Last night we closed the cats out of our bedroom so that Chris wouldn’t bother us, but I’m not sure if he bothers us more in the bedroom or outside the bedroom. Shortly after we closed the door, Chris started scratching at the door and crying that desperate cry of his. We tried to ignore him but he just wouldn’t stop. After about five minutes of constant crying and scratching I couldn’t take it anymore and open the door and let him in. I don’t know how he does it but he always wins.
After his initial pesty behavior of scratching my face and biting my nose, I moved him to the side. Surprisingly, he behaved for a while. I was able to fall asleep but by around midnight Chris couldn’t behave any longer and started bothering me again. This time he didn’t bother just me, he had to bother Rose too, who insisted that I put him out.
That worked and we were able to fall asleep, but early this morning he was crying and scratching at the door again. I was concerned about what all the scratching was doing so when I turned on the light and looked at the door, I saw scratch marks along the side of what I believe is the original 120 year old door.

The problem is I do not know what to do about Chris now. I do not want him ruining this door but I also don’t want him ruining my sleep. I thought about putting a metal plate and the door where he is scratching but putting screw holes in the door can be almost as bad as the scratches.
Ideally, I would like to train him to not be so annoying but it is in his nature. You would think that he would eventually realize that when he digs his claws into my face I get upset, but he never seems to make the connection.
What do you think? Does anybody else have this problem?