There seems to be a template in many men’s minds for how online dating should work.
They believe it should be the same like how you meet a woman in person. You start by asking how is she or how’s her day, and then small-talk your way into finding out more about her. And maybe guide the conversation towards a common interest after that.
Can this work? Absolutely.
Is it more effective over the long run?
I like to think today’s post in this series will give you the definitive answer.
As a person, I’ve always been naturally playful and mischievous. I tease my friends, I banter with them, and I am generally unserious unless necessary. I even say things sometimes to self amuse.
I am the same way with women.
But I’ve had times when I weren’t playful, and in those moments, the interactions rarely went any further after that.
That does not mean you’ll have women falling head over heels in love with you just because you’re playful with them.
There are other variables that can make or break your success too.
But everyone loves a good time. And it won’t hurt you or the woman if she enjoys your company, and your interaction with her is full of smiles and laughs.
It’s not just about having fun as well.
Research has shown it actually helps make the woman feel more at ease and comfortable with you.
Those positive emotions build trust. That helps her see you as an ally, someone who’s on her side… making it easier for the conversation to move forward.
People also unconsciously interpret playful behaviours as evidence of intelligence, creativity, emotional stability, social confidence and low aggression.
In simpler terms, it makes you look good.
For a long time, I wasn’t aware of this subtext. I was merely being my cheeky self and having fun at the same moment.
But because my brain likes to pick things apart, I started noticing my own playful behaviours, women’s responses to that, and how it affected my interactions.
Along the way, not only did I discover how to flirt better, I also turned being playful into a powerful weapon in my conversations on dating apps.
It is no coincidence or luck then, I eventually ended up on a date with Gemma after our witty banter on Tinder and Telegram.
We were simply two idiots indulging in fancy and pretentious wordplay.
But beneath the wordplay is the subtext that I am fun and good company. That I am quick on my feet and smart enough to keep up with her.
My mischief helped as well, since it was obvious she was the same. That’s why she said “… maybe I’ve found the osteopath of my dreams”.
The mischief and fun energy made it easy for her to want to keep things going.
“And how have you been a terror lately?” was her way of doing so.
We didn’t engage on an information exchanging level where we shared about each other’s day. We didn’t try to find out whether we had any common interests either.
It was simply a whole lot of playfulness and smart-assery.
Fun, enjoyable banter. That led to us flirting.
A natural consequence.
Because… when you make a woman smile and laugh and enjoy your company, she becomes open to the idea of flirting with you.
And Gemma allowed that to happen by saying she “just happen to have a spot empty beside me in hell”.
I flirted back with, “I’d love to sit beside you then. But we’re gonna take up 2 spots each. Just because we can.”
The vibe was already unlike other matches she’s had.
It was easy for me to pick things up again after that.
That’s why when I did, it was to suggest the idea of a date — “We gotta start terrorizing people together soon…”
You’ll notice it was a bit of a playful callback to our previous conversation, while leading the interaction forward at the same time.
Short and brief. But we made tentative plans. Nothing complicated.
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3 simple steps for going from match to date — the conversation game-plan behind this playful energy.
When I reached out again, it was merely to confirm plans.
She initiated it for me too — “Where is good for Tuesday? My last call ends 6.45pm or so.”
That’s what fun and playfulness can do. The woman is happy to confirm plans with you because she had a great time texting.
Then it was a matter of settling logistics for the date — time and place.
I kept the mischief going with… “More time to wreak havoc on others after that huh?”
And then on the day itself, I re-initiated the conversation — “See ya later at wine”.
More banter after that.
I sent her a skit by Key and Peele about two people miscommunicating via text, with Peele showing up wanting to bash Key’s head in with a baseball bat.
It was a gambit to get some humour going; getting the vibe up before the date.
That was it.
No flaking. Just a fun time texting leading up to the moment we met.
The date started well because of the texting. It was all smiles and laughs from the moment we set eyes on each other.
Conclusion
A lot of men think texting should be for arranging the date only, but women sometimes need a lot more than that.
You have to remember even without replying to their messages, they can still get hundreds of unsolicited invites to dates from the apps.
So they want to filter out the creeps and duds before taking things any further. It’s a self-protection mechanism.
The chatting is their way of doing so. And based on their experiences, most men inevitably “screw up” with time.
It may be the man misrepresenting himself because he’s not good at marketing his person, but in her eyes, she doesn’t see misrepresentation. She sees a mistake.
This strategy is not guaranteed to work in her favour, because women do make terrible choices sometimes. As we all do.
But it helped often enough for them to stick to it.
The best way to overcome that and their doubts is to make the interaction fun and enjoyable.
Because when they are uncertain, they flake.
If you give off good energy and have fun with them on text, it lends them more confidence they just might enjoy your presence in person.
And if the interaction is especially good, she’ll even anticipate the date.
I’ve had that happen to me several times where women will just ask me out instead of waiting for me to initiate.
This is not luck. It is what you can achieve when you know what you’re doing, and you do it well.
You can have the same results too.
Just by following the guidelines I’ve set out for you.
The best part? You don’t have to go through the hundreds of rejections I personally faced.
The question is… are you willing to adapt your approach and let your playful side shine?
