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Don't tell your friend that she can't date him, just let her know that he is pretty sketchy and has hurt women in the past.
Have words with the guy. Explain that you would rather he leave her alone, and the should he choose to date her anyway, you will hold him personally responsible in the event that he hurts her.
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"Socialism is a philosophy of failure, the creed of ignorance, and the gospel of envy, its inherent virtue is the equal sharing of misery." - Winston Churchill
"All men dream: but not equally. Those who dream by night in the dusty recesses of their minds wake in the day to find that it was vanity: but the dreamers of the day are dangerous men, for they may act out their dream with open eyes, to make it possible." Seven Pillars of Wisdom, T.E. Lawrence
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