When you chose to listen to your friend and ask questions rather than counter every argument, you were basically putting Newton’s Third Law… the one that basically says for every action there is an equal and opposite reaction. Come at somebody belligerently and they will likely match that belligerence. Come at them with an open mind and with questions, and they will probably eventually, meet you with the same thoughtfulness. Will you reach agreement? Perhaps change a mind? Rarely. But you’ve opened the door for them to admit they are not 100% all in on their side and when their guy finally pushes things too far for even them to accept, they realize there is an open door.