Iphone sending iMessage to all but one of my contacts, what's going on here?

So my friend and I can't seem to send iMessages between our Iphones.  I have tried to delete their contact information and delete all the past conversations we have had and re-added them to my contact list.  They can send me iMessages just fine.  I should also note that I am the only one on their contact list that seems to have this issue.  They are able to recieve iMessages from everyone else.  When they were living in Australia we did not have any of this issues.  However, since they have returned to Canada and set up their plan, suddenly I can only send them text messages.  We do not have this issue with anyone one else on our contact lists, this is an issue that exhists only between our two phones.  How can this issue be fixed?

Does anyone in the community know the answer to this ?
Alternatively - which email address should I direct this to to get an answer from Apple?

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