40 Questions to Ask a Guy on a First Date

By on October 2, 2014
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In the modern world, a first date is not always a meeting with someone you know well or have even met before. It has strangely become acceptable to meet up with a perfect stranger at a random cafe and chat. Sometimes, this works out extremely well, but it doesn’t always end for the best. If you want to take some of the sting out of the first date, make sure to ask the following questions. Before things go to the next level, you need to make sure that you are a good match for your date.

Before You Go


These questions are important and will make sure (hopefully) that you do not go home with a serial killer. Although bringing them up is important, you may frighten off your date if you read them from memory. Before your date, make sure that you have a rough idea of the most important questions. During the date, throw these questions naturally into the conversation. You can always use these questions when it is difficult for your date to open up on your own. If a different question feels more natural for you, feel free to switch things up.

First Meeting with Girl on Dinner

To prepare for your first date, try these questions out:


1. What do your parents do for a living?


It may not be the best first question to ask, but this question can certainly reveal a lot about his family life. While he answers, read between the eyes. From his response, you will be able to see how comfortable he is with talking about his family. You’ll also get a glimpse into what growing up in his household was like.


2. What is the best gift you have ever received?


Learn more about his interests and his interpersonal relationships.


3. How many siblings do you have?


Sometimes, all it takes is a simple first question to open up the conversation to other topics. A question about his siblings can lead to other family-related topics or interesting stories from his childhood.


4. Are a morning person or do you prefer being a late night owl?

night life

Asking this question can reveal his lifestyle habits as well as his general sleep schedule. This is a sneaky way to see if he parties the night away or plays video games to the wee hours.


5. Who is your greatest role model?

steve jobs

The person that he looks up to says a great deal about who he is as a person now and who he aspires to become in the future.


6. What are the top two items on your bucket list?


This question can open up a conversation about the dreams that you both share and life goals.


7. What are some of your nicknames?


His nicknames can reveal interesting stories, relationships with friends and the things that he cares about.


8. Have you ever actually followed through with your New Year’s resolution?


Although most people make New Year’s resolutions, few people end up actually following through on them. If he is like most people, you can also ask what the resolution was supposed to be originally.


9. What do you normally drink?

first date

If you at a bar of some sort, you can always ask what he normally drinks. His typical drinks reveals a great deal about his personal tastes.


10. What thing you would change in the past if you could take back some of the information that you know now?


Would he change something he regrets or play the lottery? Whatever his answer is will reveal a great deal about who your date is as a person.


11. How was your day? What did you do today?

start convo

It may be typical, but it is actually one of the best ways to see what his normal life is like.


12. Did you have a better relationship with your mother or your father when you were growing up?

his family

Asking about his family reveals the type of person he is and his ability to form close bonds with other people.


13. What is your favorite vacation spot?


You don’t need to start planning a joint vacation now, but understanding the places he likes to travel to could provide some insight on shared interests.


14. If you could rule the world, what would you do?

rules the world

Silly or unrealistic questions can still be an enjoyable part of your date.


15. What quality in a woman turns you off?


Typical answers typically include someone’s face, voice or personality.


16. What quality in a woman would make a relationship impossible?


Before you take this any farther, you need to know the answer. Major issues can be prevented if you find out in advance that he hates cats or wants a stay-at-home wife someday.


17. What kind of movie do you like to watch?

Warm-Bodies_top romantic movies

When it comes to movies, it is always interesting to find out what someone else is interested in.


18. What is your favorite restaurant/food/music?

romantic restaurant

All of these types of questions help you figure out more about who he is and how compatible you guys will be as a couple.


19. What do you do after work is over with?


This is a great way to see if he likes to cuddle and stay at home or if he likes to go rock climbing or party in his off-hours. No matter what his hobbies are, you will want to make sure that his interests match up with yours.


20. Where do you work?


After asking this question, you should always follow up with a “why” question. Why does he work there? Why did he choose this profession? These questions can indicate what he feels passionate about in life. If he is not at his ideal job, ask him what he wishes that he could do for a living.

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