Jesus spent his days with the outsiders and outcasts of society, so this is a good illustration of how that may look if translated to our contemporary society. (Although not necessarily wearing high heeled shoes.)
He chose to be with prostitutes, money collectors and fishermen, and told stories of good Samaritans… all looked down at or shunned by his community. Who would he choose friends among today? Maybe the homeless, insane, industry workers, truckers, Muslims, turban wearers, gay, transsexuals, hiv positive… not to change them or convert them, but to find friends in them, and show the rest of us our prejudices.