Since my text status to them reads "Sent" and I have requested a delivery receipt for their texts which only reads "Requested", do you think the problem is on my end or theirs?
Your friend should delete their cache and data within whatever texting app they want to use.
I haven't been able to check but I wonder if they aren't receiving my text because they have never deleted my hundreds of old text. Is that possible?
It is. If they want to save the thread back it up to a cloud service. Then delete the cache and data from application manager.
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