Praying specifically: The Fourth Dimension

To be honest I was instantly weary of this guy and his book. The title itself made me cringe (although it's not as weird as it sounds), but for $4 it made sense to at least read it. It's not a very long book and it's full of good info. I was surprised at his Bible knowledge and knowledge of philosophy and anthropology. Anyways...
The guy prays specifically and he challenges his readers to pray specifically. Right away I was thinking "health and wealth gospel." Upon further reading I don't think this is what he's teaching. It really got me thinking.
I don't pray very specifically. I generally pray about something and then ask God to do His thing. I pray mostly for other people and for general things like the church, the community, etc.
So I decided to pray specifically that Silas will be home, in Cowden with us, on Easter. Mindy (my wife) has joined me and so have a few other people. Specific prayer makes me scared. I wonder if it will make me look stupid, or worse, give someone the impression that God is incapable of helping me or doesn't care to help me.
But isn't hope supposed to be expectant? Aren't we supposed to pray actually believing that the prayer matters and that the prayer is important and life changing? Do I, as a Christian, really believe that prayer works in real life and not just on some existential plane? Am I tempted to pray generally because I don't really believe that God cares about what I care about? Do I believe that God is far-off or near?
Do I pray generally because I don't want God to look bad? Am I trying to give myself a way out?
I believe He is near and I believe He has heard my prayer for Silas to be here by Easter.
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