Sentence:  I've thrown away my reputation, self-respect, money, health and happiness through the use of drugs and alcohol; I can teach her how fragile a reputation is, how a fool and their money are soon parted, and how dangerous it is to <WSD>flirt</WSD> with drugs. 
Meaning of the word marked with <WSD> tags:  To experiment, or tentatively engage, "with"; to become involved in passing "with".