First I don’t really know this dude or how he says it so I cannot be 100% sure. But I will answer based on my own conclusions and experience.
Everyone knows that a person’s best friends know most things about them. Plus people usually confide in their friends especially about their crush/boyfriend.
Does he know you like him?
He probably was just trying to find out what you say/think about him. If he doesn’t know if you like him then that could be what he’s trying to find out. I will be honest I have done this before. A guy I liked a couple years ago he and I had a mutual friend who he talked to a lot. I used to ask her like had he said anything about me or do you think he likes me?
I don’t think it’s obsessive or creepy. But you know the guy and it is your opinion that matters.
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