I don’t think it’s your picker I think it’s you. My advice is to try a gentler approach. Don’t change who you are but just try to back off a little bit and experiment/see how that changes the dynamic, then work that in to your regular style.

Not every point needs to be driven into the dirt. Not every sad story feeling needs validation. There is so much nuance to it. Just try something different, take a min before responding, let there be an akward silence, so he can think about how much he likes you or what he wants to say ect

More importantly, don’t just “be yourself” but give the other person time and opportunities to lead the discussion and show you who they are. Instead of it being sort of a response to you, letting it come about it’s own just to see.