I love emoticons -- as any of my co-workers will confirm. :-) When I find icons that I like, I add them to an emoticon palette. When I run into a situation that feels like it needs an emoticon (someone going on a vacation to the beach, for example), I find an emoticon that I can use, and add it to the chat.
One preference you can set that makes it super easy to use emoticons is to set a short-cut key for your emoticon. Here's how this works.
1. Add the emoticon to an emoticon palette. You can do this in Preferences - Emoticon Palettes - Add Picture:
2. Now, with the picture added, enter shortcut text that you can use to bring that up. For example, suppose I add this picture to my emoticon palette:
To make it easy to insert this emoticon into my chats, I just specify a shortcut that will cause this emoticon to display. For example, let's say I want this emoticon added whenever I type "/wh". I can specify this in that same Preferences page, as the keyboard text:
Now this emoticon will display in my chat whenever I type "/wh".