Match the question to the stage
The right question depends on how well you know each other. Ask a first-chat question on the third hangout and it feels flat. Ask a deep one on day one and it feels like a lot. Below are 72 questions sorted by stage and setting. Pick two or three, not ten.
One rule makes all of them work: answer your own question too. A question followed by your own answer is a conversation. A question followed by another question is an interview.
The first real conversation
You've met once or twice. Keep it about the present and things they chose, not their résumé.
- What's keeping you busy outside work right now?
- How did you end up in this city?
- What's your go-to order here?
- What's the best thing you've eaten this month?
- Are you more of a plans person or a see-what-happens person?
- What were you doing before you got into this (the class, the club, the job)?
- What's something you're looking forward to this month?
- Which neighborhood do you live in, and do you like it?
- What do you usually do on a Sunday?
- What's a hobby you dropped that you'd pick back up?
- What are you watching or reading right now?
- What's the most underrated spot around here?
Over text, between hangouts
Text questions should be easy to answer in one message and leave room for a story. Tie them to something they told you when you can.
What to text a new friend after meeting them
- Did you end up trying that ramen place?
- How did the interview go?
- Settle a debate: is a hot dog a sandwich?
- What song have you had on repeat this week?
- Best thing that happened today?
- What's the worst movie you secretly love?
- Any good plans this weekend?
- Send me one photo from your camera roll this week and explain it.
- Which app do you open first in the morning?
- What's a skill you'd learn if it took no time?
- Coffee or tea, and how do you take it?
- What's your current comfort show?
The second or third hangout
You've covered the basics. Now go one layer down: how they think, what they care about, what their life looks like day to day.
- What does a good week look like for you?
- Who are the people you see most?
- What's something you're proud of that doesn't come up much?
- What were you like as a kid?
- What's a job you'd never want, and why?
- Where's somewhere you've lived or traveled that changed you?
- What's a small thing that makes your day better?
- What's something people assume about you that's wrong?
- If you had a free Saturday and no obligations, what would you do?
- What are you trying to get better at right now?
- Who's a friend you've had the longest, and how did you meet?
- What's a tradition from your family you'd keep?
When you're ready to go deeper
Save these for a walk, a drive or a late conversation, not a loud bar. Frame them so it's easy to pass: 'You don't have to answer this one, but...' And go first if it feels heavy.
- What's something you changed your mind about in the last few years?
- What's been harder than you expected about being an adult?
- Who has had the biggest influence on how you live?
- When do you feel most like yourself?
- What's a risk you're glad you took?
- What do you want more of in the next year?
- What's something you wish more people asked you about?
- What does friendship look like to you? What makes a good friend?
- What's a hard thing you got through that shaped you?
- What are you most curious about right now?
- How do you like to be supported when things are rough?
- What would you do if you knew nobody would judge you?
Fun and random ones
For a lull, a group, or when the mood is light. These work best when you commit to your own answer.
- What's your most useless talent?
- Which fictional place would you live in?
- What's the strangest job you've ever had?
- If you opened a restaurant, what would be on the menu?
- What's your karaoke song?
- What would your walk-up song be?
- What's a hill you'll die on?
- Which animal would you be, and be honest?
- What's the best purchase you've made under $50?
- What did you believe as a kid that turned out to be wrong?
- If you could master one instrument overnight, which?
- What's the weirdest food combination you like?
How to follow up so it doesn't feel like an interview
The follow-up matters more than the question. After they answer, pick one detail and ask about that instead of moving to the next question on your list. 'I grew up near the coast' becomes 'Do you miss it?' not 'Cool. What do you do for work?'
Don't worry too much about how it's going. In studies reported by the Association for Psychological Science, people's new conversation partners liked them and enjoyed their company more than they thought. You probably did better than you think.
What to say when a conversation goes quiet
- Ask for the story: 'Wait, how did that happen?'
- Ask for the feeling: 'Were you nervous?'
- Ask what's next: 'Are you going to do it again?'
- Link it back to you: 'I did something like that once...' then hand it back.
Questions to save for later
Some questions are fine between close friends and land badly early on: how much they earn, why they're single, their politics or religion before you know their views, past relationships, health, and anything about their body. Let them bring these up. If they do, listen more than you ask.
If you like having a question to answer before the small talk starts, HMU profiles each have one, and there's a new question every day. It gives two people something real to say from the first message.
Related articles
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- How to Keep a Conversation Going Over Text (With Examples) — Answer, add, ask: a simple way to keep a text conversation going, with word-for-word replies for dry texts, strangers, new friends, and crushes.
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