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Friends's iPhone no longer receiving my Android texts

For years now I have texted a particular friend who has iPhone from my LG V60 android.  Just this week he has not received any of my messages.  Also if I start a group message, he is the only one not to receive it.  Two other people with Android have also texted him and he does not receive their texts either.  However,  there have been a few others with Android who have texted and he has received those.  I have done everything I can possibly think of to his iPhone that I found online as well as to my Android.  Also, just starting in the last 2 days, if I text him I get a text back saying, Message to ______________ deleted.  I am very frustrated at this point and hope someone can help, please.

Has anyone heard of this issue and found a fix?