Why can't one person receive my messages?

I've never had this problem normally all my messages go through fine and vice versa but only a few days ago, my messages haven't been going through although it says sent. I have an Iphone5s and he has a Samsung, his messages send fine to me but he doesn't get mine. Even sitting next to me and sending a text to him he doesn't get it, BUT it works for everyone else on both phones, what's up with mine?

I've tried deleting the conversation, his number, resetting my phone, turning my imessage off etc. But don't know what else too do.

Is he blocked by mistake
or you switch off your phone for a while and then switch it on
and turn off i message

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