IMessage will not work with one particular iOS5 contact

I just got my iPhone 4S and noticed that a friend of mine I texted is not getting iMessages, it remains a green text bubble. I can iMessage other contacts, blue bubble, and he says he can iMessage his other contacts but when we text each other it remain a regular text message. I know for a fact he's got an iPhone 4 with iOS5, I have iMessage turned on, he says he has his turned on as well. I've rebooted my phone but I'm not sure if he has. Has anybody seen this before?

Having the exact same problem! Have tried every solution I can find on the internet and nothing works. Just started happening last night.
iPhone 5s, iOS 7.1.2

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