I actualy never use winks and emoticons with girls. I think they look a bit needy. But some sentences on facebook and in text messages might look boring or emotionless while if I would say it in real life, a seductive smile and look might make the phrase more sexy.

For example, I want to send to a girl (not literally translated): "how loose did you get at [big party event]?", but I'm not sure wheter I should add a smiley, or keep it cool.

1) "how loose did you get at [big party event]?"
2) "how loose did you get at [big party event] ?"

What's the best of them? Just keep it cool with (1) (but maybe too cool?), or shall I go for the more open (2) (but maybe too open)? Do you prefer emoticons or do you rather not use them?

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Ambitious to be succesfull => Shyler

I think your thinking too much about it. Like how some guys think entertaining a girl is bad. If you don't do it don't do it, if you feel it fits use it lol. I use smiley faces all the time. It conveys the message your sending because a message can be taken out of context easily, an emoticon helps as a way of displaying the lack of body language. like for something dirty or being a smartass, I use em as a habit now but it doesnt kill my game. The choice of context will kill your game more than emoticons will.

I have red somewhere a long time ago that you should refrain from using smileys as much as possible. That's why I was wondering. I hate texting as I used to fuck a lot of things up with texting. I know it's a minor issue but a little bit more security on weaker spots is always welcome.

_________________
You WANT to make a change.
You CAN make a change.
You WILL make a change.

Ambitious to be succesfull => Shyler

I rarely use smileys. If a girl uses them a lot then I might throw one in. My advice is to stay away from text altogether, as much as you can. Only use it when you have something to say to them.