Fetching details from the dictionary...
smiling with pity
彼の浅はかな言動に憫笑を禁じ得なかった。
I could not help but smile with pity at his shallow behavior.
世間知らずの発言に聴衆は憫笑した。
The audience smiled pityingly at the naive remark.
憫笑を浮かべながらも助言の手を差し伸べた。
While smiling with pity, they extended a helping hand of advice.