Ask Amy: Vulnerable friend needs to hear the truth

Dear Amy: I love my friend "Charlene," but she is the very definition of high-maintenance.

She drinks way too much — every day — and sleeps with strangers she meets in bars. She thinks she is in a relationship with them, and is then crushed when things don't work out. And they never work out.

She is very vulnerable. She is desperate for an authentic and loving relationship, but men have used, abused and taken advantage of her.

Charlene ignores every piece of advice I give her, but then she expects me to be a shoulder to cry on when her life falls apart.

I try to be supportive and nonjudgmental because she really is a beautiful person. She has been there for me through some tough times, but this friendship has become draining.

She is in counseling but constantly uses me to vent and cry to. I love her dearly, but I don't want to be that listening ear anymore. I feel guilty and terrible for feeling this way. Am I a bad friend?

Amy says: The only "bad" thing you've done is to possibly delay Charlene's recovery by offering advice but not giving her the unvarnished truth.

Understand that as long as she has you as her soft and nonjudgmental place to fall, she doesn't need to face the underlying source of her drama.

Try some nonjudgmental honesty: "I'm exhausted by this drama. I've tried to help you, but I've failed. At this point, I just hope that when you're ready to change, you will."

Dear Amy: I have a concern about my mother-in-law.

She writes a check to pretty much any charity that asks. She doesn't give large amounts — just $10 or $20. But, of course, those same charities send a never-ending barrage of mail, and now, seemingly every other charity in the country has been sold her address and sends her solicitations.

Furthermore, I believe that many of these charities are not using her money wisely, or are completely random charities in far-flung places that have nothing to do with the many causes that might actually affect her life.

We tell her that, in some (not all!) cases, she's just throwing money away. We suggest that she choose one or two causes that are dear to her and give only to them, perhaps in much larger amounts that might equal what she gives to all of these various organizations, added together.

I've tried to look up some of these places on charity watchdog websites, but most don't even show up on them (which should maybe tell us something)! Any advice?

Amy says: Some "charities" (and I use that term loosely) seem to exist mainly to hook generous and concerned older people into the cycle you describe.

I use Charitynavigator.org to look into any nonprofit I'm interested in. This organization uses many different metrics to assess a charity, and its rating system has a reliable reputation.

I hope you will continue to keep a close eye on your mother-in-law's giving. Go over these solicitations with her. Look up the organizations to learn more about them, and show her the results.

She has the right to do whatever she chooses with her money, but she might be the victim of exploitation — or a scam.

I urge everyone to keep your giving local. Your local animal shelter, cultural institutions, library and children's after-school programs all would appreciate a boost. Your mother-in-law would have a personal connection to the institutions receiving her donations.

Send questions to Amy Dickinson at askamy@amydickinson.com.