Ask Amy: Friend wants to weigh in on troubled teen

Dear Amy: My friend and co-worker has a teenage son (age 15) who has unfortunately been in trouble for most of his life. This has gotten worse the older he gets. (I am not talking about small incidents either. There has been racism, violence, and other problems that are serious.)

He has been disciplined several times already at school, and now is currently attending the “alternative” school and has been kicked off both band and athletics, in which he excelled.

She seems to have rose-colored glasses on and does not seem to understand the severity of his actions, nor the recourse for them. She is also extremely hard-headed and must always be right (*sigh*).

She has asked my opinion several times and I have generally deferred, knowing it will upset her. Should I tell her what I think, or simply let it go? I confess it is hard to watch because no good can come from the path he is currently traveling down.

Your advice would be greatly appreciated.

— A Friend

Dear A: If you have personal or professional experience dealing with an extremely challenging teenager, then you should weigh in (when invited) supportively and share every ounce of expertise and commiseration you can.

In short, can you actually help her? If so, you should.

Merely stating your opinion about how badly her son is messing up (or highlighting the severity of his offenses so she’ll pay closer attention) might make you feel righteous — and right — but wouldn’t offer a pathway toward change.

The way you present your friend’s personality, I could imagine that there are ways her own temperament might have contributed to her son’s behavior. Again, offering an indictment of her personality or parenting style isn’t likely to inspire change.

If you lack expertise and experience, you might gain traction by asking questions: Has she been offered professional help? Has he? Has she been following professional recommendations?

Listen to her answers with compassion, and if she asks you what she should do, say, “Every child is different. I can’t really say what YOU should do, but I can tell you what I would try to do.” If she responds defensively, you’ll know that she isn’t ready or able to listen.

There is no one answer in how to parent a troubled child. It is a very long and lonely road. Be extremely judicious in doling out advice, while offering support in abundance.

Dear Amy: My mother passed away earlier this year.

Shortly afterward, my father started seeing someone. She has basically moved in with him.

Before I knew about his new romantic partner, my wife and I were planning to have Christmas dinner at his home since they are part of our small quarantine bubble of four.

We were also planning on doing a Zoom dinner with my mom's side of the family.

They have no clue about this relationship, and I imagine there's going to be a lot of awkwardness if we do this. What do you think I should do to reduce this awkwardness?

My wife thinks I should ask my father to try to be more transparent. He hasn't given me many details about his new partner, and she is not very talkative, so I don't know much about her. I don't even know her last name.

I know it would be easier NOT to participate in a Zoom, but maintaining my relationship with Mom’s family is extra important to me now that she is no longer with us.

— Feeling Awkward

Dear Awkward: Please accept my condolences. The entire holiday season will likely be quite tough for you this year – for many reasons. I can understand why you are anxious about this particular episode.

You don’t say whether your father wants to do a Zoom gathering from his house. Please remember, as you worry about this, that it is up to HIM to manage introducing his new partner to other people, and that includes managing the awkwardness. You should try to detach from your own expectations about how he will handle this and focus on your own connection to these family members.

Dear Amy: “About to Blow” didn’t like to be asked how much money they paid for things.

My mother always said, “There are three things I do not discuss: My age; my weight; and my money – in that order.”

That shut up nosy people pretty quickly.

Hope this helps. She lived to 99-1/2.

— Smart Mom

Dear Smart: I may be borrowing her wisdom.

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