Item assignment is based upon who is holding - or last held - the items. Making them over to your friend does not magically transport them to him. He will have to journey to wherever it was you left them, and pick them up himself in order for them to be assigned to him. The fact that you gave him ownership means little, in practical terms.
"May the Grace of Ara go with you, and His Vengeance be wrought upon your enemies."
Yes, he needs to go to the location at which you left the items. And yes, if that happens to be out in the open or in a publicly-accessible facility, someone else can come along and pick them up. It is indeed best to give him items yourself in person to ensure that he receives them.