What To Expect On Your First Date & 17 Questions to Ask on a First Date

17 Questions to Ask on a First Date

When you first meet a guy it is never easy to get the answer you want from your date. First meetings are usually an exchange of expressions and both understand each other.  

Dating is never easy but we are here to help by providing you with some sample questions you can use to ask on a first date. Just remember though, that it’s equally essential to LISTEN as it is to find the answer to these questions. 


So when on a date and the other person is talking, ensure you are actually hearing what they say, not just waiting for them to finish so you can ask your next question.

17 Question To Ask On First Date:

People often get confused when they are on their first date, their confusion leads them to ask something stupid. That is why we have compiled these seventeen questions to ask on your first date. These questions are from Rebecca Perkins, who you can follow on  Twitter @themidlifecoach.

1. What’s one thing you wish you’d known 20 years ago?

Past ambitions and regrets are always a good start to conversations. When you ask a person about his regrets and experiences, it means you are digging for how consistent the person was with his life and how much he lived by his ambitions. 

2. What’s the best piece of advice you’ve ever been given?

Put yourself in his place and then analyze, if you were given a piece of advice about anything, it is certainly based on something you have done or people have seen something in you. The same goes for him, if you ask him about the best advice he has received, it shows how he was and what kind of thoughts people have about him. 

If you find him bragging about himself, he is not being honest with you.  


3. If you didn’t live where you currently live, and you could choose anywhere in the world, where would it be and why?

Choices regarding the place to live are another way of knowing about his personality. If he wants to live somewhere else and the reason is something relevant like his education or profession, it is certainly a good sign. And if the reason is irrelevant or just a thought of words he is certainly confused with his life. 

4. Who’s your role model? Who inspires you?

Idealization and role models are the best way to get the mindset of the person you are on a date. If his role models are people who have achieved in their life and he certainly looks forward to them, he is a dedicated person. 

Inspirations are another factor to look at. If he is inspired by self-made people and gets motivation from their struggles, he is a nice and dedicated guy, but if you find arrogant and selfish people in his inspiration list, it is certainly a red mark. 

5. Who’s your best friend, and what do you love about them?

Friend circle is what you certainly have to ask. Every man makes like-minded friends. When you ask him about his best friend and what you like about him, you will be seeking into his personality and what type of person he is. 

If his friend list has people, who are dedicated achievers and people who put up a fight with their struggles, he is a serious guy. 

6. What are you reading at the moment?

Ask him about his habits and when he mentions reading in it, ask him about the reading he is doing currently. People who love to read have a very unique taste in reading. They read based on their mode, if they are feeling romantic, they read accordingly, if depressed, they read accordingly, and if they are always seeking motivated, they go for other stuff.  Knowing his books will give you an idea of what type of person he is. 

7. What’s your favorite way to spend the weekend?

Ask him about his habit and how he loves to spend his free time. Try to match your habits accordingly, and you often think the same as he does. Try to know more about his interests and think about whether you can make it work or not. 

8. What do you do for fun?

Fun habits are often different from other habits. Before you disclose your fun activities, try to get an idea of what he is fond of and what he does for fun. If you find your fun activities the same as his or quite close to it, he might be a good partner for you. 

9. What was the last film you watched that moved you/made you laugh out loud/inspired you?


Movies are another way, like the books, to judge his modes and what type of person he is. Seek his interest in movies and what type of films he likes: romantic, thriller, adventure, action, or Sci-fi. 


10. Who has had the greatest influence on your life so far? (Parent/grandparent/schoolteacher/boss/colleague?)


Try to understand and know important people in his life and who he cares about the most. Usually, they are the one who has the most influence. This also reveals how much of a social person he is. Learn how much people influence him and who they are: family members, friends, teachers, or their workspace colleagues. 


11. What are the 5 things you couldn’t do without? (Not oxygen, water, world peace! They might be things you carry in your handbag/purse at all times!)


If you find a man carrying a bag full of his skin care products you might find him weird or a man who carries his books on an adventurous tour. Things a person carries show a lot about his personality so try to learn them as well. 


12. What’s your dream job if you’re not currently doing it?


A dream job is another thing that is connected to personality and ambitions. If he is currently doing it you will find him happy in his professional life. Certainly a good sign. Dream jobs are connected to dreams and what he looks forward to in his life. 

If you find it attractive and find a connection with his ambition, he is certainly a good man for you. 

13. Where do you go when you want to feel calm/happy/peaceful?

The place that makes a man calm and peaceful shows what he loves to do. If he feels peaceful in a library or feels calm in his gym, or if he feels calm around his friends, this shows a lot about his personality and what type of person he is. 


14. Tell me something about yourself that might surprise me.

If he is comfortable and interested in you, he will disclose some surprising things about himself and reveal everything about him. So try to dig him for that, but make sure you don’t look too desperate when asking about his secret; this might irritate most of the man. 

15. What’s the proudest moment in your life so far?

Their proudest moments are connected to ambitions and will show what kind of person he is. This is something you can easily ask and get the answer. So be precise and ask him about what makes him feel proud and other such things. 

16. If you had 24 hours to do whatever you liked in your city, what would you spend it doing?

Ask him about how much he knows about the city and what he likes to do in his city. A man who loves to socialize will not hesitate to answer this question. Try to make yourself comfortable with such a situation and ask yourself whether you will be fine doing all this stuff, if you are he might be the right person for you. 

17. What’s the most significant risk you’ve ever taken?

Men are risk-takers and they love to do things that involve risk. Ask and judge what type of man he is. If he is a risk taker ask yourself whether you are comfortable with such a person or not. 

Listen To Him As You Ask Him:

When you are asking him all these questions, make sure you give him plenty of room to make him comfortable and answer these questions. Moreover, he will be asking the same as you do, so feel comfortable while answering. 

One meeting might not be enough to judge someone, so go for more catch-ups and gossip to make your decision. 

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What To Expect On Your First Date & 17 Questions to Ask on a First Date

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