Once he got out of the jail cell, he thought the game was dumb because his fellow cell-mates weren't fighting back. He ran past the bonfire and tried fighting the asylum demon with his broken sword. Needless to say he died and called me for help.
Once he got to Lordran the first path he chose was through the graveyard. After being killed by the skeletons a few times he called me again and I led him to the first bonfire near the Taurus demon. He killed the undead merchant because he thought he was an enemy, was killed by Havel, and then killed by the black knight before he finally got to the taurus demon. The Taurus demon killed him a few times, and after he finally won, he got to Solair and killed him for his armor(which he apparently didn't drop).
Surprisingly he managed to get past the Helkyte wyvern without being burned to death and kicked down the ladder to open the shortcut. He was then killed by the rats once, and then the boar over a dozen times.
He is still struggling against the Balder knights and hasn't even gotten to the undead parish bonfire.