Sounds like he digs you but has intimacy problems. If I were in his shoes and had been doing the nice things he's doing, I would have made my move by now. Speaking as a guy, everything you say about him telegraphs affection. Maybe he's been burned in the past and can't quite get the wagon back on the trail yet. But he's had a helluva window of opportunity and hasn't done anything with it. I think he's holding himself up to a pretty high standard, so much so that I wonder if their isn't some relationship sin in his past that he's trying to absolve himself of.
Either way, his actions don't match his words. He's involved in your life pretty heavily, yet he insists you should make your own decisions. He insists he's not romantically interested, yet the feedback he gives you when you tell him about your dating life says the opposite to me. He sounds like a great guy who's killing himself a little bit each day because he doesn't have the courage to make the leap. And I'm willing to bet there's a little world-weary cynicism that has him convinced he'll be rejected.
But I ain't gonna offer you any advice, sister, and you've probably already come to similar conclusions anyway. If he doesn't go for it, he has no one to blame but himself. I can only have so much sympathy for a guy who's apparently intent on not helping himself out.
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"The idea that money doesn't buy you happiness is a lie put about by the rich, to stop the poor from killing them." -- Michael Caine
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