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If he is interested in you but could not make the first move then he has a fear of rejection. The only way he deals with that fear is to face it head on. That fear doesn't go away but morphs into fear of intimacy. He is basically insecure and will always hold back (in the relationship) when it comes to opening up to you about unflattering aspects of his personality, life, etc.
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This isn't related to the topic, but I wanted to chime in and disagree with this. Someone being afraid to ask someone out is not enough to infer that they also have a fear of intimacy and will also be afraid to open up to you.
When I was younger I had a fear of rejection but it definitely didn't morph into these other things. I think there are many people that open up very quickly but have a hard time with the initial step.
Several years later I still don't like asking people out, although I will do it. But I've never had the least bit of a problem with intimacy or being very open with my partner about my negative qualities.
I think I always used to be very open with people in my "circle of friends and family", but had problem with strangers or people I was somewhat unfamiliar with. It's still a work in progress changing this.