to the overall message I am putting together, because let’s face it, that very first line can be rather rude.

I then linked it nicely with her nickname, which wasn’t anything flattering. In fact, her nickname seems to suggest that she might be up to no good. But we all know she picked that nickname in jest. I was merely playing along, and my “probation” line was really just to playfully push her away.

Now, the first two lines can make me seem rude. In fact, I wouldn’t be surprised if someone took offence. So, in order to show that I was merely kidding, I threw in that last line about forgiving her if she bought me food. It links up very nicely with her profile since she mentioned that she loves to eat.

Obviously, she knew I was playing. Her reply was short and sweet, but fun still. Which gives me something to work with.

How to Start the First Message

In this second screen-shot, I decided to go with the match percentage, simply because her profile didn’t really state much. She mentioned something about being able to fly. I decided to use that and play with it.

My first paragraph had a purpose – for my second paragraph to come into play nicely. With just the first paragraph, no woman is gonna reply to your message, unless you’re awesomely dashing. And it’s really a bit of a misdirection, because the serious tone deviated her expectations of what was to follow.

In my second paragraph, I went along with an old line about being a “half glass full kinda guy”. Again, that first line was really just for leading on to my “punchline”, so to speak.

Since she mentioned that she could fly, I figured hey, I’d love a ride. After all, who wouldn’t?! But we all know that’s impossible, so it clearly means I was just messing around with her. I then threw in that final line about grooming her wings for her, to suggest that, ‘hey, if you take me flying, I’d do something nice in return’.

The message isn’t humourous in any way, but it’s definitely interesting. On a dating site, not many men will message like this, so it’s a confirmed attention-grabber.

And as you can see, all I did was really just to get her interested enough to reply.

Her response justifies my messaging strategy. Add to that a good profile, and you’re sure to get a reply out of a beautiful woman.

Oh, as it turns out, she’s an air stewardess. Which explains her profile description about being able to fly.

In the next part for this series, I will talk about the purpose of the first message, deconstruct the mechanics of how to create one, as well as look into the subtext.

Stay tuned for more good times ahead!

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Next articleHow to Start the First Message (Part II)
Jiron's attention to detail has given him the ability to quickly pinpoint his clients' blind spots, allowing him to rectify their issues and helping them improve their dating skills at a much faster rate. When he is not busy with his clients, he spends his time helping old people cross the streets. In an attempt to impress the ladies, of course.


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