This study examined how message characteristics and relational turbulence correspond with victim and perpetrator experiences of hurtful messages. Romantic partners described 2 events: one where each of them was a victim of the partner's hurtful message. Trained judges evaluated qualities of hurtful messages and participants reported relationship qualities, intensity of hurt experienced as a victim, and the partner's hurt feelings when the respondent was the perpetrator. Third‐party ratings of hurtfulness were associated with victims' intensity of hurt. For females, relational turbulence was associated with their intensity of hurt as victims. For males, relational turbulence was associated with their perception of the female victims' hurt. The authors discuss the implications for the work on hurtful messages and relational turbulence.