Imessage wont send to one person?

My boyfriend got a new phone number yesterday and when he sends me a text they come through as an imessage but when I send them back they automatically go through as a text. He has an iphone and so do I

I have tried turning imessage off, restarting my phone, signing out of my icloud account, deleting his contact and re-entering it.

any ideas?

Why does it matter? He gets the message.

If you're connected to wifi, your phone tries to do you a favor and save your text message plan. If you're not connected it should send regularly.
Hope this helps!

why do people bothering answering with stupid ass responses.