I can only respond based on my own personal experiences..
I have heard God tell me - FIRMLY: 'LET HIM SIT THERE!"
[I allowed one of my 3 best friends to sit where I was going to sit. Within 5 minutes, I watched in horror, as one of my best friends fell face-forward... he left for heaven within a few hours. This was the first time I ever knew God to speak directly to me.]
I have heard God tell me: You can't be friends with him anymore." [God had already prepared me for this, sharing something with me years before. So when I heard this as God's statement - I didn't question it for one second.]
During one prayer time, God brought someone up in my heart and spirit, and He asked me: "Will you pray for her? You do not have to pray for her. But, if you say that you will pray for her, and you do NOT pray for her... it will be counted against you!" [Still praying daily for her.. several times a day.. am in my 33rd year of praying night and day,,]
I have always tried to listed to what GOD tells me to pray, whether I understand it or not. It COULD be that God is protecting you about this relationship. BUT - at the same time... He could be using your heart and love and prayers - and teats - as a conduit for miracles to be brought forth.
I will kneel/pray/cry/intercede with you for this relationship....
you are not alone