I’ve hinted at my feelings about emoticons elsewhere, and it’s time to get into them in detail.  The problem is that many men use them like women, which just doesn’t work…for anyone involved.  They definitely play a role in flirty texts, but you must use them carefully.

The first factor is the simple case of what emoticons to use.  There are a few that no guy over the age of 12 should touch, and others that can be used effectively but sparingly.  Here’s a rundown of some of the most common:

1.  :) — The generic smiley.  This is one that 98% of the time that you want to use it, you really shouldn’t.  It’s not terrible in of itself, as it isn’t as over-the-top cutesy as other smileys, but it rarely gets you anything and risks making you seem too emotional/needy.  The one time I will use it is if I’m picking up a conversation with a girl I haven’t talked to much when I got her number, or if I’m bringing an old phone number back from the dead.

Think of it this way:  the smile on your face as you send that text should be a smile conveyed in words, no symbols needed.

2.  :D — The over-the-top smiley, and all of its brother and sister smileys.  Avoid this like the plague…it’s way too emotionally reaching, and will instantly drop your attraction with most girls.  I’m being serious–it may sound minor to you, but girls will note this.  Even if her every other text uses an extreme smiley, do not use one yourself.

3.  ;) — The wink, which is the one emoticon that has a place in the player’s repertoire.  When it comes to texting, your messages have a high risk of being emotionally flat…you only have 160 characters to work with, and it’s hard to convey sarcasm and teasing well with words alone.

You may use the wink sometimes–no more than once or twice in any one text conversation–when you really need to drive home a tongue-in-cheek comment.  I save it for when I’m teasing her, and occassionally if I need to drive home a joke I’ll break it out.

The art of flirty texts is not complete without emoticons, however, they are a tool best used rarely, and only with certain ones.  The one exception:  if you break a rare smiley that no one else uses, it can have a strong effect and is unlikely to hurt you.  But again, keep it as an occasional spice to your texts rather than the main dish.


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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