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Twype (short for "Twitter to Skype") is a new Windows-only tray tool that can help you update your Skype mood on the fly without doing anymore than posting to Twitter, or listening to music.
All you need to do is download a small executable file, install, enter your account info, and you're ready to go. Once every five minutes the program will check your Twitter account and paste it to your Skype mood area. If you use Winamp, you can also set it to check to see what song you're playing, and that will be pasted to your mood. With Winamp, it checks every five seconds, and will override the need to check Twitter. Once you stop Winamp, it will revert to checking for new tweets.