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I always use smilies - even to those I would never be attracted to. It is just something I do if the topic is a bit serious and I need to lighten up a bit or if I think that people may take my e-mail too seriously or take offense to it.
I don't think that any emoticon in an e-mail at work should ever have be looked at as someone flirting with you. You need to depend on body language to know whether that is the case.
Whenever my partner sends me a 'shop talk' email, it is always followed by a knowing smiley. And I know what this means
There are exceptions to this rule. For instance, if you and the female are not married and have not had sex before then it will mean nothing at all. People attach smilies to emails all the time and would be horrifed if anyone took it to mean anything other than a smiley
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