Interesting iMessage Problem between Macbook Pro/iPad 1

I was recently forced into getting a Macbook Pro (I would have preferred an iMac if I had to buy a Mac at all) and everything has gone as well as can be expected (background: I build PCs and am a Linux user. I am proficient in Mac/Windows/Linux with my preference being Linux > Windows > Mac) except one thing:
The person I talk to the most with iMessage has an iPad 1 and about 90% of their messages appear NOT DELIVERED (red !) immediately when they try to send them.  I can send them messages, and they receive them.  I've had one single message fail in the way their messages fail to deliver, but had no other problem with messaging anyone else or receiving other messages.
Any ideas?

Hi tristesse,
If you are having issues with receiving messages from your friend’s iPad, you may want to troubleshoot using the steps in this article -
iOS: Troubleshooting Messages
http://support.apple.com/kb/TS2755
Thanks for using Apple Support Communities.
Best,
Brett L

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    <Personal Information Edited by Host>

    HI,
    Quote.
    HI Ralph,
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