Evening gentleman,

The tl;dr- should you ever tell a good friend he his being used by the women he dates?

I have a friend. He has been a buddy from high school and always loyal. Recently he has jumped into the online dating scene. Most will know where this is going.

His first girl, I met with another red piller. We both determined in the first hour she was using his inexperience to milk his high paying job. He would buy meals, tickets, and even hundred dollars of gifts for her. Then when he was sleeping, tried to hook up with one of us. (we shut her down) We did not say anything because neither of us felt it our place as they broke up soon after. We both are sure she never paid him back for some things she "owed" him for.

He is now dating a single mom. This scares me. For all the reasons we have come to find. He has been quietly spending all his time with her. I have no idea if he has been helping her with the child's needs. Should I impede in his business or let him learn his own way?