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It's a little different for me as a collegiate, but I've had some success by reminding them of the ridiculous stereotypes of a group they're in, and that accepting them without seeing for themselves first is letting someone else think for them. Like an "Oh right, because all of the marching band kids are completely socially inept? If you start to think for yourself and want to make your own decisions, I think you'll be really surprised when you actually go talk to sorority women."
The upperclassmen who convinced me to go greek (I was very much the resistant freshman girl, as it goes) tried the normal routes, and then finally went "Just come out and meet some of the girls! Just stop accepting what others tell you and give it a chance. Then you can decide for yourself that we're all dumb and useless."
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heartsunshine
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