How close of friends should a guy be with a girl to rest his head on her boobs?

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This is a question you ask of the girl (note: call them men and women, not guys and girls) and not of the relationship. There is no ‘magic’ relationship status that any guy can achieve with any woman that would allow him unfettered access to using his friend’s bosom as a pillow.

Best give the question verbal affirmation before taking any hasty steps. “Say young lady, your lovely bosoms look perfect for usage as a fine soft pillow! Surely you wouldn’t have much objection to me resting my impossibly manly head on them! Please please pretty please???”