I think it’s an inherent risk we all take. I read part of of a comment below that seemed advisable but I have always seemed to be ok with the risk and listen to my instinct to guide me.

A Taker is going to take. A Giver is going to give. Spend enough time watching someone until you know which of these two natures they have. The more precious things you have the more takers you will be confronted with. Remember that a taker will try to blur the lines. Once people show you who they are believe it. Love yourself enough to respond in your best interest.

You can be compassionate just remember to set and keep boundaries... Don't ignore red flags!

I just consider myself a compassionate fool. I think you just need to be who you are not worry about being played. Compassion for me is internally inspired. I give of myself without accounting, auditing or keeping score. I do it because is right for me.

I only get fooled by people I trust. Therein lies my problem.

I've been there and I've been burned doing so. After which, I get a 'Fuck'em all' attitude for a while. Then reason resumes and I find myself not wanting to let some pathetic asshole change who I am. Ultimately if someone I'm willing to help out screws me over, they've hurt themselves more than me. They lost any support and aid they could have gotten from me in the future, and anyone I know that they can ask for help will be warned.

Basically, I don't want to react to an asshole by becoming one myself. Maybe that would be justified or I could rationalize it, but I still have to live with who I am.

It’s tough. Machiavelli wrote about this a lot. A person that is willing to do evil has more tools at their disposal to achieve their goals. While the good are at a disadvantage.

It's always a risk to trust someone you don't know. It's even a risk when you think you do know them.
Be compassionate, to a point, but don't be a sucker for a sob story.
Healthy skepticism is not a bad thing.

I'd say it's an inherent risk. You can't know what someone is thinking, and sometimes you guess wrong, even when it's someone you actually know.

There's no risk to being compassionate. One just has to have clear boundaries. This is the path I've chosen and it's totally enriching.

Just don't be a friggin' patsy.

Ha, yeah, patterns...

I have learned to not give anyone I work with a gift. They don't appreciate it. I've learned how to say NO to everyone whom asks me for money. Whether it is at home at my residence or at work. My co-workers get more hours and are paid more than me. The answer is an automatic NO. The residents get between $50-100 a month from their Medicaid for spending money, the answer is automatically NO. None of my good friends are that stupid to ask me, they all have higher paying jobs. I once was a fool and got played for lending money. I learned my lesson.

I like to think of what Ram Dass says, "fierce grace." I interpret that as, being tough while remaining tender. Being kind without necessarily being "nice."

It's always a risk. But I think you have to ignore it and do what your gut (heart?) tells you. Overthinking almost never works, in my experience.

Clarify, please?