How to make a guy feel that he's good enough?

Anonymous
I have a huge crush on this guy and he feels the same but apparently he's scared to make a move because he thinks I'm out of his league (I'm really not). I've been trying to flirt with him but I feel that either his insecurity is blinding him, or I might be really bad at flirting with him, I don't know. But how can I make him feel that he's good enough? And that I won't reject him if he makes a move?
How to make a guy feel that he's good enough?
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