Your and his age are gonna be major variables here. Conversations and relationships work very differently at different life stages.
You sound like you’re maybe a teenager? Try asking interesting questions that require some thought to answer, but still leave room for your friend to give an easy thoughtless answer if they want to. Where do you think we’ll be in X years? What’s something you thought you wanted but as you’ve gotten okay have realised you actually don’t? What do you think we do now thar future generations will think is crazy? Listen to his answers and ask followup questions.
Personally, I’ve always been most impressed by directness, honesty, intelligence and courage.