25 illuminating questions everyone should ask on a first date

The Editors
·6-min read

What with all the nerves and freaking out over what to wear and where to go, thinking of first date questions can tip your pre-date worrying over the edge. Of course, you want to keep conversation flowing, but you also want it to go beyond small talk and into the realm of being able to really get a sense of the person you're dating.

These first date conversation starters, from Dating Expert and Author of Body Language: Learn How to Read Others and Communicate with Confidence, Elizabeth Kuhnke, and Relationship and Sex Therapist Miranda Christophers should let you actually get to know your date without asking boring old questions.

So once you've figured out what to do on your first date, here's what to talk about and the right questions to ask, with expert commentary on how the questions will help you to understand your date better.

1. If you could travel anywhere, right now, where would you go?

"If the answer is 'nowhere', you’ve got yourself a hermit. If the question elicits a string of destinations, you’ll discover what excites and appeals to them," Elizabeth says.

2. What’s something you want to learn/ get better at?

"This question would enable you to understand if the person wants to develop or better themselves and how. It might show the person's interests and aspirations - you can think about whether these align with yours and how you feel about it," Miranda says.

3. What's something I wouldn't guess about you?

"This question has a bit of mischievousness and flirtation about it, and you’re giving your date the freedom to reveal as much, or as little, as they want," Elizabeth says.

Photo credit: Getty
Photo credit: Getty

4. What's your favourite place on Earth?

"This might help you get a glimpse of their lifestyle as it could indicate the places they want to go on holiday to or how they would like to live," Miranda says.

5. What's your dream job?

"You’ll find out what motivates and inspires them, while discovering values and character qualities that may (or may not) match yours," Elizabeth says.

6. What's something you're proud of?

"This question can give insight into what is meaningful for them and might demonstrate their values. It's a chance for you to see their self-awareness, too," Miranda says.

Photo credit: Henrik Sorensen
Photo credit: Henrik Sorensen

7. If you didn’t have to work to support yourself, how would you spend your time?

"This tells you about the other person’s values and interests. If they don't match yours, better to know now than later on down the road," Elizabeth says.

8. Is there anything you don't eat?

"On a practical note this could avoid any awkward dinner date moments. However it might also highlight any ethical/cultural/lifestyle differences you might have that you don't think you would be comfortable with. It could also indicate how adventurous or fussy they are," Miranda says.

9. What appeals to you most about living here?

"You'll find out what you have in common, or don’t. If you find that you do share common interests, you have an arsenal of ideas for future dates," Elizabeth says.

10. What did you want to be when you were growing up?

"It's always good to know if you're dating a potential superhero," Miranda jokes. "It gives a glimpse into their inner child and may tell you more about their personality and journey, such as if they went on to do what they aspired to do."

11. Can you tell me about your family?

"How they answer gives you insight into their background, upbringing, and what they value," Elizabeth says.

12. Tell me about your friends?

"If you’re looking to enter into a relationship with someone, be advised that you’re also entering into a relationship with their friends. Plus, being able to talk about other people takes the pressure off of your date," Elizabeth says.

Photo credit: Westend61 - Getty Images
Photo credit: Westend61 - Getty Images

13. What are your favourite TV shows?

"People’s interests are reflected in what they like to watch. If they devote hours to watching the news and you only tune in for sports highlights, you’ll find out soon enough if you stand a chance for future dates," Elizabeth says.

14. If your life were a movie who would play you?

"This is an opportunity to find out how they see themselves, and get a sense of their character traits to see if they appeal to you," Miranda says.

15. What do you like to read?

"People’s interests and curiosity reveal themselves in their choice of reading material. Finding out what people like to read reveals their intellectual interests and passions," Elizabeth says.

Photo credit: Ana Maria Serrano
Photo credit: Ana Maria Serrano

16. If you could be anyone for a day, who would it be?

"The answer to this question might reveal more about their personality and motivations/inspirations, plus the qualities they admire," Miranda says.

17. Who has been the most influential person in your life?

"Discovering who and what that person did that mattered so much reveals the other person’s values , family dynamics, and close relationships with friends," Elizabeth says.

18. What's your favourite memory?

"The answers could tell you more about who they are, what is meaningful for them and what they enjoy," Miranda says.

19. Do you still keep in touch with childhood friends?

"How your date responds gives you insight into how they value relationships and loyalty," Elizabeth says.

20. If you could have a superpower what would it be?

"This might tell you more about the way someone thinks and what they desire," Miranda says. People's reactions to curve-ball questions can be really telling - it gives you the chance to see how they respond to you presenting the unexpected. Do they embrace the question or make you feel a little awkward for asking it? Noticing how they make you feel in the way they respond can help you to get a sense of whether you like them."

21. What’s the most spontaneous thing you’ve ever done?

"If you want to discover how flexible, risk-taking, thrill-seeking a person is, this is the question to ask," Elizabeth says.

Photo credit: We Are
Photo credit: We Are

22. What would you do if there was zombie apocalypse right now?

"This a fun ice-breaker that might tell you a bit about their sense of humour, creativity, survival skills or how they would approach challenges," Miranda says.

23. What were you like as a child?

"Shy? Bashful? Full of beans? This gives you a hint of what kind of person they are today," Elizabeth says.

24. Is there anything you're really passionate about?

"An easy way to find out if the person has strong feelings or is more laid back with milder feelings," Elizabeth says.

25. What's the worst pickup line you've ever heard/dished out?

"Why waste time with someone who doesn’t enjoy a bit of flirtatious fun? Friendly banter and shared laughter are signs that you see life in a similar way," Elizabeth says.

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