Can't send iMessage to one person

I just got my iPhone 6 yesterday and its already giving me problems. I can't send imessages to one contact which happens to be my boyfriend. on my iPhone 5 which had iOS 8 it was fine but now nothing. it was working fine for a bit but just stopped working an hour ago. I tried rebooting my phone, restarting the thread, restarting all the networks, sending as texts, literally everything and nothing works. please help me fix this, out of every contact it's my boyfriend who just lost his best friend and I can't even text him back. I'm so frustrated and can't make my way to an apple store for another 6 hours.

Hi there katie22xo.
According to the article below, it looks like you may need delete the thread and create a new one.
iOS: Troubleshooting Messages 
If the issue occurs with a specific contact or contacts, back up or forward important messages and delete your current messaging threads with the contact. Create a new message to the contact and try again.
-Griff W. 

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