Ask Amy: High-maintenance friend is a drama-drain

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. The problem then becomes that she thinks she is in a relationship with them, and is then crushed when things don’t work out. And they never work out. I’m not exaggerating.


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

Charlene has behaved this way since the day we met.


She 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. It completely drains me.

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

She wants me to drink with her, but I won’t, because she has a problem.

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.

It’s exhausting but I feel guilty and terrible for feeling this way.

Am I a bad friend?

– Bad Friend


Dear Bad Friend: 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 non-judgmental place to fall, she doesn’t need to face the underlying source of her drama.

Try some non-judgmental 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: My family and I live in my mother-in-law’s house. It works out well for all. I have a concern about my mother-in-law, however.

She writes a check to pretty much any charity that asks. She doesn’t give large amounts – just $10 or $20, for the most part. 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.

Giving to charity is not the problem. I believe 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 – that for every $10 she sends, maybe $1 or $2 make it to someone in need.

We suggest that she choose one or two causes that are very dear to her and give only to them, even in much larger amounts that might equal what she gives to all of these various organizations, added together.

What do you think? 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?

– Worried

Dear Worried: 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 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 and, as you do – look up the organization to learn more about them, and show her the results.

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

I urge all of you to keep your giving local! Your local animal shelter, cultural institutions, library, and children’s after-school programs would all appreciate a boost. Your mother-in-law’s donation would go much farther, and she would have a personal connection to the institution receiving it.

Dear Amy: Thank you for your reply to “Casual?” who was dating a dad, but didn’t enjoy spending time with the man’s son.

I was so glad that you stood up for this boy. A child should always be the parent’s priority, and anyone dating a parent should understand this.


– Single Parent

Dear Single Parent: I appreciated “Casual’s” honesty regarding this situation.

©2022 Amy Dickinson.