It does look weird yet because I am not used to it right now but I do see something awesome in this.
And regarding the smilies: Why wont you just add another option to toggle the smilies on the clientside?
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I like the idea, especially adding it so you can attach pics. Maybe make it you can also attach other files such as songs and such. Nice job Andrew.
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How do you plan to attach songs? You can simply send the YouTube link which would be less laggy I gues.