Stacey Krech

I understand your issue. We had a similar experience with my son when he was young with a neighbor boy who was a very bad influence. Look up Jordan B Peterson and his talks on the "Agreeableness" trait. I would guess both you and your son have a personality that is high in "agreeableness"? It appears in my life experience that a domineering strong personalty smells out the agreeable ones pretty quick. Your son enjoys making others happy and having friends. He doesn't want to say "no". Maybe he likes some strength he sees in a "Bob" type and wants to mimic it. I don't know. All I know is my son is agreeable...he likes people, is naturally very trusting, loving, friendly, and compassionate. It makes him an awesome spirit, but he got taken advantage of a great deal. Now at 14, he has learned this about himself and how to grow in personal strength and protect himself. The words of the Oracle at Delphi: "Know thyself". We talked with our son, helping him see how he was, where he was responsible for his own behavior, how others see him, and to decide how he wants to be in the world. Plus, how to say "no" and be mentally strong without becoming a jerk. Putting our son in Karate classes helped too. It gave him confidence and a way to play out that strength he craved in a healthy way. I would restrict his play with Bob to when there is direct supervision by you or your wife. Could that be uncomfortable? Sure. Do it in small increments then. Use a scalpel not an axe. Think on who's happiness is more important; your family's or Bob's? You are raising a future man. How would you want that man to be? Too agreeable and scared? Mostly I would talk with your son about himself, his possible weaknesses, and ask him who he wants to be...when he likes himself the best. The world is full of "Bobs". Teach him how to deal with them.