How can I figure out if he's ready to move to the next step?

Anonymous
I think I have a pretty solid friendship with the guy I've been talking to for the last few months, but it's gotten to that point where I don't really want to sit around and wait for him to ask me out, even though I think mutual feelings are there. Problem is, I'm too shy to do it myself. Are there any specific ways in which I can steer the conversation or certain questions I can ask him that hint to him that I'd like for him to ask me out?
How can I figure out if he's ready to move to the next step?
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