Getting him to come out of his shell

I posted here the other day about the guy i like but he seems to be shy and because of that i wasnt sure if he liked me. I have got my friend speaking to his brother and his brother says he thinks he does like me and wasnt surprised he hadnt texted me after our first date and told me i had to text him first. So i done this and of course we have been texting, i also invited him to go bowling with me and my friend by saying him and his brother could come, that way it would be more casual. Although i do not mind messaging first im in the mind set that i am annoying him if i text him, the other thing is that he mentioned on our date that he hates when people don't get to the point and talks around the subject, does that mean he doesnt like casual chit chat through text? Any advice would be greatly appreciated!

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