When a man flirts with a woman, and he unintentionally harms her in any way in the act of trying to bond with her. His friends describe him/his actions with the statement: when he flirts, he hurts.
1: Dude, do you know that kid Kyle?
2: Yeah, he was flirting with that chick last night.
1: Did you see what he was doing though?
2: Yeah, when he flirts, he hurts...