42 Best First Date Questions to Ask (the Ultimate List)

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Keep the conversation flowing and the awkward silences away with these awesome first date questions, and see if any sparks start to fly with your date.

First Date Questions

Best First Date Questions (questions 1-14 listed below).


1. What achievement are you proudest of?

There’s no better opportunity to show off than on a first date, so give your date the chance to brag a little.

Their answer will give you an idea of the type of achievements that they find impressive.

If it’s a promotion, you’ll know they’re passionate about their career. If it’s a protest or campaign, you’ll know that they prioritize social justice. 

2. If you could travel to one era in history, when would it be?

One of the best ways to make a date successful is to keep the conversation flowing.

Asking interesting questions about hypothetical scenarios will avoid the possibility of any awkward silences and make for riveting conversations. 

3. What’s on your bucket list?

Asking about your date’s bucket list will give you an idea of their future plans, so you’ll know whether you share a view of the future.

You’ll also get an idea of how adventurous they are by what experiences feature on the list.

If you’re afraid of heights and their bucket list consists of skydiving and bungee jumping, they might not be the best fit for you!

4. If you could have dinner with any five people, dead or alive, who would they be?

This quirky conversation starter will guarantee a lengthy discussion, at the same time as giving you an insight into the type of people that your date finds interesting.

5. What was the best day of your life?

Asking about the best day of your date’s life will put them at ease by encouraging them to reminisce about their favorite memories.

You’ll get a clue about what’s important to your date. If the best day of their life took place with family, you’ll know they’re a family-oriented person. If it was a festival or holiday, you’ll know that your date loves adventures.


6. What do you do in your spare time?

Asking about your date’s free time is a simple question to get them chatting. It will also reveal whether you share the same hobbies and interests. 

7. If you were an animal, what animal would you be?

Asking your date what animal they’d be, reveals how they perceive themselves and their main personality traits, helping you understand them better. 

8. What do you do for a living?

It’s common to ask a potential partner what they do for a living early into your first date. 

Their job will dictate other life factors, such as how much free time they have, so it’s a good idea to check that your lifestyles match up before putting a second date in the diary. 

9. Where have you traveled?

Asking about your date’s previous adventures acts as a gateway to stories and anecdotes about their travels, making it a great conversation starter.

You’ll be able to gauge if your interests are similar by the types of destinations and holidays they typically choose. 

10. Do you have any siblings?

One of the first things you’ll usually find out about someone is their family set-up, so this is a typical question to break the ice at the start of the date.

If you’re a family-oriented person and it’s essential that your partner is, how they speak about their siblings can give you an idea of how much they prioritize family.

11. What’s your favorite film?

Most people can name their favorite film off the top of their heads, so asking this as an icebreaker is an excellent opportunity to get the conversation started.

It also gives you an insight into their taste in popular culture and whether it’s aligned with yours.


12. What are your pet peeves?

By inquiring about your date’s pet peeves, you’ll get an idea of what habits and behaviors get on their nerves. If you’re guilty of many of them, you may not be a great fit!

13. Which songs are your guilty pleasures?

If your date is willing to laugh at their own expense and show their sillier side by naming their favorite cheesy tracks, this can be a sign that they’re comfortable in your presence. 

14. What has been your most embarrassing moment?

Telling a potential partner about your most embarrassing moments takes guts. Asking this question will allow you and your date to be vulnerable and humble while probably causing some giggles, bringing you closer together.

15. What’s the best joke you’ve ever heard?

Asking your date about their favorite joke gives you an insight into their sense of humor and whether it’s similar to yours, as well as injecting the evening with some comic relief.

16. What new skill would you love to learn?

Asking this question will give you an idea of what skills and interests your date values and how willing they are to try new things. 

17. What would your ideal weekend look like?

Your date’s dream weekend reveals their favorite things to do in their free time, as well as their lifestyle and whether it’s compatible with yours.

If they love to sleep in on weekends, but you’re an early riser, it’s better to find out sooner rather than later!

18. What’s your dream holiday destination?

Finding out your date’s dream holiday destination gives you clues to their personality. If their dream holiday is on a ski resort, they’re probably quite active and adventurous.

If their ideal destination is a beach in Bali, they likely enjoy relaxing and looking at the beautiful scenery. 


19. What’s your type?

This is a classic first-date question. Asking about a potential significant other’s type reveals the values and characteristics that they look for in a partner.

You can then get an idea of whether you’re well-matched based on how many of their preferred characteristics you have. 

20. What attracted you the most about me?

Now it’s your chance to feel flattered! If your time together is going well, ask what attracted (or attracts) your date to you, to allow them to reflect on what qualities they admire in you. 

21. What’s the cheesiest pick-up line you’ve ever used?

Asking about cheesy pick-up lines gives you the chance to indulge in a bit of playfulness and get an idea of your date’s romantic history. 

