15 questions about
hardest times
Pick one and start there. You don't have to go in order.
- 1
"What's been the hardest period of your life?"
- 2
"What got you through?"
- 3
"What did the hardest time teach you?"
- 4
"Is there a difficult period you're still processing?"
- 5
"What do you wish you'd had during your hardest time?"
- 6
"How did a hard time change you?"
- 7
"What strength did you discover in difficulty?"
- 8
"What support from me has meant the most during a hard time?"
- 9
"What do you wish I'd done differently when you were struggling?"
- 10
"What does resilience mean to you?"
- 11
"Is there a hard time in your past that I don't fully understand?"
- 12
"What do you know about suffering that you wish you didn't?"
- 13
"What's been the hardest thing about loving someone else?"
- 14
"What's a chapter of your life you're grateful is behind you?"
- 15
"What's something hard you're carrying right now?"
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.