Colloquy Emoticons edit the `menu.plist` file found here: /Applications/Colloquy.app/Contents/Resources/Emoticons/Standard.colloquyEmoticons/Contents/Resources

menu.plist

(
    {name = Smile; image = "smile.png"; insert = ":)";},
	{name = Frown; image = "frown.png"; insert = ":(";},
	{name = Wink; image = "wink.png"; insert = ";)";},
	{name = Happy; image = "happy.png"; insert = ":D";},
	{name = Stoic; image = "stoic.png"; insert = ":|";},
	{name = Cool; image = "cool.png"; insert = "8)";},
	{name = Razz; image = "razz.png"; insert = ":P";},
	{name = Surprised; image = "suprised.png"; insert = ":O";},
	{name = Sarcastic; image = "sarcasm.png"; insert = "9.9";},
	{name = Annoyed; image = "annoyed.png"; insert = ":\\";},
	{name = Angry; image = "angry.png"; insert = ":x";},
	{name = Relaxed; image = "hat.png"; insert = "d:)";},
	{name = Jamming; image = "headphones.png"; insert = "[:)";},
	{name = confused; image = "confused.png"; insert = "o_O";},
	{name = shockedfrown; image = "shockedfrown.png"; insert = "8-(";},
	{name = anime; image = "anime.png"; insert = "^-^";},
	{name = dorkgrin; image = "dorkgrin.png"; insert = "XD";},
	{name = evil; image = "evil.png"; insert = ">:)";},
	{name = kirby; image = "kirby.png"; insert = "<('.'<)";},
	{name = pikachu; image = "pikachu.png"; insert = "(o^.^o)";},
)