Smartphone Questions? Ask A Smartphone Technician for Answers
Can you tell me what kind of phone they have?
Ok, so you both have iPhones?
Does your conversation in Messages still list it as a group conversation? Also, what color after the messages when sent, blue or green?
try sending a message to your friend from the Contacts app rather then in Messages.
locate and view his entry
tap the Messages logo next to his phone number.
Then try sending him a message.
Ok, when you did it, did it create a new conversation in Messages or add your message to the previous conversation?
Do you need to save the old conversations or can you delete them?
Ok, please delete all conversations with him and any group conversations he may be a part of...
Then, restart your iPhone.
Finally, try sending him a new iMessage.
Messages to other iPhone users work fine, correct? If so you should only need to delete his.
Good. So you have deleted the other conversations. Did you try sending a new one afterwards?
...but it still doesn't indicate it's been delivered?
Can you find out what version of iOS he is running on his iPhone?
From the Home screen he can;
On the About screen, look for the "Version" information. Please let me know what it says.
Have them verify you are not blocked by mistake;
they can tap Settings
Verify "Filter Unknown Senders" is turned OFF
then tap Blocked and verify your phone number or Apple ID are not listed.
That's ok. You can return to this conversation at any time with that info.
At the moment, since all other texting works for you then I do believe this is a specific issue with the other phone rather than an overall problem.
Apologies for the delay in replying, I was away from the desk.
When you come back to the site, you should find our conversation under "My Questions". If you supplied an email address when signing up then you are likely receiving email notifications about our conversation as well.
If you can call and he answers then it's unlikely you are blocked but this seems to be an obscure issue.