IMessage on iPad 2 with WiFi: can receive but can't send

On my Dad's iPad II with WiFi, when he sends an iMessage to my iPhone it is marked as "Not Delivered" (and does not arrive) but he receives them from me and I can receive them from others.

Hi there Twinklefingers,
According to the article below, if the issue is only present with a a specific conatact, you may need to delete that messaging thread and create a new message. If the issues persist, take a look at the article for additional troubleshooting steps. 
iOS: Troubleshooting Messages - Apple Support
-Griff W. 

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