Life Advice



Ask Amy: Troubled son keeps coming back for more

Amy Dickinson, Tribune Content Agency on

Dear Amy: My son has been in trouble with the law for the majority of his life. I have never turned my back on him and at one point even paid an attorney $20,000 to keep him from spending his life in jail.

This was a one-shot deal, and I told him that at the time.

About a month ago, he reached out to me to pay for his latest mess. I refused, telling him I was done helping him financially and he needed to solve it himself.

He has a great job that pays well.

His response was quick and vicious. I continue to be hurt and stunned by his remarks.

He ended the conversation by telling me not to show up at a planned family function, and then he hung up on me.

We haven’t spoken since.

I am so disappointed in him; primarily that he is still breaking the law and secondly for being an ungrateful brat.

I am tempted to remove him from my will and just move on – but this is my child.

I don’t know what to do.

Any suggestions?

– Sad Mom

Dear Sad: Your son does not seem to have adequate control over his own life – do not let him control yours.

You are not a criminal. You’ve done nothing wrong. Your son’s vicious statements and behavior are the actions of someone who feels entitled and is willing to be ruthlessly manipulative to get what he wants.

You saved his bacon once; now it’s his turn to take full responsibility for consequences flowing from his own choices.

If removing him from your will helps you to feel in control of your role in his life, then – do that.

Yes, he does sound like an ungrateful brat, but you should not expect gratitude unless or until he bottoms out, runs out of options, and faces an actual and proportional reckoning.

He will always be your son. You don’t need to like him, but I hope you will be able to continue to love him – even from a distance.

Unless a family function is being held at your son’s home, then he doesn’t get to tell you to stay away. Otherwise, you should go wherever you want to go, regardless of the relationship.

Dear Amy: I'm a 70-something mother of two adult sons and an adult daughter. I have health issues. My will was set up with each of my three kids getting one-third of my estate.

Over time I began to question leaving anything to my two sons who live far away and NEVER call to see how I am, which hurts me.


Recently my grandson (age 16) made a perfectly rational decision that his father, my eldest son, disagreed with.

My son responded by telling my grandson that he could not live with him anymore.

This child was then forced to have to leave school and all his friends in his senior year to move hours away to live with his mother.

He went from being a happy and gifted student to being an academically troubled, depressed young man.

I let my son know that I disagreed with his decision, and he stopped talking to me. He has since ignored all communication.

Would I be wrong to cut him out of my will and to give his share to my grandson, instead?

– Troubled Mom and Grandma

Dear Troubled: You should make whatever choices you want to make regarding your will.

I do suggest that you might want to use some assets before your death (if possible) to support your grandson’s growth and positive choices regarding his own future.

If you can afford to, you might consider offering to pay his first semester’s tuition at his local community college.

This offer of a gift from you might inspire your teenage grandson to press on with his education, as well as demonstrate your faith in his future.

Community colleges are a great and affordable bridge for students to continue their education, and have helped many young people to kick-start their passion for learning.

Dear Amy: Thank you for standing up for restaurant servers, who have an extremely tough job these days.

I am a server. I worked while wearing a mask when customers chose not to, I worked extra hours when other staff were sick or quit, I have absolutely done my best under extremely challenging circumstances, and I live off of my tips.

– Grateful

Dear Grateful: I hope your employers and customers show their gratitude to you.


(You can email Amy Dickinson at or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)

©2022 Amy Dickinson. Distributed by Tribune Content Agency, LLC.




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