15 questions about
fears & insecurities
Pick one and start there. You don't have to go in order.
- 1
"What's a fear you've never fully admitted to anyone?"
- 2
"What are you most insecure about — and where do you think that comes from?"
- 3
"What's something you're afraid will never happen for you?"
- 4
"What do you worry about most at 3am?"
- 5
"Is there a version of failure you're terrified of?"
- 6
"What's something about yourself you're still trying to accept?"
- 7
"What kind of rejection do you find hardest to handle?"
- 8
"What do you fear most about the future?"
- 9
"Is there something you pretend not to care about that you actually care about deeply?"
- 10
"What are you afraid people see when they look at you?"
- 11
"What do you wish you were braver about?"
- 12
"What's a fear that has held you back from something you actually wanted?"
- 13
"Is there something about getting older that genuinely frightens you?"
- 14
"What would you do if you weren't afraid?"
- 15
"What's your biggest fear about our relationship?"
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.