A couple early in a new relationship, seen from behind walking side by side down a quiet street under pink blossom trees, their hands about to touch

The best questions for a new relationship start light and get deeper as you settle in. Below are 60 of them, from easy first-date openers to a few gentle check-ins about the two of you.

You’ll learn plenty just by spending time together. How they take their tea. What they do when they’re nervous. Which friend they call first with good news. A good question simply speeds that up and makes the time feel richer.

The trick is pace. A question that feels lovely on the tenth date can feel like a lot on the second, so they’re grouped in roughly the order they tend to fit.

Roughly the order they tend to fit

Light ones first. Gentle check-ins about the two of you last.

  1. 1 to 12Early datesLow stakes, and good at starting a story.
  2. 13 to 24Their worldThe people, places and routines that come with them.
  3. 25 to 36What mattersOnce you’ve settled in a little.
  4. 37 to 48How they like careSaves well-meant gestures that miss.
  5. 49 to 60The two of youA few weeks or months in.

What to ask on the first few dates

These are low stakes and good at starting a story. If you only use one section, make it this one.

  1. What did you do last weekend that you actually enjoyed?
  2. What do you always order at the place you visit most?
  3. Are you a planner, or more of a see-where-the-day-goes person?
  4. What’s something you’re surprisingly good at?
  5. What job did you want as a kid, and how close did you get?
  6. What was the best meal you had this year?
  7. Morning person, night owl, or neither?
  8. What small thing lifts your mood almost instantly?
  9. What are you watching or reading right now, and would you recommend it?
  10. Which spot around here do you think is underrated?
  11. What trend have you never quite understood?
  12. What’s the last thing you got really excited about?

Questions about their world

Once the small talk flows, get curious about the rest of their life: who’s in it, where they go, and what a normal week looks like.

  1. Who do you talk to most in a normal week?
  2. Does your family have a nickname for you, and is there a story behind it?
  3. What was your neighbourhood like growing up?
  4. Which friend has known you the longest?
  5. Walk me through a normal workday, start to finish.
  6. What are you working towards at the moment, big or small?
  7. What do you do with a free evening all to yourself?
  8. Is there a tradition from home that you still keep?
  9. Which of your friends do you think I would get along with first?
  10. What do people usually get wrong about your job?
  11. How would you describe teenage you in one sentence?
  12. Where do you go when you need a change of scene?

Questions about what matters to them

Save these until you’ve settled into each other’s company a bit. And answer them yourself too, because it’s only fair.

  1. What do you want more of in your life this year?
  2. Which quality in your closest friend do you wish you had more of?
  3. What’s a small risk you took that paid off?
  4. What makes a day feel well spent to you?
  5. Is there a cause or topic you care about more than people might guess?
  6. What do you enjoy spending on, and what do you like to save for?
  7. What does being a good friend mean to you?
  8. Who taught you something that has stuck with you?
  9. What are you proud of that you rarely mention?
  10. How much time on your own do you need to feel like yourself?
  11. What does home mean to you right now?
  12. Is there a rule you try to live by, even loosely?

How do they like to be cared for?

Everyone gives and receives care a little differently. Knowing early saves a lot of sweet gestures that miss.

  1. When something goes well for you, how do you like to mark it?
  2. When you’re stressed, do you want company or quiet?
  3. Between plans, do you prefer calls, texts, or voice notes?
  4. What kind of gesture makes you feel appreciated?
  5. How do you honestly feel about surprises?
  6. What’s the best way to cheer you up after a rough day?
  7. What does a relaxed Sunday look like for you?
  8. Is there anything you’re sensitive about that it would help me to know?
  9. After a disagreement, do you like to talk straight away or cool off first?
  10. What small thing makes you feel looked after?
  11. How much of your life do you like to share online?
  12. What helps you feel settled when life gets busy?

Gentle questions about the two of you

These are for a few weeks or months in, when you both want to know where you stand. Ask kindly, and be ready to answer too.

  1. What was your first impression of me, honestly?
  2. What moment made you want to see me again?
  3. What has been your favourite time together so far?
  4. What’s something you’ve always wanted to do but never had anyone to do it with?
  5. How often would you like to see each other in a normal week?
  6. Is there anything you would like a little more of, or less of, from me?
  7. How do you feel about meeting each other’s friends?
  8. What pace feels right to you for this?
  9. In general, what are you hoping for from a relationship?
  10. What have you enjoyed learning about me so far?
  11. Is there anything you’ve been curious about but haven’t asked yet?
  12. What would make the next month feel good for both of us?

How do you ask questions in a new relationship without it feeling like an interview?

Sixty questions is a lot, and nobody wants to feel quizzed over dinner. This is what keeps it easy.

  • One or two per date is plenty. When a topic takes off, follow it and forget the list.
  • Go first sometimes. Offering your own answer shows you’re not asking anything you wouldn’t share yourself.
  • Listen for the second answer. The first reply is often the polished one, and a soft “how come?” usually brings out the real one.
  • Notice what they ask back. Curiosity running both ways is one of the nicest early signs.
  • Let people pass. Some topics take longer to feel safe. A skipped question tells you something too, and it deserves respect, not pressure.
  • Trust how you feel. If an answer leaves you uneasy, you’re allowed to slow down and take your time.

Where Our Little Thing fits

If you enjoy this kind of thing, Our Little Thing gives you one question a day. You each answer on your own, and neither answer shows until you’ve both replied. Then you see them side by side. Choose Romantic partner when you set it up, and one question pack is free to start. There are Close friend and Family options too.

It works on one phone you pass back and forth, so nobody has to get serious about apps on date three. Later, if you both want to, you can pair two phones. Creating the invite is part of Premium, and the person you invite joins without paying.

Not ready for an app yet? That’s fair. Our free question of the day gives you one new question every day, so you can ask it tonight.

Once you know each other a little better, move on to the 100 questions to ask your partner. For something playful on date five, our would you rather questions for couples are an easy laugh. And when you’re ready for a night in, pick one of these cheap date night ideas at home.

Questions people ask

How many questions should you ask on an early date?

Two or three good ones is plenty. Let each answer turn into a proper conversation, share your own answer too, and leave room for the rest of the date.

What questions are best avoided in the first few dates?

Anything that feels like a background check, like detailed questions about exes, money or someone’s hardest memories. Those talks matter, but they go better once there’s some trust between you.

When should you talk about what you both want from the relationship?

There’s no fixed rule. Lots of people find it comes up naturally after a few weeks of seeing each other regularly, or sooner if one of you is unsure. Asking kindly and early saves you both a lot of guessing.

Is it strange to use a list of questions with someone new?

Not at all, as long as you use it lightly. Saying you found a list and picked your favourite is honest and often funny, and it takes the pressure off you both.