Friends iphone isn't receiving my texts suddenly

Miembro

Hi, so I'm having trouble texting my friend but the strange thing is, I was able to text him before. He has an iphone (not sure which one) and I had a samsung at the time (now pixel 3) when it happened. He was able to receive my messages fine on my motorola and my samsung too, until he couldn't get them from my samsung suddenly. I recently changed phones and he still isn't able to get my texts through my pixel 3. I've tried inputing his number back in and even downloaded other texting apps, but nothing seems to have worked.

Please help!

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