22. What’s the most romantic thing you’ve ever done for somebody?

This question allows your date to sell themselves as a romantic partner and gives you an insight into their romantic and affectionate side. 

23. Do you believe in love at first sight?

The answer that your date gives to this question will reveal whether or not they’re an old-fashioned romantic and whether their approach to love is more whirlwind romance or a slow-burn partnership.

24. What’s something I wouldn’t guess about you?

This cheeky question allows your date to reveal as much or as little about themselves as they want.

It also gives you the chance to find out something about them that may not have come up in conversation otherwise. 


25. What would be your dream starter, main course, and dessert?

Asking about somebody’s dream meal is the ideal pathway to talking about food.

You can see if you like to eat the same things, whether or not they have any dietary preferences, and explore their tastes. 

26. What would you do if you had enough money not to need a job?

Not only is this a thought-provoking question prompting an interesting discussion, but it’s also a great way to see how your potential future partner would spend their free time if they had no money-making responsibilities.

If they say charity work, you can count on them being caring and social-justice-focused. If they say they’d travel the world, you’ll know they have an inquisitive side. 

27. What’s the best book you’ve ever read?

Asking about your date’s favorite book gives you an insight into their preferences and whether they’re similar to yours.

You’ll get a sense of how interested they are in literature, which may be a dealbreaker for you. 

28. What’s the worst job you’ve ever had?

Finding out the worst job your date has ever had tells you about their history and how resilient they are when faced with difficulties.

If having a hard-working partner is one of your priorities, you’ll want to pay close attention to their response. 

29. What is your current obsession?

To put your date at ease, give them an opportunity to talk about one of their passions.

There’s nothing people love more than telling others about their interests, and you’ll discover which hobbies you share based on their responses. 

30. How would your friends describe you?

Your date’s response to this question not only tells you how they perceive themself but also how they act around friends.

Their friends will likely have known them for a long time, so you can expect the adjectives they use to be relatively accurate. 

31. Are you an extrovert or an introvert?

Introverts receive energy from spending time alone or with a small group of friends, whereas extroverts feel energized when they spend time with others in a larger group.

If you prefer to stay in on a Saturday evening with a good book, you may be more suited to somebody introverted.

Finding out which lifestyle your date most relates to will help you decide if they’re a good match. 


32. Which object that you own do you feel most sentimental about?

Asking about sentimental objects gives your date the chance to get in touch with their emotional side.

Their response will reveal to you the parts of their life they hold dear and the people around them who they prioritize. 

33. If your life was made into a film, which actor would play you?

Asking which actor would play your date is an excellent way to understand how they view themselves and test their self-awareness.  

34. If you could have any superpower, what would you choose?

This is a playful question that’s sure to prompt hours of discussion. Their answer will tell you more about what your date secretly desires. 

35. What are your favorite song lyrics?

Asking about favorite song lyrics allows the conversation to get deep. Your date’s favorite song lyrics may reveal something about the scenarios they find emotionally compelling.

It will also give you a clue about their music taste, which may be an essential consideration if you’re a music aficionado.

36. Do you prefer to be indoors or outdoors?

You can use this question to find out if your date is the outdoorsy type or a total homebody.

If you spend your weekends hiking and camping, you might prefer to date somebody more outdoorsy, so your date’s response to this question will tell you how similar your lifestyles are.


37. What do you think is your best quality?

Enquiring about your date’s best quality allows them to sell themself and offers you the chance to see if their best qualities match up with the type of partner you’re seeking.

38. What are you afraid of?

This can be a playful or a deep question depending on the response. You and your date may bond over a mutual fear of spiders, or things could get vulnerable if your date reveals a fear of rejection or failure. 

39. Are you a religious or spiritual person?

Find out about your date’s spiritual side by asking them about their belief system. If you’re a religious or spiritual person, it might be important to you that your future partner shares these beliefs.

If not, religion and spirituality make for a fascinating discussion anyway. 

40. What was your childhood like?

Finding out about your date’s childhood and how they were raised may give you an insight into the person they are today. 

41. Who in your life has influenced you the most?

The person who has most influenced your date will reveal how they relate to the world around them.

If it’s a parent, they’re likely a family-oriented person. If a celebrity has most influenced them, they probably admire successful people and may be ambitious. 

42. What brings you fulfillment in life?

Finding out what fulfills your date will give you a strong idea of whether or not they’re a match for you.

If you’re a workaholic, but your date gets their fulfillment from lazy days, you may not have enough in common for another date.

Never let the fear of the conversation drying up on a first date take over, by keeping a generous handful of these first-date questions in your back pocket.

Whether you want your conversation to be thought-provoking, deep, or light-hearted, you can help steer the conversation in a direction that you’re comfortable with.

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Keep these first-date questions for safekeeping, ready for a future date, by saving this article to one of your Pinterest boards.

Best First Date Questions (questions 1-14 listed above).