At our pediatrician's 12 month lecture, he spoke about leaving your child having sep anxiety. He suggested to have the sitter come the day before for about two hours. Have the sitter be one on one on the floor playing with the child while you are home, but you are in and out of the room with them. That way he can have it fresh in his mind that they are a safe person.
I know you said he did fine with your friend... does she have kids? Would you feel less guilty asking her if you were to watch her kids as "payback"? Hope something works for you, because we all need a break sometimes
Re: *Jill*