15 questions about
work & career
Pick one and start there. You don't have to go in order.
- 1
"What does professional success mean to you, specifically?"
- 2
"Is there something you've always wanted to do professionally but never pursued?"
- 3
"Do you feel like your work reflects who you are?"
- 4
"What would you do for work if the salary were the same for everything?"
- 5
"What sacrifices have you made for your career — and were they worth it?"
- 6
"How important is ambition to you, and has that changed?"
- 7
"What's something you're quietly proud of that your work doesn't reflect yet?"
- 8
"If you could start your career again from scratch, what would you do differently?"
- 9
"What does the ideal workday feel like?"
- 10
"How much does being respected in your field matter to you?"
- 11
"What's something about work you find unexpectedly meaningful?"
- 12
"What's the most important thing work gives you beyond money?"
- 13
"What does enough look like in terms of professional achievement?"
- 14
"How does work affect your sense of self-worth?"
- 15
"What would your career look like in five years if you were brave enough?"
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.