Excerpt from my latest Sasstrology article (please leave comments on the Sasstrology site):
"Chiron/planet contacts are some of the most complicated in synastry. Chiron’s association with pain and healing adds poignancy to a relationship; there’s a sense of great possibility, combined with the threat of being hurt. And someone will get hurt. Chiron is based on a wound, and if another person’s planet activates it, some pain is inevitable. But Chiron contacts don’t work in the same manner as other interaspects, meaning who feels what is not straightforward. Much depends on how the Chiron person is dealing with their wounds, and how the planet person deals with vulnerability."