Can't send iMessages to 1 person unless they message first
I have ios 9.3.1, i've restarted my phone, deleted the conversation numerous times to start a new one, made sure my iMessages were set to my phone number and turned on "send as SMS" which also is giving me issues with this one contact. If the iMessage won't go through it shows it goes through as a text but he never gets them. I don't have him blocked and he doesn't have me blocked or else his iMessages would never come through to me throughout the day but I cannot text him without him texting me first. It'll randomly stop working sometime during the conversation. It's frustrating and started a week ago. He did just recently get the iPhone and we had the issue last year when I first got my iPhone 6 but it resolved itself within days now it's happening again. I need it fixed he lives 7 hours away and he's my boyfriend so please help!
iPhone 6, iOS 8