Why does my phone not always send or receive iMessages from certain iPhones?

My phone doesn't receive or send iMessages from a couple contacts I have and with other numbers it receives fine but sends as a regular text. I've played with all the settings but nothing is working

Aswell as needing an internet connection both devices need to be running iOS5. They also need to have imessage turned on withing settings>messages. If neither of the above is true then it wont work simple as.
iPhone 4 16GB, iPod Touch 8GB

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