1) Caused distress to 2) Caused travail 3) Displeased 4) Distressed 5) Expressing anguish 6) Grimacing 7) How it hurt dad to upset Enid 8) Hurt 9) Hurt or upset 10) In agony 11) In distress 12) Kind of expression 13) Like a wince 14) Offended 15) Showing anguish 16) Showing discomfort 17) Showing irritation Found on https://www.crosswordclues.com/clue/pained