Resuscitating this thread...Experiencing this now with someone. My Mercury in Aries squaring his Chiron in Cancer, which is conjunct my ASC in Cancer. (My South Node in Cancer is nearby - and get this, his South Node in Leo is close to my Chiron in Leo, giving us DW Chiron-SN albeit with wide orbs.)
Anyway I am trying not to trigger him. He brings out my compassion, he seems completely vulnerable and lacking confidence around me. Basically very intimidated by me when we talk. I worry about my Aries Mercury all the time because I know I can be very thoughtless and brutal with my words even when I think I'm toning it down lol
In any case he seems extremely vulnerable when we talk and the few insights I've given seem to have made an impact. For example, I told him a habit of his was a sign of perfectionism and he looked at me like I had just stabbed him lol! But in a "how the F did you know that" way. And when I've shown him compassion he seems to have been extremely touched. He has natal Jupiter on his Chiron too, so my ASC is hitting them both.
Oh, and there are definitely themes of mentoring - him mentoring me with creativity (my Chiron in Leo). He does it spontaneously, without me asking, though I really appreciate his help.