So why is “information exchanging” bad? Isn’t that how people get to know each other, by sharing information about themselves and seeing if they have any similarities with each other?
That may be true, but because it’s online… a woman’s attention is split between you, her other dating app matches, her real-life commitments and whatever’s potentially distracting her in the moment.
The good news is, her other matches are also likely to be “information exchanging” with her. That means if you’re doing things differently from everyone else, you’ll definitely get her attention right away.
How should we actually message our Tinder matches then, and make sure we get that date?
I will show you exactly how below, with screenshots from a real-life Tinder match of mine, Gemma (not her real name).
The very first thing you wanna remember when messaging your Tinder matches is…
Almost every man is going to start with a variation of the same type of messages:
- A simple hello (for the ones who believe conversations must start with a greeting),
- A compliment on her physical appearance,
- A question about the most obvious thing in her profile (for example, her tattoos),
- An observation about the most obvious thing in her profile, followed by a question,
- A pick-up line that’s often corny,
- Something weird/irrelevant to the both of them.
So the most obvious thing you can do is show up with something different. It may seem like a lot, but most men sound the same. That makes it incredibly easy if you just put a little thought into your opener.
And that’s how I opened with Gemma:
I built togetherness right from the get-go, by suggesting she and I will get along.
Then I delivered my punchline () by making a reference to her bio ().
I knew it would work simply because with online dating, if you can get her laughing right away, you’ll definitely get her reply.
She continued from my opener and the conversation felt natural almost right away, like two people who have known each other for a while.
This familiarity helps because it creates the impression the both of you get along with each other easily.
That impression is key; if our conversation continued so effortlessly, it will be much easier getting her number and then the date. I just need to lead her there.
So I used the word “wine” and “wouldn’t mind sharing” to set me up for later, when I want to talk about going on a date.
My message after that was meant to subtly agree with her, and suggest neither of us need to sell ourselves.
The set-up for the date worked well. She suggested I share the wine with her, which means I can move the conversation smoothly and easily towards getting the date.
She then added that she hoped I have interesting stories. All this conversation helps us paint a solid image of how the date can go, and that only helps the both of us feel good about it.
I continued leading the conversation by suggesting we share personal stories (), leaning into the image of a good date.
So when I finally ask for her number to arrange the date, she’s more likely to say yes instead of resisting or hesitating.
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A little backstory here. We were in the midst of celebrating the Chinese New Year, so I wasn’t able to reply as quickly as I could.
But because the conversation was going well, she double texted and , so we can move off the app and onto instant messaging.
And just like that, our interaction progressed forward effortlessly.
That is possible because I brought a good vibe to the conversation by starting well, and it was refreshing for her since it’s different from most of what she’s experienced.
Instead of boring and typical questions, or conversation that’s stiff and feels like it could stop any time, there was a light-hearted and fun energy, an ease to our conversation flow, and a natural chemistry.
That made it easy for her to decide if she wants to keep talking to me or not.
All I had to do from here, was to keep the same energy and she’ll definitely say yes to the date.
You may think this would be the perfect time to go for the date, but because of the festive season, I knew the date won’t happen so quickly.
I decided to do the next best thing — build more connection, so when date time comes around, she won’t flake.
The first thing I did on Telegram is a call-back reference. To let her know who messaged her, without having to say, “Hey Gemma, this is Jiron”.
This allowed me to keep the good momentum going, rather than breaking it and starting all over again.
Her response helped maintain the natural flow and easy chemistry we had previously. She proceeded to share her experiences vaguely. But it was very good feedback.
Now, if there’s anything I’ve learnt NOT to do on dating apps… it’s from understanding a woman’s experiences and perspective.
And what she said suggests most of her conversations are boring (aka banal), tiresome, and repetitive.
From her messages above, it’s obvious she often gets asked,
Having coached men for many years, I know very well what works and what does not. If you have the same conversations every single day, you’re bound to get bored very quickly.
That’s why you can almost never fail if your conversations are fun. Because it suggests that going on a date with you won’t feel awkward or uncomfortable, and gives her hope she may have met someone she can really get along well with.
In Part 3, I will show you how to keep this fun going, and secure the date easily.


