6 Perfect Questions You Can Ask During a First Date

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The first date is one of the most important parts of any romantic relationship. It is usually when you get to know someone and decide if they are worth your time or not. If it goes well, then things progress and if it does not, then you may be spared a lot of heartaches later down the road.

The objective of the first date is to not only learn more about your date, it is also to be able to present yourself in a fun and engaging way that a second date will happen between the both of you, should you wish upon it. The sort of questions that are asked on the first date should be both fun and engaging.

All these questions are technically ‘canned questions’. You can always just keep them ready and fire them off one at a time when the conversation gets dry. And the best part is that you can always use them for every next person you meet! One key element to keep in mind is that they would usually ask you back these questions after they had answered them. 

Do not forget the key idea of having fun – you have to have a decent or splendid answer to these questions. It is best to roll with these questions with a story from your past or a really good reason why you feel passionate about these things.

We have compiled a list of 6 perfect questions that you can ask on a first date which are engaging, fun, and help you get to know someone on a deeper level:

1.If you had a choice to live anywhere in the world, where would it be? Why?


Singapore is a small place, packed and fast paced. Many people would love to leave the country and live elsewhere. Especially watching sitcoms on TV, it really gives us an insight of the kinds of places available out in the world. 

Asking this question usually gets the feedback of “I cannot move because my family is in Singapore.” Affirm the hypothetical and press on – ask where would she really want to spend the rest of her life, given no obligations.

2.If you can pick up a new skill, what would that be? Why so?


Everyone has something they want to achieve. Be it playing the guitar, dancing or learning to fly a plane. In life, we usually put away these “passions” to make time for work and the people around us. Our own needs and wants are usually forgotten. 

Asking this question would give you a deeper understanding of what she wants to do. Who knows? If she says learning to sing, the both of you can even sign up for singing lessons on the next date!

3. What are you most passionate about?


Passion makes the heart grow fonder. You can get to know so much more about someone when you delve into what makes them happy, and what drives them. Everyone loves to talk about what they are passionate about. By discussing this, you can even find out if you share similar passions. 

Most of us would not be working in the job we are currently in if we ever had the chance. This question gives her the opportunity to fantasize about her dream career and it gives you a good idea on what she is really passionate about.

4. Do you have a bucket list? What is on it?


Staying on the topic of passions, a bucket list is another way to talk about desires and wants that your date has.

A bucket list includes desires outside of a work-life, and is more of personal interests and accomplishments. You can get to know the other side of your date by talking about what they want to do in life apart from their career.

5. What makes you laugh?


You do not want to ask all serious questions that can make it seem like an interview, a question like “what makes you laugh?” clears the air a little more and makes room for some joke exchanges.

You can learn about your date’s sense of humor, and whether or not it matches yours. You can even learn about what makes them laugh, and continue doing or saying things that will keep them giggling all along. 

6. How good were you as a kid?


Everyone was a “good kid”. There are (of course) exceptions, but generally kids always want to be the ‘“nicest” version of themselves. This is a good question to ask as it always pries at their outlook of who they think they are and their perceived version of themselves. 

Generally, people can only go at it from 2 angles, whereby they can say they are still a “good” person today or they are matured and have more insight in life. This can serve as a good source of insight, if they are still putting on a facade in life.

Know that these questions are meant for “fun” and not taken too seriously. The best part of these questions is that there is no “right answer” to them. And unlike political, money-oriented, religious topics, these cannot be taken too seriously. 

These questions are”‘canned topics”, which means you already know your answers to these questions. There is a high chance that your answers will be a lot more profound and solid than hers, especially if you have been using them for a while. 

Over time, you will refine the answers to these questions more. Do keep in mind to listen to her end of conversation, using the 80/20 rule in conversational ratios to do more listening than “preaching”. 

You can always increase the list of questions and create some of your own. Know that the intention is to be fun and engaging. The best kinds of questions are not “yes/no” answers, but rather ones that probe your (and your partner’s) imaginations.

Want more advice about how best to get to know someone? CGull has been helping people navigate Singapore’s dating waters by offering dating coaching services. Our team of experts is ready and waiting to help you get through your next date with the utmost confidence.

Contact us today!

1 thought on “6 Perfect Questions You Can Ask During a First Date”

  1. Pingback: How To Ditch The Awkward Silences On Your Next First Date - CGull

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