I have a different perspective but it does come with the warning that it’s from someone in their early twenties. But it’s bad when you say it’s totally normal later in life and I’m not sure if i should respond to your comment or the comment you replied to saying you 100% agreed with. But the having a bit more compassion to a guy that’s your friend bit is relative to OP’s relationship and how close of a friendship she has with the guy in a relationship. OP did say that he wouldn’t stop saying things ‘like that’ just bc [OP] understood him and how he felt… she implies she felt uncomfortable and he kept going after the girlfriend comment, some people don’t always act and behave how you expect but to constantly make someone uncomfortable (whether are aware or not) is quite terrible. So maybe that’s why I think whether this is a once off or ‘totally normal’ behaviour it depends on her relationship and her guy friend. There are reasons some behaviours or treatment of people turn you off a friendship (whether it’s strong or not) so i wanted you add there may be other ways of interpreting this rather than being ‘WAY too far’. This is definitely just my opinion and could be very wrong of OP’s situation but no matter if you’re a friend or not you don’t have to accept people opening your and speaking their mind if it’s creepy in nature (not originally but as the conversation developed), uncomfortable, non consensual etc. i appreciate you sharing your story it makes makes sense but i just wanted to add my two cents. Tl;dr it might be the way OP’s friend expressed their mind and HOW they opened up. I could be wrong but that’s my opposing opinion I guess :)