15 questions about
success & failure
Pick one and start there. You don't have to go in order.
- 1
"How do you define success — honestly, not performatively?"
- 2
"What's a failure that turned out to be important?"
- 3
"Do you feel successful right now?"
- 4
"What's something others consider a success for you that doesn't feel like one?"
- 5
"What's something you consider a success that no one else knows about?"
- 6
"What's the most important thing you've ever failed at?"
- 7
"How do you handle failure — what happens in you?"
- 8
"What's a failure you haven't forgiven yourself for yet?"
- 9
"What does 'enough' look like in terms of success?"
- 10
"What's the best failure you've ever had?"
- 11
"How much does external recognition matter to you?"
- 12
"Do you compare yourself to others — and how does it affect you?"
- 13
"What would you do if you knew you couldn't fail?"
- 14
"What's a success that cost more than it was worth?"
- 15
"What does living a meaningful life mean to you?"
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.