I personally feel giving should be done out of a spirit of generosity and generosity should be part of one's path. If one lives from generosity then one will not have such feelings of undeserving when asking. It is natural that we are interdependent, its the untrained mind that creates the painful illusion that we are separate.
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I love that "spirit of generosity", and yes we can't pull ourselves up by our bootstraps unless we have help from other people.