2 iphone's 1 userid - does this mean imessage won't work?

I tried iMessage with a friend and it worked fine.
Now when I try to iMessage with another iphone 4 ( we are in different cities ) it doesn't work!
Does it matter if it is registered to the same apple id?
OBVIOUSLY - 2 different cell #'s etc.
Any suggestions? I turned off imessage and now we can text message again but that kind of defeats the purpose.
THANKS!

Do you have a messaging plan? If so, why worry?
FWIW, i have two phones sharing one apple ID and we iMessage without any issues.

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2 iphone's 1 userid - does this mean imessage won't work?

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