IMessage won't work to one person?

My phone is sending text messages to someone with an iPhone. We used to iMessage together but he got a new phone and until he turned on his iMessage I had to manual send the messages as a text message. We'll he has all his setting set up, his messages come in as iMessages, and we can chat on my ipad iMessage to iMessage. But I can't figure out how to switch it so it will send him iMessages now. For the few days he didn't set up his settings I was sending them as regular text message. First it would not send as iMessage so I clicked and held the message and pressed send as SMS. After a couple times it just started doing it on its own and now that he can imessage i don't know how to get it back to trying to send it as iMessage first. My iMessage is on, in settings I have it switched to off where it says send as text if iMessage doesn't work, and my iMessage is working on my ipad with him and on my iphone with everyone else.

I've seen this before, make sure that the ios on the receiving phone is completely up to date, I was testing imessage on my mom's phone and it kept showing up green, I then noticed she hadn't updated her phone to the current iOs, once I did this the messages started coming in blue/grey

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