I would want some signs to look for between enabling a loved-one and caring/being supportive of that person? Is there usually a clear line?”

Well, caring describes a feeling of concern or compassion. Support is an expression of that caring in some positive way. Enabling is about protecting somebody from consequences that might motivate change. You can identify enabling by asking yourself a few simple questions:

  1. What’s the problem behavior, and why is it a problem? For instance: “Ben drops a few hundred bucks every weekend at the casino. He doesn’t make enough to support this habit. Last month he couldn’t pay his rent.”
  2. Is somebody protecting him or her from the consequences of the behavior? As in: “My mother gives Ben money so he can make up his losses. The next weekend Ben is back losing at the tables again.”
  3. Does that interfere with his/her motivation for positive change? “Heck yes. Why should Ben stop gambling when my mother keeps bailing him out of financial trouble?”

Where real support is the result of caring, enabling usually springs from guilt, fear, or a misplaced sense of responsibility for someone else.