9 Questions To Ask About Someone’s Big, Life-Changing Trip.

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Every Wednesday is Tip Day. This Wednesday: 9 questions to ask about someone’s big, life-changing trip.

One of my resolutions is to Enter into the interests of other people’s lives. When you think of people getting along harmoniously – whether in a family, or among friends, or in an office – people make an effort to enter into the interests of each other’s lives.

My friend Michael Melcher (author of the terrific book The Creative Lawyer — which isn’t just for lawyers) pointed out to me an area where this is often an issue: with travels. It’s quite common for people to come back from big, life-changing trips, and feel let down because no one seems very interested in what they saw or thought or experienced.

Part of being a good friend, colleague, or family member is to show an interest, but this can be challenging. Often, people need help finding ways to talk about their travels in ways that are interesting to people who weren’t there.

I’m not much of a traveler, myself, but Michael is, and he suggested nine questions that you might ask, to enter into the interests of a newly returned traveler. The point, of course, is not to fake an interest, but rather to find a way to be sincerely interested.

9 Questions to Ask About Someone’s Trip

1. What was the best moment of the entire trip?

2. What are two interesting things about China [or wherever] that the average person doesn’t know?

3. Tell me about one person you met.

4. Now that you’ve been there yourself, when you think of China, what’s the first image that comes into your head?

5. What was the hardest or most frustrating part of the trip?

6. Did anything go wrong that seems funny now? [I often remind myself of my Secret of Adulthood that “The things that go wrong often make the best memories.”]

7. What little, ordinary thing did you miss from your usual routine?

8. What did you learn about yourself?

9. Now that you’ve been to China, what are two other places you’d like to go?

What am I missing? Have you identified any questions that are good at invoking interesting conversation? And travelers, when you come home, what questions are interesting to answer, and that show interest in what you’ve experienced? Have you ever been frustrated by the fact that people don’t seem interested in hearing about a trip or adventure that was very significant to you? Because I’m not much of a traveler, myself, I know that I haven’t shown as much interest in people’s travels as I should have. Something to work on.


From 2006 through 2014, as she wrote The Happiness Project and Happier at Home, Gretchen chronicled her thoughts, observations, and discoveries on The Happiness Project Blog.

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