There’s a long standing cliché when it comes to bars and clubs of the so-called pickup line.  Anyone who’s ever heard one–one choice example being “hey baby you must be tired, ’cause you’ve been running in my head all day” knows how awful they are, and completely useless for anyone actually trying to meet girls.  Yet, many people make the same mistake when it comes to flirty text messages, sending something cringe worthy instead of witty and effective.

I went Googling to see what messages I could find posted on the web.  Let’s look at three basic types that I found:

1.  ”I wish I was a teddy bear, that lay upon your bed, so every time you cuddled it, you cuddled me instead.”

Believe it or not, this was the first flirty text I found posted at a website.  It’s just as good as your old-school pickup line.  Read:  absolutely terrible.  It’s a cheesy statement, puts way too much value on her, and unless she absolutely loves you already, it’s going to turn her off completely.  Forever.

Score:  0 out of 5.  Hopeless.

2.  ”Stop thinking about me!:)”

This one has promise, but needs a little work.  The tease behind it is a good one–rather than be gooey and complimentary towards her, it casts the guy as the cool one–but puts too much emotion in.

Note the “!” followed by “:)”…this screams forced joke to the girl.  If you’re going to use something like this, you need more tension.  Look at how it reads without the punctuation:

“Stop thinking about me”

Look too harsh to you?  This would work really well with some girls, but runs the risk of alienating some.  Here’s a happy medium:

“Stop thinking about me ;)

This communicates that yes, you are joking, but without reaching too far emotionally.  Just be sure that if you do use this, lay off on further smileys for a couple texts.

Score:  3 out of 5.  Reaches too hard, but a small tweak will make it much stronger.

3.  ”Those beautiful eyes, that incredible body, such a brain, a sexy mouth, nice smile …. but that is enough about me, tell me how you are?”

This one…is actually good.  Note that it starts as if it’s going to be some cheesy over-the-top compliment, that would be guaranteed to fail, but then ends with the reversal.

Score:  4 out of 5.  The only way to make it better is to tailor it to her using callback humor or an inside joke.

This one hits the right buttons:  the guy is being funny without forcing it, he’s putting her on the spot somewhat, and it’s also noncommittal.  One trap you want to avoid with flirty text messages is sending something that makes it seem like you need her to respond, because if you do that and she doesn’t respond, you lose value in her eyes.

It’s much better to send one-off flirty text messages where if she doesn’t bite, it’s not actually a blow-off.  You were just sending something casual, and it doesn’t matter if she doesn’t respond.  That’s the problem with sending a girl something like “hey, what’s up?”–if she ignores it or takes 8 hours to respond, it’s a clear blow-off to you.  Keep the texts light and funny and you’ll avoid that trap.


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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Here’s the deal:  you met a cute girl at the bar or a party, got her number, and it’s time to text her.  The question is, how do you convey the right flirty attitude without being cheesy or too emotional?  We’re going to take a look at a few elements of the art of good flirty texts.

First off, let’s look at what a good flirty text isn’t.  We’re going to look at some examples of bad texts, with the situation of a guy who just met a girl and is trying to get something going.  Disclaimer:  I don’t pretend to have sent these myself, but I’ve had female friends show me the embarrassing things guys have texted them.

1.  hey sarah, it’s john…we met at Generic Bar #3 fri night.  you seem really cool, we should get a drink

What he’s trying to do: “john” isn’t really sure what to say, so he starts by reminding Sarah where he met her, then he’s complimenting her and asking her out.

Why it doesn’t work:  you should always assume the girl remembers who you are (you did put her name in your phone, right?  if not, start doing that every time you get a number).  Beyond that, going right into flattery and asking her out isn’t going to work unless she’s 99% sure she likes you, and most of the time, the girls you meet at a bar or nightclub is going to take more work than that.

2.  hey grace, great meeting you…you said you like jazz, we should go to that new jazz club on Z St

What he’s trying to do:  our luckless protagonist is starting normal enough with Grace…but then wants to show rapport with her by referencing back to their conversation and using that ask her out.

Why it doesn’t work:  there’s a funny catch-22 with remembering what girls say to you.  On the one hand, they always say they want a guy who pays attention…but on the other, the more details you remember about them early on and then parrot back to them, the more likely they are to cast you into the stalker/creeper role.  Unfair as it is, you want to avoid this.  The only time this text would work is if they had already agreed to go to that jazz club, and even then he’s better off going about it differently.

3.  yo beth, steve here…what’s up?

What he’s trying to do:  casual as can be to start a conversation.  Steve thinks this can lead to a back-and-forth talk, and he doesn’t even have to send something that looks like a flirty text.

Why it doesn’t work:  he’s asking Beth to carry the conversation.  If she’s reasonably into him she may reply…but if she has any doubt, she’s going to ignore this text, and when she would reply, most responses would require him to ask more questions to keep it going.  It’s a weak way to start texting, putting him at a disadvantage from the beginning.  

These examples may or may not seem extreme to you, but I can tell you right now that men I’ve known–and myself in my more naive days–have tried to send flirty texts and instead came up with these.  And yeah, you can write these much better…but if you have the same basic flaws–trying to flatter, trying to force commonalities, and relying on her to make the conversation happen–you’ll still run into problems.  Next time we’ll start getting into just what makes for solid flirty texts and show you a better way.


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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