Imessage not working for only one contact all of a sudden

I can not recieve imessages from one contact. We have always been able to use imessage and just yesterday all of a sudden the only way we can text is if I turn imessage off. I can use imessage for everyone else and he can use imessage for everyone else, we just all of a sudden can't use it to text each other now.
I am reset my phone, deleted and added him again, and he has tried the same.

Hi,
On the Air, if you use the Apple Menu > About this Mac and then Click twice on the line that shows you the current OS version do you see the Serial Number ?
7:56 pm      Friday; May 30, 2014
​  iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

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