This reflective autoethnographic essay grapples with how the January 6 insurrection challenged our progressive, White, middle-class, privileged family in our relationships with those who support the insurrection and former president Donald J. Trump in our southern coastal city. Our children navigate new realizations about other White, privileged children who they never realized did not share their values. I struggle with how sensing the difference in another family's values, I still allowed relationships to grow. After our children's friend began arguing about the legitimacy of the election and vocalizing his dislike of our gender creative son's chosen aesthetic, we re-evaluate the safety of the friendship. The January 6 insurrection intensified our children's fear and concern. They collectively became uncomfortable around people they now tangibly understand desire leaders that will target their beliefs, their marginalized friends, and for our gender creative son, his safety. I explore the balance of values, personal protection, consequences, education, hope, growth, and forgiveness through personal narrative.