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Feb 12, 2014 7:28 AM in response to esweesoby matt00,Hey esweeso,
Thanks for the question. The following resource provides troubleshooting steps for issues sending iMessages, including issues sending to a specific contact:
http://support.apple.com/kb/TS2755
If you are still unable to send or receive an iMessage, follow these steps
1. Make sure that the contact trying to message you isn't blocked in Settings > Messages > Blocked.
2. Verify that the contact you are attempting to send a message to is registered with iMessage.
3. If the issue occurs with a specific contact or contacts, back up or forward important messages and delete your current messaging threads with the contact. Create a new message to the contact and try again.
4. If the issue occurs with a specific contact or contacts, delete and re-create the contact in the Contacts application. Create a new message to the newly created contact and try again.
5. Back up and restore your device as new.
Thanks,
Matt M.