50 Deep Questions to Ask on Long Fall Walks

There is a specific quality to walking side by side with someone that is different from sitting across from them.

No eye contact to manage.

Your hands occupied or swinging freely at your sides.

The rhythm of moving together at the same pace, the same direction, through the same air.

I think this is why some of the most honest conversations I have ever had happened on walks rather than over meals or in rooms.

Something about moving your body loosens something in your brain, and the absence of direct eye contact removes the pressure that makes certain things hard to say while looking someone in the face.

Autumn makes this even better.

There is something about fallen leaves and cold air and the particular golden-grey light of an October or November afternoon that already feels contemplative before you have said a word.

The walks I have taken with people I love in autumn are some of my clearest, warmest memories.

Not because anything dramatic happened on them.

Because something about that specific combination — movement, cold air, changing season, nowhere to be — made the conversation go somewhere it might not have gone anywhere else.

These fifty questions are organized from lighter to more honest.

There is no right order.

Skip the ones that don’t land.

Come back to the ones where one of you goes quiet for a second before answering.

Those are usually the good ones.