When I'm preparing for a first date, I want the conversation to feel less like an interview and more like a fun, spontaneous connection. The best first-date questions are the ones that are low-pressure, easy to answer, and get the other person excited to tell a story.

Whether you're dating casually or intentionally, the rule remains: Start easy.

The goal of a first date is simple: Reduce anxiety, find some common ground, and see if I actually enjoy spending time with them. I don't need to discuss deep life plans or emotional baggage—I just need to find the fun and let a natural connection form.

Use 2–3 questions to start off, and then let the conversation flow naturally. You don’t have to use all of them like you are a journalist writing an OpEd on them!

The Golden Rule: Be Genuinely Curious

One golden rule of asking questions is to always ask why or ask them to give more details if they give too short of answer. You are not on a fact-finding mission; you are on an "I wanna know you" mission.

Best Icebreakers & Follow-Up Questions

1. What was the highlight of your week, even if it was something totally small?

People love to talk about their wins, ask them why it was important to them, or how they celebrated. 

2. What's the last song or podcast you got totally obsessed with, and why?

Ask them what about that genre/artist that they usually gravitate towards. This reveals their taste in entertainment and comfort.

3. What's your most useless talent?

Ask when was the last time they actually used that talent.

4. What's a movie you can watch a hundred times and never get sick of?

What about that specific movie that keeps bringing them back? Is it the humor, the comfort, or the nostalgia?

5. What’s your go-to comfort food, and what memory does it bring back?

You can ask if that is a recipe they learned to cook themselves? “Who taught you how to make it?”

6. If you could teleport right now, where would you go for just 30 minutes?

Ask: "What exactly would you do in those 30 minutes? Why that location?" Reveals their travel style or priorities.

7. What's the most fun spontaneous thing you've done recently?

Ask: "Was that something you planned, or did someone else put you up to it?"

8. If you could have an extra hour every single day, how would you actually spend it?

Listen closely to see if they prioritize rest, hobbies, or productivity. Ask: "Is that something you used to do more often?"

9. What's the best recommendation (book, show, travel spot) you've received lately?

Ask: "Who recommended it to you? Are they usually spot-on with their recommendations?" This opens a door to talk about their friends.

10. If you weren't working in your current job, what's a totally random job you think you'd be great at?

Ask: "What skill from your current life do you think would transfer best to that wild new job?"

11. What's a simple thing you are weirdly snobby about?

This could be coffee, pillows, pens, etc. It's funny and specific. Ask: "How did you become so snobby/ knowledgeable/ particular about that one thing?"

12. What’s the next big thing on your bucket list? 

This immediately reveals their appetite for adventure, planning, and future goals. Ask: "What's the hardest part about planning for that, and what are you most excited to learn from it?"

13. If you had an infinite amount of money in the world, how would you spend it? You cannot donate or give it away.

This is a great way to uncover their deepest personal desires and passions beyond money. Ask: "What's the first purchase you would make, and what experience would you spend the most money on?"

14. What’s your favorite app on your phone, other than Instagram?

This reveals practical habits, learning interests, or specific entertainment needs. You can ask how much time they actually spend on it. 

15. What's the absolute worst thing you’ve had to eat recently?

Encourage the humor! Ask: "What was the context? Did someone force you to eat it, or was it a risk you took?" or “How did it go so wrong?”

Bonus from my own notes app

16. Have you ever climbed a tree? 

This is my personal favorite, because I did not know people who never climbed a tree existed. It opens up fun conversations about childhood, or you can just say, “I did not expect you to be such a city person.”

17. What's a simple joy in your life? (Like coffee, dosa, chai, or desserts)

This reveals the small things that bring them peace and happiness. Ask: "Is that a solo joy, or is it something you love to share with other people? How often do you get to enjoy it?"

18. What's a food that everyone seems to love, but you secretly can't stand?

If they say dosa, I walk out. I am kidding, but they will be judged. A great lighthearted disagreement starter! Ask: "Have you ever tried to like it, or is that a hill you'll die on?"

19. If you could choose any fictional place (from a movie or book) to live for one week, where would you go?

This is highly imaginative and reveals the type of environment they find appealing (magic, serenity, action, etc.). Ask: "What kind of activity would you do there on your first day?"

20. What's the worst habit you picked up in the last two years?

A fun way to talk about changes in life. Ask: "Have to tried to quit it? Or is it going to stay?” 

How to Use This List

That’s it! You now have a fantastic list of questions ready to go. Remember, the goal isn't to get through all 20 questions; the goal is to land on one that sparks an incredible story, and then genuinely listen to the answer. The real connection happens in the follow-up, in the laughter, and in the "whys."

If you are going on an intentional date, you should ask a few value questions as well.

Go out there, be curious, have fun, and enjoy the adventure of getting to know someone new!