I think that's when you moon someone but keep your pantyhose pulled up for modesty's sake. But, I might need clarification on that point.
I think of St. Catherine of Siena when I see this phrase. I think it means being willing to stand up for orthodoxy without giving a fig about what other people think or say. Or, maybe caring but finding oneself more worried over what God thinks regardless.
The group of overly pious and devotional people I'm chummy with from Church issues the "Holy Boldness Award" weekly to the most deserving among us. Past recipiants have been awarded the title for such pious actions as encouraging a priestly vocation in a young man more intent on picking up the ladies, accosting a female usher at church for her statement that she "hates Latin and the Pope," and asking a protestant pal "So...when are you going to join the REAL chuch?"
No way of knowing what your estranged source meant by it, but at the risk of giving a straight answer, holy boldness is the audacity to step out in faith to be a witness for God, usually at the prompting by and help of the Holy Spirit. :D
Sorry, can't think of an answer for you, but if you find a good one, please let me know!
The first image that comes to my mind is St. Stephen at his trial, giving witness in a manner he had to know would lead to his death but which needed to be said at that time and that place. We don't encourage that kind of boldness because most people don't know how or when to do it; as a result, times when such zeal is called tend to slide by without response.
Any phrase prefixed with holy is positive in my mind. Boldness by itself may be motivated by selfish reasons. But holy boldness is being courageous for the sake of the ultimate Other.
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