30 Days of Deep Conversation Ideas for September to Discuss With Loved Ones

If you’re excited to get to know someone on a deeper level, or want more meaningful conversations with friends and family, try our 30 days of deep conversation this September.

There are plenty of great ideas here to discuss. Chat about one a day for the whole month, or pick and choose the ideas you’d like to talk about. You can get the full calendar as a printable at the bottom of this post.

Something you’re looking forward to this fall.

Your favorite memory from past fall seasons.

One thing you’d change about the past.

One thing you’d change about the present.

What fall tradition you’d like to start.

Your first significant fall memory.

Something that’s on your fall bucket list.

If you could go ‘back to school,’ what you’d study.

Something you want to accomplish by the end of the year.

How you feel this year has been so far.

The most important thing that happened this year so far.

Something you wish you’d learned sooner.

If you had to relive one year of school, which one you’d pick.

Your favorite rainy day movie.

The song you play on repeat and why.

The biggest challenge you’ve overcome this year.

Three things you’d change about this year.

Where you see yourself in five years.

Where you see yourself in a decade.

Something that would surprise people to know about you.

A dream you have that most people wouldn’t guess.

What the meaning of a ‘good life’ is to you.

Someone who inspires you deeply and why.

A time you felt like you made a difference.

Your top three desert island items.

An opportunity you wish you’d taken.

If you could do anything for a day, what it’d be.

A memorable surprise and what made it special.

What song you’d pick as the soundtrack to your life.

If this September was a book, what you would title it.

Get the September Deep Conversation PDF Printable here.

Check out more conversation starters for additional ideas here.