Imessage won't 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 Wi-Fi, 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!

Please help iMessage won't send to normal messages

  • My phone won't send an iMessage to a person with another iPhone when it used to? Ok so me and this person text and we rely off iMessage cuz we both live over seas and iMessage used to be fine for both of us but now for her phone it keeps sending texts and it's costing me a lot of money. I have all my settings on and stuff and I can send iMessages to other people but to her it keeps sending them as a text when me and her clearly can iMessage cuz we both have iPhones. I don't know what to do and it's costing a ton of money for me, and prolly her!
  • My iPhone 5c won't send messages to one person. WHY? I will send a message a it shows blue for an iMessage and even that it was delivered but the person i sent it to never actually gets it. I'm not sure how to fix this and could use some help!
  • My iphone 4s won't send iMessage to one person? I'm trying to text someone, and it won't send the message. It doesn't say delivered underneath it or anything. My messages send to everyone but this one person. Why!
  • IPhone not sending iMessage to one person? So I put a friend of mine on do not disturb for a day or two to keep myself from texting them. I took it off and texting was fine. I just realized that a lot of the imessages I've sent him (since Sunday) didn't deliver and they did not automatically switch to text. Why is that happening? I don't believe he would block me he s my best friend. But it is possible.