A good question is the simplest way to say “I’m curious about you”. A bad one turns a chat into a job interview. The difference usually isn’t the question itself but what you do after the answer: listen, add something, share your own.
We’ve grouped these 40 questions into four sets. You don’t have to ask them in order. Pick the ones that fit the pace of the conversation.
Easy openers
For first messages or the first few minutes. Easy to answer, with room for a follow-up.
- Where would I find you on a Saturday morning?
- How do you take your coffee? Or are you a tea person?
- Is there a song you’ve had on repeat lately?
- What’s your favorite place in your city, and why?
- Which app do you use most on your phone (apart from this one)?
- On holiday, do you plan everything or go with the flow?
- Is there a dish you’re really good at?
- What’s the last show or film you told everyone to watch?
- Morning person or night owl?
- Did anything make you smile today?
Curious follow-ups
Once the chat warms up, these show how someone thinks.
- If you could do any job for a day, what would it be?
- Is there a link between what you wanted to be as a kid and who you are now?
- What’s the last thing you changed your mind about?
- What does everyone love that you just can’t get into?
- Is there something you’ve always wanted to learn but haven’t started?
- How would your friends describe you in three words?
- What could you talk about for hours?
- What’s a decision you’re really glad you made?
- Where do you want to go that you haven’t been yet?
- If you had a superpower that only worked for everyday chores, what would it be?
The ones that tell you who someone is
These go deeper. Ask them when you sense the other person is ready, and answer them yourself too.
- What drains you, and what recharges you?
- What’s non-negotiable for you in a relationship?
- What’s something you’ve learned about yourself recently?
- What do you need at the end of a hard day?
- Is there something you’re proud of but rarely mention?
- Which family habit would you like to keep going?
- What’s the last thing that got you really excited?
- What would you like to be different in your life five years from now?
- What do you value most in a friendship?
- What do people get wrong about you when they first meet you?
Fun and slightly odd
For lightening the mood when things get heavy.
- Three things you’d take to a desert island?
- If your life were a film, what would it be called?
- Do you have a silly habit you can’t give up?
- If you were an animal, which one would you be?
- When did you last laugh until it hurt?
- Pineapple on pizza: yes or no?
- If you could live in another city for a day, which would you pick?
- Do you have a karaoke song ready?
- Have you ever become friends with someone totally unexpected?
- Which of these questions would you want to ask me?
Three ways to use questions well
Answer the answer. If someone says they spend Saturday mornings at brunch, don’t just say “Me too!”. Ask “Where? Do you have a favorite spot?”. A follow-up shows you were listening.
Share yourself. Someone who only asks questions sounds like an interviewer. When you ask something, give your own answer when it’s your turn.
Don’t rush. Deep questions feel odd in a first message. Start light and go deeper as the conversation opens up.
How questions work on Solvemate
On Solvemate, this idea is the app itself. Everyone picks four questions about themselves, and you guess how someone answered them. Get all four right and you match. So instead of “Hey, how’s it going?”, your chat starts with something to talk about. Once it opens, the app suggests topics from the answers you share; the messages are always yours.