There is a certain yin and yang to using wit in a flirty text:  a little bit can be funny and attractive, while a lot paints you as approval-seeking.  If a girl is really into you she won’t care, but someone who’s on the fence about seeing and/or dating you can be easily turned off by excessive wit in texting.

The good side of wit is that it can be a funny way to establish contact with a girl.  Let’s say you haven’t texted her for a several days or weeks and you want to reconnect.  Here’s a bad text to send:

Mike:  hey sara, what’s up?

Why is this bad?  Have a look at what not to text for some pointers.  Here’s something more effective, which I used with a girl who I hadn’t talked to for a week after she had gone on a vacation:

Guy:  operation:  igloo mountain is proceeding.  the ice is lined up and a stick barricade forming…just need something to top it off

I sent that one after a recent snowstorm locked me inside my house for a day, and got this response:

Girl:  hahaha!  that’s amazingggg!…guess who had to risk her life in ice for jury duty this morning?

Why did this work?  First off, I had already made a positive impression on her.  Without that, no matter how good you are texting, it’s going to nearly impossible to get her out.  At the same time, she had been on vacation with no cell for a week and the connection was fading.

If I came at her directly, it could have turned her off.  Instead, I sent something with a little wit that looks like a mass text.  This protects me from her “blowing me off” if she ignores it, as it’s not obviously directed at her.   I’ve used that strategy multiple times with tough to reach girls, where I’ll keep sending texts like that every week or two until I catch them in a receptive mood and they bite.  Like going fishing.

Anyway, after that I immediately dialed down the wit…I still bantered a text or two with her, then I got to the point and made plans.

Now then, let’s say I didn’t stop being witty.  If I kept up the igloo joke for another text it might have still worked…but I’ve seen guys (and my younger self) fall into the trap of just keeping the jokes coming, like a one-man laugh track.

That doesn’t work.  Girls may keep giving you lol’s and smiley faces, but the fact is you quickly put yourself into the category of entertainer instead of romantic prospect.  I’m in this to see girls again, and not just in a friendly way, so I’ve learned to temper the wit.

My rule of thumb is I can use a joke or observation to kick off a conversation, and maybe every 2 or 3 texts I can drop another one in if I need to up the energy.  Generally speaking though, if you stick to the basic rules of sending the flirty text you can get optimum results with just a dash of wit and then getting on to planning the meet.


Interested in how to send flirty texts and be successful with seeing her again? Check out this book, which takes you through everything you need to know about what to text her, when to text, and how to handle her both when she’s already into you and when you have to do some work to get her interested.

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