Friend did not receive friend request

My friend Larraulton is silenced therefore cannot send me a friend request however he is able to receive friend requests, I tested it on another account and it worked fine, however it shows I have one pending to him, yet he doesn’t receive it from this account, and his silence doesn’t end until February, we have blocked each other and unblocked and I was able to send one yet again, but it didn’t work yet again.