Today’s divisive political climate has made the idea of talking to those on the “other side” an act of traitorous betrayal. At the same time, psychoanalysis has a long history of attempting to bridge what can feel like irreconcilable differences and splits as they appear in both individual and group dynamics. Rather than following the expectable, and often appropriate, tendency to avoid conversations that break down into attacks and opposition, I will explore what is possible when we are willing to place ourselves intentionally in the line of fire between polarized groups. I have found that the type of dialogue that can evolve using a “group relations” approach can be particularly useful in working through conflict to arrive at a fuller and more honest understanding of self and politics.