I wonder if he is insecure or doesn't care?

2 months ago this guy who met me in a party last October found me online and sent me a message, I didn't know him that well so I didn't respond. He started to come to my group event and I figured I can see myself date him. I started to text him, he always responds quickly. The convo is flirty and it can last for several hours till he goes bed. However, he never initiates text, and doesn't ask me out. Consider his personality that he lives to win and he doesn't like failure, I think he might be insecure, or playing the game so I can show how much interest. but at the same time I feel I am just finding excuses for him and he could just be uninterested, what do you think I should do to figure out?
I wonder if he is insecure or doesn't care?
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