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Yeah I'd say he digs you, I've been that guy before, his actions sound par for the course.
And on the chance that he isn't in to you, his lines about the where the road you are going in your relationship with him and on in respect to others in your romantic life, aren't that off base. Either way sounds like he probably has some intimacy issues; I know I'd be a little sore if I felt I was losing a friend more and more day by day, and ultimately there wasn't much that could remedy the situation.
But yeah. Being a gambling man, I'd bet the farm he digs you, but he is that "nice guy".
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To win a war you must serve no master but your ambition.
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