I have an old friend who has been struggling with relationships and her self esteem for a while. She has been relying on me quite heavily to get through it, for example calling most evenings and sometimes talking for hours. She once broke down in tears asking me why her current interest does not love her. Our lives are in quite different places, I live with my DH and we are expecting pfb in the summer. I think she comes to me because I have a different perspective to her other young single friends. We message everyday and speak on the phone most days. Today we had this conversation:
(No previous chat since yesterday)
Friend: Dating is the worst. Men are impossible.
Me: Are you ok? Did you speak to X or is this about someone else?
Friend: It's all of them!
Me: laughing emoji.
Friend: I've been thinking about my past. All men are bastards.
Friend: Except one.
Me: Who?
Friend: (The name of an ex boyfriend she dated for several years but they broke up 5+ years ago. He now lives with his wife and 2 children on a different continent).
We then switched to a phone call. I asked if she had been in contact with the ex today and whether that is helping her. She was pretty annoyed by my questions and insisted they're friends and he is a good person and she needs good friends now. I apologised for being judgemental and she snapped at me again. Then I asked if she is still in love with him. She yelled at me, told me it's none of my business, that wasn't what the conversation was about and then said she couldn't talk now and hung up.
I realise that I was extremely tactless to ask but I don't think it was an entirely foundationless assumption. Was I being unreasonable to think she might still love him? And, more importantly, was I being unreasonable to ask? I want to help her but I feel like we have the same conversation again and again and I don't know how to get out of it.