Things to Talk About With Friends (For Every Kind of Night)
80+ things to talk about with friends when you are bored, over text, on a call or at dinner, from funny hypotheticals to deep questions, sorted by situation.
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The best things to talk about with friends are the ones that invite a story instead of a yes or no: the best and worst part of their week, something they have changed their mind about, a plan, a memory, or a ridiculous hypothetical. Below are more than 80 conversation starters sorted by situation, from bored on a Tuesday to a long dinner, plus how to keep the conversation going once it starts.
Use them loosely. Nobody wants to be interviewed by their friend with a list. Pick one, ask it like you actually want to know, and let it wander.
When you are both bored
- What's something you've been weirdly into lately?
- If we had to start a business together tomorrow, what would it be?
- What's the most useless skill you have?
- What's a hill you'd die on that nobody else cares about?
- What would you do with a completely free Saturday and no money limit?
- What's the last thing you looked up at 2am?
- Which fictional place would you actually move to?
- What's a small thing that makes your day better every time?
- If you could instantly master one thing, what would it be?
- What's the best thing you've eaten this month?
Over text
Text is for light openers that are easy to answer in one message. Save the heavy questions for when you can hear each other.
- “Settle this for me: is cereal a soup?”
- “What are you watching at the moment? I need something new.”
- “Rate your week out of 10. I'm a 6, explanation available on request.”
- “Saw this and thought of you” (with a photo, a song or a meme).
- “What's one thing you're looking forward to this week?”
- “Unpopular opinion time. Go.”
- “If you had to describe today as a weather forecast?”
- “I need a book recommendation and I trust your taste.”
- “What's the most chaotic thing that happened at work this week?”
- “Remember when we… ?” (finish it with any shared memory)
On a call
Calls give you tone of voice, which means you can go a little further than you would over text.
- What's been taking up most of your head lately?
- What's the best and worst part of your week so far?
- What's something you're proud of that you haven't told anyone?
- What are you avoiding at the moment?
- What does a normal day look like for you right now?
- Who's someone you've met recently who surprised you?
- What's something you want to do before the end of the year?
- What would make next week a good week?
- What's a decision you're stuck on?
- What's the funniest thing that's happened to you since we last talked?
At dinner or over drinks
- What's a meal you'll remember for the rest of your life?
- What's the best advice you've ever ignored?
- Where were you this time five years ago, and would that version of you be surprised now?
- What's a tradition you'd like to start?
- Who's the most interesting person you've ever sat next to by chance?
- What's a plan we keep saying we'll do and never actually do?
- What job would you do if money didn't matter at all?
- What did you believe as a kid that turned out to be completely wrong?
- What's a place you want to go back to, and why?
- Which friend from the past do you still think about?
Funny questions and would-you-rathers
- Would you rather always be ten minutes late or always be an hour early?
- Would you rather have a rewind button or a pause button for your life?
- What's the most embarrassing thing you did as a teenager that still haunts you?
- If animals could talk, which one would be the rudest?
- What would your walk-out song be?
- Which celebrity would you trust to look after your plants?
- What's the worst haircut you've ever had?
- Would you rather fight one horse-sized duck or a hundred duck-sized horses?
- What's a completely normal thing you find strange?
- If your life were a sitcom, what would the title be?
A bit deeper
You do not need a special occasion for these. In a 2022 study, Michael Kardas, Amit Kumar and Nicholas Epley found that people consistently underestimate how much others will enjoy a deeper conversation, and expect it to be more awkward than it turns out to be.
- What's something you've changed your mind about in the last few years?
- When do you feel most like yourself?
- What's something you wish people asked you about more?
- What are you still figuring out?
- What's a fear you've grown out of, and one you haven't?
- Who has shaped you the most, without them knowing?
- What does a good life look like to you right now?
- What's something hard you're glad you went through?
- What do you need more of at the moment?
- What's a question you'd love someone to ask you?
If you want to go further, 70 deep questions to ask friends goes from light to properly deep.
Catching up after a while
- What's the biggest thing that's changed since we last properly talked?
- What are you into now that you weren't back then?
- What's been the best bit of the last year?
- What's been harder than you expected?
- Who are your people at the moment?
- What are you looking forward to?
- Do you still think about that night at…? (fill in your shared memory)
- What should I know about your life right now that I probably don't?
If the gap has been long enough that you are not sure how to start, how to reconnect with old friends has messages for every kind of silence.
When one of you is having a hard week
This is less about topics and more about giving them room. Ask, then mostly listen.
- How are you actually doing? Not the polite version.
- Do you want to talk about it, or do you want distracting?
- What's the hardest part right now?
- Is there anything that would make this week even slightly easier?
- Do you want advice, or do you just want me to listen?
- What can I take off your plate?
That last distinction matters more than any question. How to support someone who is venting explains why fixing is often the wrong move.
Big-picture and what-if questions
- If you could live in any decade, which would you pick?
- What do you think people will find ridiculous about us in 50 years?
- If you could know one thing about the future, what would you ask?
- What would you do differently if nobody could ever judge you for it?
- Which invention would you un-invent?
- If you could swap lives with anyone for a week, who and why?
- What would your ten-year-old self think of your life now?
- What's a rule everyone follows that you think is pointless?
- If you wrote a book, what would it be about?
- What do you hope people say about you when you're not in the room?
How to use these without it feeling like a quiz
- Answer your own question first sometimes. “I've been weirdly into sourdough lately. What about you?” makes it a swap, not an interview.
- Follow up once before moving on. “Wait, why that one?” is worth more than three new questions.
- Let it drift. The question is a door, not a script. If it leads somewhere else, go there.
- Match the moment. A deep question in a loud bar lands badly. A funny one on a hard day can be exactly right, or exactly wrong. Read the room.
- Leave silences alone. In a close friendship, quiet is not failure. It is often trust.
If conversations tend to stall after the first answer, how to keep a conversation going is about the follow-up habit that fixes it.
Where Spillr fits
Spillr is not a chat app for your existing friends. But if you like the slower, more honest kind of conversation, Scrolls are built for it: you write one letter a day to one person on Spillr, they can write back once within a week, and if you both press your seal, you keep talking. A question from the deeper section of this list makes a very good first line. Strangers tend to answer honestly when they have nothing to protect.
The short version
Ask for stories, not facts. Go first when you can. Follow up once. And remember the real goal is not to fill the silence. It is to find out something new about someone you already like.
Questions people ask
What do you talk about with friends when you run out of things to say?
Swap facts for stories. Instead of “what did you do this week?”, ask “what was the best part of your week?” or “what's something you've changed your mind about lately?” Questions that invite a story keep going on their own. A shared plan or a ridiculous hypothetical also works, because there is no right answer to run out of.
What can I talk about with friends over text?
Things that are easy to answer in one message but leave room for more: a photo of something that reminded you of them, a quick poll (“settle this: is a hot dog a sandwich?”), a recommendation request, or a small honest update. Text works best for light openers. Save the big questions for a call or in person.
How do you have deeper conversations with friends?
Go one step deeper than usual and go first. Share something slightly real about yourself, then ask a question with some room in it, like “what's been taking up most of your head lately?” Research by Kardas, Kumar and Epley found people consistently underestimate how much others enjoy deeper conversations, so the awkwardness you expect is usually smaller than you think.
Is it normal to run out of things to talk about with close friends?
Yes. Quiet is not a warning sign in a close friendship. Comfortable silence is often a sign of trust. If every catch-up feels flat, though, it can mean you are both stuck on updates rather than stories, and changing the type of question usually fixes it.