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I think the reasons against it typically given are that it's degrading to women. The way I've heard of it being done, the girls selected as little sisters were normally the girls who were always around the house late at night, and it was just kind of a way of acknowledging a f***buddy.
And if you put it to him as girls wearing your letters, no he can't care. Let him see a little sisters composite or hear you referring to it as little sisters and I guarantee you he won't have such a shiny outlook on it.
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