If we have a Police chief advising students "to focus on being empathetic and [build] relationships with the homeless population", that's a whole other issue! We certainly don't need students interacting with a group connected to a high level of crime and other nefarious activities. They could work behind the scenes with professional organizations trained to assist this population in transitioning out of homelessness, volunteer at food banks, etc., but there is no way we want to encourage teenagers to personally interact and build relationships, which may well turn into themselves becoming victimized!
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