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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