BigTazz90: Any idea on how to remedy this?
Yes, keep your list under 255. 256 is an important number to a computer and WGT didn't allow for it with the Friends list. Anybody added after 255 will do exactly what you're seeing (or not seeing.)
What you need to do is edit your friends list and remove old, inactive ones. There's no fast way to do that, either. The most effective way is to go to your profile, expand your friends list, right-click on the avatar and open in a separate window. Do this as many times as you want and then go to each page, delete the friend and close the page.
Your new additions will now act accordingly. :-)