Our expert says:
I suspect many people didn't specifically learn this, but just naturally had a bit more self-esteem and self-confidence, and didn't expect to fail ( and when they did fail in approaching someone else, as everybody does at times ) So they tried, they weren't devastated when it didn't work, and just enjoyed it when it did. Sometimes thinking too hard about such things can actually make it a bit more difficult.
Yes, some self-help books are so much less helpful than you need - they're a bit like reading a car on safe driving that just says " Dont have acidents".
Counselling, especially of the CBT type ( Cognitive-Behaviour Therapy ) can help significantly, to boost your self-confidence, discuss people skills, and let you take more effective control over the process.
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