Beyond small talk: 16 deeper questions

A minute or two of chitchat is normal. The conversations that stick with you, though, are the ones that got honest. None of these have a right answer, and they land better after the two of you have already shared a laugh.

Name a belief you held for years and later dropped.
What's the best advice you've ever ignored, and was it a mistake?
What does a really good regular Tuesday look like for you?
Which quiet win are you proud of but rarely mention?
What would you tell yourself at 16?
What's a fear you had that turned out to be nothing?
Who's the person who shaped you the most?
What's a question you wish people asked you more?
What's a choice you almost didn't make that changed everything?
Where do you feel most at home?
What would you try if you knew you couldn't fail?
What's the nicest thing a stranger has ever done for you?
What's an opinion you hold that most of your friends don't?
Which small habit has helped you more than you expected?
In what moments do you feel the most you?
What are you trying to figure out right now?

Ready to use these? momos matches adults for free 1-on-1 video calls, and every call has prompt cards built in.

Start a video chat

Good moments to ask

Once the call has loosened up a bit.
When things are flowing and you'd like to go a level deeper.
With someone you friended after a previous call.

Mistakes to skip

Leading with one. It's heavy coming from someone you met ten seconds ago.
Pressing if they sidestep. Let it go and switch topics.
Answering their story with a more dramatic one. Meet them where they are.