Fun Questions to Ask: 70 Conversation Starters for Dates, Texting and Couples

Quick answer: the best fun questions are open-ended, easy to answer and invite a story: “What’s the best thing you ate this month?” beats “Do you like food?”. Ask one, listen, then ask a follow-up about their answer before you move on.

A good question does two jobs. It gives the other person something easy to talk about, and it shows you’re curious about them rather than waiting for your turn. The lists below are grouped by situation, so you can pick the right tone for a first date, a text thread or a long-term relationship.

How to use these questions without sounding like an interview

Follow up before you switch topics. If they say their dream trip is Japan, ask what’s pulling them there before you jump to the next question. Two or three follow-ups on one topic feel like a conversation; ten new questions feel like a quiz.
Answer your own question. Share your answer too. It keeps things balanced and gives them something to react to.
Match the setting. Light questions suit a loud bar or a first text. Save the deep ones for a quiet walk or a third date.
Let silence breathe. A short pause isn’t failure. People often add the most interesting detail after a beat.
Skip anything that sounds like screening. Questions about exes, salary or “where is this going” can wait until you know each other.

Fun first-date questions

What’s the best thing you’ve eaten this month?
What’s a hobby you picked up and dropped within a week?
If you could master one skill overnight, what would it be?
What’s your go-to karaoke song, even if you’d never actually sing it?
What’s the most “you” thing you did last weekend?
Which place in this city would you take a visitor first?
What’s a small thing that instantly makes your day better?
Are you a planner on holiday, or do you wing it?
What’s a film you can rewatch forever?
What’s the strangest job you’ve ever had?
If you had a free Saturday and no budget, what would you do?
What’s something you’re weirdly good at?
What did you want to be when you were ten?
What’s the best concert or live event you’ve been to?
What’s an opinion you hold that most people disagree with? (Keep it light: pineapple on pizza counts.)

Funny questions that break the ice

What’s the most useless fact you know by heart?
Which fictional character would be the worst roommate?
If animals could talk, which one would be the rudest?
What’s your most irrational fear?
What’s the worst haircut you’ve ever had?
If your life had a theme song, what would it be?
What would your autobiography be called?
What’s the silliest thing you’ve cried at?
Which emoji do you use way too much?
If you were a sandwich, what would you be?

Questions to keep a text conversation going

Texting rewards questions that are quick to answer but leave room for more. Photos help too: “What does your view look like right now?” invites a reply in seconds.

What’s been the highlight of your week so far?
Coffee, tea, or something chaotic?
What are you watching at the moment?
What’s on your plate for dinner tonight?
Morning person or night owl? Be honest.
What’s a song you’ve had on repeat lately?
What’s the best thing on your phone’s camera roll from this month?
Beach holiday or city break?
What’s one thing you’re looking forward to this month?
Would you rather be able to fly or be invisible, and what would you do first?

Deeper questions for when you’re getting closer

These suit the second or third date, once you’ve laughed together and the conversation is flowing.

What’s something you’re proud of that most people don’t know about?
Who has influenced you the most?
What does a perfect ordinary day look like for you?
What’s a lesson you learned the hard way?
What makes you feel most at home?
What’s something you’ve changed your mind about in the last few years?
What would you do if you knew you couldn’t fail?
How do you like to be cheered up after a bad day?
What’s a tradition you’d love to keep or start?
What are you most curious about right now?

Want to go deeper still? In 1997, psychologist Arthur Aron and colleagues published a set of 36 questions that gradually increase in personal depth. In their study, pairs of strangers who worked through the questions reported feeling closer than pairs who made small talk. (Aron et al., 1997)

Fun questions for couples

Long-term partners can run out of new things to ask. These make good conversation on date nights, road trips or lazy Sunday mornings.

What’s your favourite memory of us so far?
When did you first realise you liked me?
What’s a trip we should take in the next year?
What’s one thing I do that always makes you laugh?
If we swapped lives for a day, what would you do first?
What’s a new hobby we could try together?
Which song reminds you of us?
What’s the best date we’ve ever been on, and why?
What’s something small I could do that would make your week easier?
Where do you see us living in ten years?
What’s a meal we should learn to cook together?
What did you think of me the first time we met?
If we had a family motto, what would it be?
What’s a goal you’d like me to help you with?
What’s one thing you’d like us to do more of?

“Would you rather” questions

These work in almost any setting because there’s no wrong answer and the follow-up writes itself: “Why?”

Would you rather live by the sea or in the mountains?
Would you rather have a personal chef or a personal driver?
Would you rather relive one day forever or skip ahead five years?
Would you rather know every language or play every instrument?
Would you rather travel back in time or into the future?
Would you rather only watch comedies or only watch thrillers for a year?
Would you rather have a dog that talks or a cat that does chores?
Would you rather never use social media again or never watch TV again?
Would you rather spend a weekend camping or in a five-star hotel?
Would you rather be famous for something silly or unknown for something brilliant?

What not to ask early on

Some topics are fine eventually but feel like pressure on a first or second date:

Detailed questions about past relationships or why they ended
Money, salary or debt
“Why are you still single?”
Questions about their body or appearance
Plans for marriage or children, unless they bring it up

If the other person brings up a sensitive subject, follow their lead and keep your tone kind and curious.

Frequently asked questions

How many questions should I ask on a first date?

There’s no number. Aim for a roughly even split of talking and listening. If you notice you’ve asked several questions in a row without sharing anything yourself, answer one of your own.

What if they give one-word answers?

Try a more open question (“What’s the story behind that?”) or switch to something you can both react to, like the food, the venue or the music. Some people warm up slowly. If they still don’t engage after a while, that tells you something too.

Are these questions good for online dating apps?

Yes. Questions about something in their profile work best, because they show you actually read it: “Your photo from that hike looks great. Where was it?” is better than a generic opener.