Ask Amy: An Adventurous Trip with Grandma?

Dear Amy: I’m very active and adventurous. I started an annual tradition with my daughter to take her on mommy-daughter adventures for her birthday (like hiking, kayaking, horseback riding, etc.).

We’ve done this for six years now and it’s been incredibly special.

This year I decided to splurge on a Maui trip (vaccine dependent, of course).

The complication is that my mom kind of invited herself along. She’s pretty overbearing and can be quite unpleasant to be around, but I know she’s feeling sad and lonely since losing her husband two years ago. She is not adventurous, nor in good physical health. Walking a mile would be difficult for her.

I told her that I was planning a lot of things she might not be able to do. She said that was fine.

I said I could take care of the lodging, but she would need to buy her own plane ticket. Now I am regretting this.

I really try to stay out of hotels. She yelled at me that she, “needs a pool, so we have to stay at a hotel.”

I found a condo that was right on the beach. She got angry and yelled at me that maybe she shouldn’t go.

I fear this is the start of many more issues and will result in a miserable vacation. I honestly am tempted to tell her to stay home.

She has not bought her plane ticket yet. However, this will cause a huge problem in our relationship. What should I do?

— Good Mom, Bad Daughter

Dear Daughter: Because your mother is both discerning and overbearing, the best way to manage this three-generation trip from heck might be to simply make whatever lodging choice you want to make, offering the safest and most accessible accommodations for all three of you, and if your mother doesn’t like it, she can choose to stay behind. She has already threatened to stay home, and if she can’t control your choices, that might be her preference.

It’s possible that she merely wanted to be included in the first place, and that she has been testing you.

I’d like to make a pitch for you to consider experiencing a change-of-heart, however.

There is a likelihood that you and your daughter will have many mother-daughter adventure holidays ahead of you. But the biggest and riskiest adventure you two might ever take could be the one you face right now: Traveling with your cantankerous and challenging mother. I wonder if you are brave enough to take that on.

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In the tradition of the great personal advice columnists, Chicago Tribune’s Amy Dickinson is a plainspoken straight shooter who relates to readers of all ages. She answers personal questions by addressing issues from both her head and her heart. A solid reporter, Dickinson researches her topics to provide readers with informed opinions and answers. Ask Amy, P.O. Box 194, Freeville, NY 13068

© 2021 by Amy Dickinson