Maybe our generation should be called Generation: You can just use a smiley.
Different smileys can encompass myriad emotions. They are, after all, called emote -icons for a reason.
Then you should use: If your sadness intensifies or: Then there are your ever-so-slightly more complicated emoticons — the flirty or silly tongue sticking out: But above all, my personal favorite has to be… the winky face. Is it a green light for hooking up? They will probably never fully understand every implication an emoticon has. From personal experience, my belief is that a wink from your best friend is the only wink that carries no implications and has no hidden meaning. A ;- from your crush can also potentially be devastating.
Say he has no idea you like him. Why did he decide to tell me that?
Is he trying to make me jealous? Does he want me to get mad? Should I just act totally chill about it? Should I tell him I like him? That is at least slightly more legitimate than worrying about what a wink means.