You know that one trip? The one that lives rent-free in your memory? Maybe it was absolute perfection (chef’s kiss), or maybe it was a total disaster—but in a way that makes for an excellent story now.

So next time you’re on a road trip, sitting around the dinner table, or killing time in an airport (because let’s be real, you can only browse the same overpriced snacks so many times), throw this question out there:

✨ “What’s a trip you’ll never forget—and what made it so special?”

It’s an easy question, but the answers? Always interesting. You might hear about someone’s best vacation ever, their weirdest travel encounter, or the time they got stranded in a random city with nothing but a granola bar and questionable life choices.

If you get a blank stare, help ‘em out:

What’s the wildest thing that’s ever happened to you while traveling?

Have you ever met someone on a trip that you still think about?

If you could relive one travel moment, which would it be?

Try it out and see where the conversation goes. You never know—you might just uncover a legendary story… or at the very least, some epic travel fails.

Now spill: What’s a trip you’ll never forget? (And do you still have the embarrassing vacation photos to prove it?)


Jessica Reinhart