Why did he keep asking me if I would like him if his friends weren’t assholes to me and he wasn’t?

So I told this guy I used to like him in grade six. After I told him he started asking me questions like if I would still like him. I told him no because it’s true then he asked why I told him because his friends.(they are completely assholes to me) then he said if his friends never existed and I never knew them same with him would I still like him. Once again I said no. He kept asking me. And saying if he wasn’t a asshole to me I would still like him. And also asked me if he wasn’t a asshole to me if I would still like him.
Why did he keep asking me if I would like him if his friends weren’t assholes to me and he wasn’t?
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