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18 Questions to ask a guy on a first date

1. How is your week going so far?

Such an innocent question. You would ask it no matter what, right? So why would I put it on the list then? Everyone knows that on the first date he’ll be asked many questions, and there’s nothing wrong in that. However, people are not always honest about their lives. But if you ask your questions at the very beginning, before you sit down for the dinner or coffee, it’ll sound more than normal, just a starter of a chat.

Also, the way he sees his regular week is the way he sees his life. 

The answer will tell you if he has a positive personality or positivity is not part of his Monday to Friday routine. 

2. When was the last time you had really good fun?

Why would you ask that? We all see “fun” as different activities. For you, this could be a night out with friends and lots of alcohol, and for him, this could be a day out, hiking. Defining what’s “fun” for the other will point you if “your fun” fits his.

3. Do you love what you do?

Why? You don’t have to be a scientist to know that people that do what they love are happier than people that hate what they do. They are positive, fun to be around, supportive and loving. If he doesn’t love what he does, the next question will get you to the next level.

4. What is the work of your dreams?

Why? You won’t find a happy person who doesn’t work towards his dreams.

Unless his idea is to live on Mars, I don’t think there are many other reasons not to pursue what he wants in life. If he dreams to work something different than what he already does, then ask him what his plan to achieve it is. Not everyone is blessed doing what they love. However, constantly walking towards our dreams is a choice.

Need proof?

Dating him or anyone else is an example of you pursuing the dream to create a healthy fulfiling relationship with someone who appreciates you. Am I right or am I right?

5. What is your first childhood memory?

Why would you ask that? Our first memory defines our biggest fears or our biggest values. My first childhood memory is the moment when my parents split up, and I had to leave my mother’s place so I could go to live with my father. You see, that shows fear of abandonment I fight almost all of my life. The things that shake us during our first years of life say a lot about us today.

6. Do you have a family tradition you loved back in the days and would like to implement in your family one day?

This question will show you what his values about family are, what his perfect image of a family is. The important things to him in the past would be important in his future too.

7. If you had to chose to live anywhere in the world, where would that be?

Even if it sounds like an ordinary, cheesy question, this one will tell you not only where he wants to live if he had a choice.

Nowadays, we have the option to live anywhere we want in the world. Even for you, my dear, if you want to live in Spain, but you’re somewhere in Australia, make plans and move. It’s not as easy as I tell you, right? If we are not happy where we are, and our hearts tell us to go somewhere else, it’s because something’s waiting for us there.

8. How would a perfect day look like for you?

Another simple question to ask a guy on a first date. Your perfect days might not match, but your dreams of perfection should be at least similar.

9. What annoys you the most about your life?

A little tricky question to ask him on a first date, be sure you’re comfortable with each other before approaching the subject.

However, it’s another chance to see if he has a positive vision of his life. The things that annoy us could be something small and funny, or something important we fight with. How he sees those annoying things is the way he sees the negative part of life. Is he getting frustrated while talking? Or he just prefers to not to think about what bothers him? Useful information for you and there’s no right answer to that.

10. What is the thing you would never compromise with in life?

It’s not about relationships; it’s about life. All those questions to ask a guy on a first date are meant to give you a few glimpses of his inner self. You have things you would never compromise with as well. Well, what a better time to find out his. He will ask you the same, I’m sure, so be clear about yours.

11. What are the things you would never compromise within a relationship?

Your heart was broken.

Probably more than once.

Ask for the things he would never compromise within a relationship and if he asks you back, don’t be afraid to share the information.

12. What are the things about your life you’re the proudest of?

Did he overthink before answering that one?

Is it hard for him to pick one thing or it’s hard to find at least one?

Is he happy with something material he bought, or with a place he visited?

Or maybe proud of something he created by himself? It could be something he did for others…

This is one of the most important questions to ask a guy on a first date. The things we are proud of, we want to repeat. How bright his future is, depends on what he’s proud of.

13. What is the worst first date you’ve ever been on?

One of the tricky questions to ask a guy on a first date, and it’s up to you how you see the answer. Having fun with ridiculous dates is something you should probably save for later in the relationship. If he’s opened to discuss other people’s embarrassing moments on a first date with you, maybe he’s not so respectful as he should be. You wouldn’t want someone to share details from your first dates in the past, so why not to expect the same?

14. How many social media platforms do you use?

Why should you ask that? Seems innocent question but if you’re not a social media person and he uses at least seven platforms, at some point, you’ll feel you share him on Facebook. On the other hand, if you’re both in love with Instagram and SnapChat, that’s the modern image of a perfect relationship nowadays.

15. What was the last thing that melted your heart?

Ok, cheesy question, but it’s an excellent starter for sharing something that impressed him. What touches his heart is vital if you want to touch it as well.

16. What is your favorite weekend activity and how often do you do it?

It’s a perfect question to compare your favorite things to do during the weekends. However, just because your date loves skydiving it doesn’t mean he does it every weekend, so relax if you prefer to spend the day under a blanket. But, his favorite weekend activity could be two packs of beer and football games from Friday afternoon up till Sunday evening, and this is hardly something you could enjoy watching every weekend.

17. What was the hardest decision you’ve ever made?

Soul touching question to ask a guy on a first date. If he feels comfortable with you, he will share it. However, if he’s not into answering that one, you could share your experience without forcing him to do the same. He will most likely change his decision before the end of the evening.

18. What was the most important thing that happened in your life for the last six months?

… except for the fact, he met you, but you don’t have to say that ;). It matters to know what’s his life direction. If nothing has changed for the last half year of his life, probably he’s happy with his life. But if he already gave the impression he’s not so happy, then he had at least six months to change it. Chances are – he won’t change anything for the next six as well.

Find Love! Hold Love! Be Love!

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