Dear Amy: My friend and co-worker has a teenage son (age 15) who has been in trouble for most of his life. This has gotten worse the older he gets.

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

She does not seem to understand the severity of his actions, nor the recourse for them. She is also extremely hardheaded 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?

Amy says: If you have personal or professional experience dealing with an extremely challenging teenager, then you should weigh in (when invited) supportively and share all the 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 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 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 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.

Awkward holiday

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 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.

I know it would be easier NOT to participate in a Zoom, but maintaining my relationship with Mom's family is important to me.

Amy says: 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.

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 maintaining your own connections.

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