Text messages not sending

I’ve been trying to send a message to a single person and it’s not going through, I can get his messages and see him typing but he isn’t getting mine and it’s not even saying it’s delivered, we both don’t have eachother blocked and last night we could call but not text and now we can’t even call or anything. I’ve tried deleting the contact and I’ve tried removing the message chat I’ve tried everything I’m very very confused.