40 Questions to Ask When You're Dating Someone New (Light to Deeper)

25 October 2026

If you’re a few dates in with someone new and want better conversation than “so, how was your week?”, this list is for you. Below are 40 questions sorted from light to a little deeper, so you can start easy and only go further when you both feel like it. Pick one, ask it, listen to the answer, then let your date ask you one back. Nobody has to answer anything they don’t want to.

TL;DR

• Start light. Easy, funny questions help both of you relax before anything personal comes up.
• Take turns, so it feels like a conversation and not an interview.
• Passing is always fine. “I’d rather skip that one” is a complete answer.
• Go deeper only when the mood is right. There’s no schedule for when a new relationship should get serious.
• Treat this as a handful of prompts, not a script. Two or three good questions can carry a whole evening.

Before you start: keep it a conversation, not an interview

New relationships have a particular kind of nervous energy. You’re curious about the person, but you don’t want to grill them. A few things help:

• Answer your own question too. If you ask “what’s your ideal Sunday?”, be ready to share yours.
• Follow the interesting bit. If their answer makes you curious, ask about that rather than jumping to the next question.
• Read the room. If someone gives a short answer, it might be a cue to lighten up, not push harder.
• Don’t treat answers as tests. You’re getting to know each other, not scoring each other.

Light and easy: warming up

These are good for a first or second date, or the first ten minutes of any date when things still feel a bit stiff.

1. What’s the best meal you’ve had this year?
2. What’s a small thing that always makes your day better?
3. Are you a morning person, a night owl, or somewhere awkwardly in between?
4. What’s your go-to karaoke song, or the one you’d choose if someone forced you?
5. What’s something you’re weirdly good at?
6. What was the last thing that made you properly laugh?
7. Beach, bush, or city: where do you feel most like yourself?
8. What’s a show or book you could talk about for an hour?
9. What’s your most-used emoji, and what does that say about you?
10. If you had a completely free Saturday with no plans, what would you do?

Getting to know you: everyday life

These dig a little into how someone lives, without getting heavy.

11. What did you want to be when you were little?
12. What’s a hobby you’d love to pick up if you had more time?
13. What does a perfect weekend look like for you?
14. Who’s someone in your life who has shaped you, and how?
15. What’s a food you loved as a kid and still love now?
16. What’s the best trip you’ve ever taken, and what made it good?
17. What’s something you’ve changed your mind about in the last few years?
18. What are you looking forward to over the next few months?
19. How do you like to unwind after a hard day?
20. What’s a tradition from your family or friends that you’d like to keep going?

Values and what matters: a bit deeper

You don’t need to rush into this section. When the conversation is flowing and you’re both comfortable, these questions help you understand what someone cares about.

21. What do you value most in a friendship?
22. What does “a good life” look like to you, in a few years’ time?
23. What’s something you’re proud of that most people don’t know about?
24. How do you like to spend time with the people you love: lots of company, or quiet time together?
25. What’s something you’re working on in yourself right now?
26. How do you usually handle stress, and what helps?
27. What’s one thing you’ve learned from a past relationship or friendship?
28. How important is it to you to have your own space and time in a relationship?
29. What makes you feel really appreciated?
30. Is there anything you’re nervous or excited about in the next chapter of your life?

Playful and a little flirty: when the spark is there

If the chemistry is obvious and you both want to play, these keep things warm and fun without being heavy-handed. Keep it tasteful and let your date set the pace.

31. What’s the most romantic thing you can imagine doing on a rainy afternoon?
32. What’s your idea of a perfect first-date moment, the one that makes you think “yes, this is going well”?
33. What’s a compliment you secretly love getting?
34. What’s your love language, and how would you like to be shown affection?
35. What’s something small a person could do to make you smile?

Looking ahead: gently, with no pressure

None of these are about “where is this going?” They’re simply about shared interests and what you each enjoy.

36. What’s somewhere you’ve always wanted to visit?
37. What’s an experience you’d love to share with someone?
38. What would you do if you had a free week and a small budget?
39. What’s a season or time of year you love most, and why?
40. What’s something you’d like us to try together, just for fun?

How to use these questions

• Pick two or three, not forty. The list is a menu. Choose what suits the moment.
• Take turns. One person asks, both answer, then swap.
• Let either of you pass. Say “pass” or “ask me something else” and move on, with no explanation needed.
• Start light. Begin with the first section and only move down the list if it feels natural.
• Use them anywhere. Over dinner, on a walk, in the car, on the couch.
• Stay curious, not judgemental. There are no right or wrong answers, only information about who someone is.

Things to avoid early on

• Pushing someone to answer after they’ve passed.
• Treating a question as a quiz with a “correct” response.
• Bringing up ex-partners in a way that feels like comparison or interrogation.
• Rushing into heavy topics because a list says you should.

Going slowly doesn’t mean you’re not interested. It usually just means you’re building something properly.

FAQ

What are good questions to ask when you first start dating someone?

Start with light, open ones about food, weekends, travel and favourite things. They’re easy to answer and they show you what someone enjoys. From there, follow their answers.

How many questions should I ask on a date?

Only as many as feel natural. Two or three good questions that turn into proper conversations are far better than a long list fired off one after another.

What if my date doesn’t want to answer?

That’s completely fine. Say “no worries” and move on. Respecting a pass is one of the quickest ways to build trust with someone new.

When should I ask deeper questions?

When you both seem relaxed and the conversation is already open. There’s no set timeline. Some couples get there on the third date, others after a couple of months.

A gentle way to do this together

If you’d rather not come up with questions yourself, Candid is a deck of prompts you draw together on one phone. It has four categories (Icebreaker, Deep Truths, Flirty Dares and Intimate), you take turns drawing, either of you can pass at any time, and there’s no scoreboard. There’s also a Desires match, where each of you picks privately and only mutual choices are shown. Nothing leaves the phone, and no data is collected. It’s for iPhone (iOS 18 or later), and the Icebreaker deck is a handy place to start with someone new.