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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Last time we took a hard look at ways to not send flirty texts…and now we’re going to get started with the right way to send a flirty text to a new girl that you just met, say at a bar or party.  Now, I’ll talk about timing when to send this text later…but for now, just understand that you should text relatively fast, within 24 hours for cold approach (ie meeting a new girl at a club) and up to 48 hours for someone you met through friends.

The point of this first text message isn’t to get into a long conversation–we’re going to send her something to cement her memory of us, and also gauge how interested she is right off the bat.  

Alright, so it’s time to send the first text.  What to say?  There are two reliable ways to go…
1.  Callback humor:  any time you have a good flirty interaction with a girl–and if you’re not doing that, then fix that problem before you even worry about texting–you should have a good inside joke or two come up.  For example, if you find out a girl grew up in Texas and used to ride horses…you can nickname her “cowgirl”.  When you send a first text to her, you can use something like “hey cowgirl, better get to bed early…you need to feed bessie in the morning ;)

The trick to good callback humor is to find something that playfully recalls your conversation.  Don’t abuse it however, you should at most use it every other time or so when texting her.  Too many repetitions will play the joke out.

2. The generic non-needy goodbye:  this is a whole order of magnitude weaker than callback humor, but can be used if you have nothing funny lined up but need to make that first text.  I’ve had good success with this tried and true:  ”Nice meeting you, have a good night.  ~(my name)”  

It’s bland as all hell, but has an effective test built right in:  if she won’t bite on this, then you didn’t get enough initial interest on the first meeting to come out for a date anyway.  When she responds, don’t expect much…but the more emotion she puts in her response–such as extra emoticons or punctuation–the better a first impression you put on her.  This will tell you where you stand with her, and you’ll then follow up with something better later on.

There are some of the basics for sending a flirty text to a new girl.  The best approach is to use a little wit and nail some callback humor to her, as when you can reference the conversation in a funny way, it’s going to put her back in social mode and remembering meeting you.  If you can’t do something flirty based on that, your next best approach is the generic–but not overly emotional–polite greeting.  While that won’t build attraction, it will not cost if she’s already interested in you…and will also give you a good idea how likely she is to meet up when you text in the future.


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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