15 questions about
looking back, looking forward
Pick one and start there. You don't have to go in order.
- 1
"What's the most important thing that has happened in your life so far?"
- 2
"What period of your life are you most grateful for?"
- 3
"What's something about your past that makes you who you are today?"
- 4
"What's something you'd tell your past self that you know now?"
- 5
"What has the last five years taught you?"
- 6
"What do you want the next five years to feel like?"
- 7
"What are you leaving behind as you move forward?"
- 8
"What are you carrying with you into the future?"
- 9
"What's something about who you are now that you couldn't have predicted?"
- 10
"What's a version of your life that existed and then didn't — that you're still making peace with?"
- 11
"What does the future feel like to you — open or daunting?"
- 12
"What do you want to be true of your life when you look back at sixty?"
- 13
"What's something you hope you'll have figured out in ten years?"
- 14
"What does 'a life well lived' mean to you today?"
- 15
"What do you want us to look back on and be proud of?"
How to use these
conversation starters
Over dinner
Pick one question at the start of the meal. Let the conversation lead where it wants.
On a long drive
No eye contact makes some questions easier. Road trips are perfect for depth.
Before sleep
One question each before the lights go out. This becomes a ritual you'll both love.
On a walk
Walking side by side reduces pressure. The movement helps the conversation flow.
Sunday morning
Slow morning, no agenda. Phones down. One question over coffee.
In the app
Log your answers in Relationship App: Love Story. Look back on them together.
Keep the conversation
going every day.
Daily prompts, mood check-ins, love notes, and a shared memory of every conversation you have together.