Top 30 Dating Questions for That Mind Boggling First Date

Make your first date night easy with these top dating questions.

By Adina Mazilu
Top 30 Dating Questions for That Mind Boggling First Date

Going on a classic first date during these modern times that we live in can be one of the trickiest things that you can do in your life. If you come to think of it, it’s quite a paradox that finding your significant other has become this difficult when there are so many dating apps out there that are supposed to help you out. Well, this might happen because people have become so used to talking online that when there’s a real person in front of them, things become awkward. 

But what is a first date? The general definition might point towards a meeting between two people who are hoping to discover that the one sitting across the table shares the same interests and passions. Unfortunately, things are not always that easy. This is why in this article, we will be sharing some of the most important dating questions that you can ask during that mind-boggling first date that scares off so many of us. Here we go!

30 Good and Fun Dating Questions to Ask a Boy

From a girl’s point of view, asking the man you’re on a date with to share more about himself should not be that difficult. After all, that’s the reason why you are both there for! So, don’t be afraid to dig a little deeper and extract some answers that might interest you for a possible future relationship. As long as you don’t become too indiscreet or annoying, he should be fine to answer you some of these questions about himself: 

1. Where were you born?

This is interesting to know and one of the most basic things that a possible future partner should be aware of.

2. Did you go to school there?

Again, one of the most basic and fun questions to ask a guy on a first date. This usually creates a room for either party to further elaborate. 

3. What about high-school?

This is where it starts to get a little more personal as many guys want to avoid revealing what kind of person they were during high-school. He might not have been a straight-A student, might have started smoking during that time, or might have had lots and lots of girlfriends. He will probably not tell you everything, but it’s worth trying if you want to get to know him better.

4. Have you been to college?

This is a risky one because the guy might get the impression that you’re only interested in his education and therefore, salary. In fact, try to make him understand that you are simply curious about this part of his life and that is perfectly fine to skip going to college, especially if that’s what he wanted back then.

5. What’s your favorite movie/book, TV series?

This is a classic question that both genders can answer to. He doesn’t have to offer a clear answer, but it will be a perfect opportunity to start talking about what you do or don’t like in terms of TV, movies, and books. It will help you find some common ground and also differences between the two of you. If you notice that your tastes are completely different, it may be better to avoid going on a second date.

6. Where do you like to travel?

There are plenty to ask about this segment as it can divert out on where has he been to, what are his upcoming planned trips, what is his dream destination to questions such as is he an avid backpacker or a luxury travel person. Is he an adventure traveler or an explorer.

7. Who is your role model in life?

He may answer that his father or mother are his role models, and that’s perfectly fine. However, he might also have some more famous role models.

8. What are your hobbies and passions?

A guy who has no hobbies is not worth your time, trust us!

9. Do you like to have a good time?

Translation: do you go out often? It might be interesting to know this from the get-go.

10. What makes you laugh out loud?

11. What food you love/hate?

Many couples find common ground when it comes to food. It could be the food they hated the most or the ones they can't live without in an apocalypse. 

12. Do you have a long-term goal?

Remember: no goals, no interest!

13. Do you get along well with your family?

This can be crucial if you two become serious.

14. What kind of child you were?

The naughty type? The nice type? The quiet or the noisy type?

15. How’s your mother/father like?

Some guys do not feel comfortable to share too much on this on first dates and that's totally normal.

16. What do you like to do in your free time?

Linking it back to hobbies again. If the person likes to play games and stay at home all day long whereas you are an outdoorsy person who's interested in sports and going under the sun, this relationship will need some careful consideration.

17. What about weekends? How do you like spending them?

Translation: are you lazy when don’t have to work? Will we go out together during weekends?

18. Do you have a favorite place in the world?

This is another way of asking if he travels a lot.

19. What’s your favorite band? /Who’s your favorite artist?

20. What kind of music do you normally listen to?

21. Do you watch game shows or any other kinds of programmes?

22. Do you like cats or dogs?

His answer might determine the fate of your eventual relationship! Joke aside, this might be interesting to know.

23. Do you have a pet right now?

24. If you could eat one type of food for the rest of your life, what would it be?

25. Do you normally drink alcohol?

Make your date understand that there’s nothing wrong in having a drink from time to time as all people do. However, you want to know if he ever exaggerates or, on the contrary, if he doesn’t drink alcohol at all. 

26. What’s the last place you traveled to?

27. Do you have any pet peeves?

28. What about your sibling? Do you have any?

29. What would you do if you won $1 billion?

By asking him this you can find out whether or not he is the kind of man who spends a lot.

30. What would you do if you went broke?

Again, a way to find out whether or not he is the kind of guy who becomes desperate easily or if he is more rational than that.

30 Good and fun Dating Questions to ask a girl

When it comes to a guy wanting to find out some details about his possible future partner during a first date, things can get quite complicated. Not a lot of men have the courage to ask that many questions for fear that they would come across as annoying or stalkerish. However, the key to this problem is to know how to phrase these questions so that they don’t give off the impression that they have other meanings too. Here are some of the best questions that a boy can ask a girl during a first date!

1. Do you have a bucket list?

This question could offer you an insight into what are her hopes and dreams for the future and what she hopes to achieve.

2. Do you love your job?

Most people don’t so don’t judge her too harshly if she’s one of them.

3. Are you a morning person?

4. What’s your favorite food in the world?

5. What’s your favorite thing to drink? Alcoholic or not?

This is not like asking her if she’s an alcoholic. It’s more of an indication of what kind of party person she is.

6. Do you like to cook in your spare time?

Maybe you two could cook together?

7. Do you like giving people gifts?

8. What’s the best gift that you ever received and from whom?

Maybe from an ex-boyfriend?

9. If you could meet anyone, dead or alive, who would that person be?

10. Do you like going on dates?

11. What’s something that you have always wanted to try?

12. How proud are you of your achievements until now?

13. What’s something that you are very good/very bad at?

14. What’s your favorite childhood memory?

15. What about your favorite holiday?

16. Do you have a favorite family member? Who is it?

17. Do you want to have kids someday?

This will offer her a hint that you might be ready to invest in a serious relationship.

18. Do you usually save money?

19. What’s your favorite color to wear?

20. Do you usually set New Year’s resolutions?

21. Do you like to plan ahead or be spontaneous?

22. What’s something that you would never do in life?

23. What’s your dream job?

24. Do you watch sports?

Most women don’t watch sports but might pretend to like a team just to make you happy. Don’t invest too much thought into this question.

25. What’s something that you hate/love in a person?

26. Do you have many friends?

27. Who is your best friend?

28. What’s the best piece of advice that you ever received?

29. Do you like to help the unfortunate?

30. What do you feel most grateful for?

Top 10 Online Dating Questions to ask both genders

1. Do you usually like to meet possible partners online or offline?

2. What made you go down this route?

3. What did you like about my profile?

4. What brings you to this particular online platform?

5. What would your dream life look like?

6. How do you like to spend your weekends?

7. What’s the most important thing in your life right now?

8. What are your hobbies?

9. Is money important to you?

10. Would you agree to meet face to face?


All in all, it appears that going on a date for the first time is no easy job, regardless if you’re a boy or a girl. It’s equally difficult to try and find out more about your possible future partner. This is why the aforementioned questions might give you a hint on how to approach that mind-boggling first date so that the person you’re meeting gets the right impression about you and about your intentions.


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