High quality questions to ask on a date that will help you know if the person in front is the perfect match for you, know their inner-self better and make your conversation more interesting


Check out part one of this article (here) if you haven’t gone through it. It will help you get a better understanding of this article. High quality questions to ask on a date that will keep your conversation more interesting, connect both of you faster and earn you more points

When you start a conversation on a date, you’re having a straight-line conversation – so the type of questions you ask might drop or rise the graph of your conversation. We have already talked about much on the first part of this article. People run out of things to say & start focusing on facts. Facts are boring, they don’t create any newness for example; what do you do, how many brothers and sisters do you have, do you know how to drive, do you go to church, your longest relationship & how it went, how many kids do you want? (You can ask such things later but not on the first dates) Such facts won’t give you the right information whether the person in front is a good match for you & won’t reveal who really that person is. Don’t make it sound like you’re interrogating them, like some sort of an interview. Facts lead to a disconnection.

Like I said already, going on dates isn’t just about impressing each other, it’s also finding someone you wanna invest in. So, talk about future plans. This shows also you’re an ambitious person. Also shows seriousness because the two of you are all about the future and this creates curiosity together.

Your questions should be concerned with knowing the deeper self of the person.

 The aim is to connect faster on your introduction. If you’re a man, prepare her first. For instance, make it into sort of a game so that it becomes fun & not just random questions in a conversation. To make it a game say; ‘rules of the game – if you have a question about me, let it wait till it’s your turn to ask & you have to answer 100% honestly’.

Don’t use all the questions on the date too because too much will also be boring, just be strategic and creative. And respect the answer they give because it’s supposed to be fun.

If they start talking about family ask about family, if it’s travel ask about travelling so as to keep them connected to the interest they initiated. Don’t keep them trapped in their bad or good memories during this conversation because you might lose the fun of the game.

How does a typical day look like to you? You don’t need to ask about their career, such questions will give background to their daily routines.

Why is your best friend your best friend? It shows you care about the people they’re close to and you want to know what they value most in friendship.

Who is your hero? This defines what they value most in a person of meaning in the society.

What are some of the things that make you laugh? Trying to figure out what defines her fun.

If you have to change one thing in this current society, what would that be? To know how they view the society negatively or what they don’t like about society.

What’s that one book you read or documentary film you watched that had a significant impact on your life? This is much more practical than just asking, ‘Your favorite movie or book you ever read and why?

You biggest goal in life? This helps you know how they define the purpose of being alive on earth.

What has your mom/dad taught you that you still use to this day? I’d like to learn from your family through you. This is just to know how their parents have molded them.

What’s one thing you wish your mom/dad taught you? Trying to figure out their regrets and see what makes them lonely or how they resent life because of their background.

What’s the story behind that scar on your hand? …or; story behind those shoes? I like them! If it’s about the scar then you just want to know about their drama they encountered, if it’s about shoes or dress toy just want to know their taste for fashion.

What’s been your highest high or your lowest low, the point when your life was so amazing or so sucking? …or; what was the best or the worst part of your life? Just exploring deeper to know how they define happiness or sorrow at their worst level. You can ask these questions separately, not both at the same time like I have put it.

The toughest struggle you went through that you didn’t know you would make it out but you did & how did you come out of it? This question helps you know about their fortunate moments and how they define being strong.

Tell me either the weirdest thing or the best thing about you that most people don’t know. They might not want to talk about such on first dates but how you bring it up decides on how they respond.

What’s one of your secrets I don’t know yet. This is an open-ended question which is of free will so they won’t feel forced. They might tell you negative or positive (story or just straight answer) Whatever the answer they give, it’s sure to start an interesting conversation.

What should I know about you that I’d never think of asking about? This goes a little deeper but it’s better when you ask later after you’re closer to each other.

What’s the craziest most spontaneous thing you’ve ever done… or encountered and how did you react? Helps you know if they’re your kind of crazy and how they react to spontaneous (unexpected) occurrences.

Would you rather live in the city where people are many and busy or in the woods where it’s just you and few friends you know with quietness? …or if you could live anywhere, where would it be? This question focuses more on the type of lifestyle they desire…

If I gave you a 100 thousand dollars right now, what would you do with it? It doesn’t matter what answer they give though; whether they would fill their word rope or start a business, matters not. You’re just checking to see their habit of spending.

If you could take a two-week vocation in the world anywhere, where would you go? Getting their ideal place of escape will give you an idea of what stresses them out because vocation is mostly to relieve people.

What does family mean to you? Talk about their family and their desires for family.

What has made you cry in the recent years …or; when was the last time you cried? This is to know what brings tears to their eyes and what crying means to them so long as pain is concerned.

What was the difficulty in your childhood? You’re trying to get the drama of someone’s childhood and probably what would have shaped their view of the world today.

What do you regret? It will reveal where they messed up, if they’ve moved on or not and it was their mistake or they blame someone for it.

To who would you like to go back and apologize if you had to? …or; What would you like someone to forgive you for?  If they hurt someone but they were too proud to say sorry or didn’t find that chance to say sorry and they still feel haunted. Also, to know what’s wrong with them emotionally, and how they can cause trouble to people.

What have your exes never understood about you? Things that led them to break up because of being misunderstood. Past relationships are clues for success of future ones… what they’ve learnt and are ready to apply.

Have you ever accused someone falsely without knowing they were wrong then later realized it & how did you handle it? To know their level of pride or humility when it comes to facing their faults.

What would you ideally want to tell any member of your family? What they have to appreciate about the that person who means most to them in their family.

In what ways do you feel like a bit of an imposter at work? Perhaps to check their level of competence and how they perceive work.

Check out part one of this article (here) so, you can get to know questions that will help you know how to keep the conversation more interesting and get you connected much faster. High quality questions to ask on a date that will help you know if the person in front is the perfect match for you, know their inner-self better and make your conversation more interesting


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