21 Questions from Various Categories to Ask a Boy

Going for a date tonight and need help making conversation? Check out our list of 21 questions to ask a boy, while you’re on a date and getting to know him.

We all know about the ever-popular car game, Twenty Questions. However, that’s not what we are going to play here. We are discussing the topic on getting to know a guy you just met. First couple of dates are always tough. The pressure where you want to get to the other person is so high, that you can sometimes blurt out wrong things. You are interested in him and wish to know more about him as a person, while dating. Obviously, as the number of your dates keep increasing, both of you will definitely get to know one another with personal and intimate conversation. Although, if no one asks the right questions, how is it possible to get to know someone?

To help solve your dilemma, we have come up with interesting and good questions to ask a boy you like. We have collected different types of questions to ask a boy you just met, as they might help you into understanding who he really is. I know what you’re going to say; how can you really know someone by asking just 21 questions? There is no special magic in that particular number, because the more questions you ask, the better it will be for your relationship. When you get to know someone for who they really are, it makes being with that person a lot easier. So if you are going on a date and wish to keep a steady flow of conversation going, without the awkward silences, then here is a list of 21 questions to break the ice between the two of you, and aid his reluctance to talk as well.

Questions You Should Have Answers To

The concept of these questions is quite simple. But remember, don’t think of them as standard guidelines. Instead, think of these questions as a fun way to get to know him. The list is divided into three separate sections with each of them containing questions. You can choose these questions according to the kind of date both of you are on, and how comfortable each of you are in talking over them. You can even mold these questions and add a few minor details of your own. This way, you are not only the one answering the questions, but showing him a part of you as well.

General Questions

Do you have a favorite Halloween costume? If yes, then why?
Have you ever been in any embarrassing situation in your life? What was it?
Do you have any favorite childhood memories?
Are you an only child? If not, how close are you to your brother/sister?
Whom do you like better – Bob Ross or Mister Rogers?
If God gave you one wish, what would you ask for?
Tell me something about your best friend.
Is there any event in your life or scene from the movie which made you laugh the hardest?
Do you love a movie which everyone else hates, or vice versa?
Do you have a favorite fragrance, something from your past, which brings back happy memories?
If you were a server at some restaurant and a customer was rude to you, would you spit in his/her food? Why?
Let’s say you’re planning a nice dinner party but could only invite 3 people, who would you invite and why?
If you got the power of invisibility, where would you want to go and/or what would you wish to do?
Do you like to read (listen to music, play video games, watch television)? If yes, then what kind of books do you own? Why?
If your life, spontaneously, changed into a movie, which movie and/or actor would like it to be?
You are a scriptwriter and have to come up with a new show. And your time starts now.
What is the cheesy, fattest fat-filled, calories-filled food you like to hog on?
If you were given the power to get rid of one state, which would it be? Why?
Is there a song (which you know is the most embarrassing song ever) you know all the words to and sometimes sing (when alone)?
Do you and your parents have a favorite place for dinner or any kind of celebration?
Did you love or hate school? Do you have any fond or bad memories about school?

Personal Questions

What do you consider as your deepest regret?
What do you like about me/my habits/my features?
What’s the furthest you’ve gone in a relationship? How long/serious was it?
Do you remember your very first date? What was it like?
If you don’t like a person, how do you handle him/her?
Pick one. Smart, ugly/dumb, and beautiful. Who will you like to be?
Is there any instance in your life that has made you think about death or dying?
Suppose you won the big lotto tomorrow (a million dollars). What will do with all that money?
What is the worst lie you’ve told your parents? Did they ever catch you?
Do you miss or think about your ex? Check his body language to see if he’s telling the truth.
Have you ever dated someone from a different race or culture? If no, would you ever?
What’s the biggest issue/problem with our world in today’s time?
Do you think people are doing anything constructive about changing our world for the better?
If you could meet or have lunch with anyone, dead or living, who would you pick? Why?
Who’s your favorite actor or actress? Tell me something you like about him or her?
Let’s say, I asked you to cook something romantic for me. Will you? What will you make?
Which is your favorite time of the year? What would you do on a Spring/Winter/Fall/Summer day?
You woke up one day and found that you’ve turned into a woman. How will you react?
Are you currently working on some big plan or goal? In life or work? If he says “you”, give him bonus points for that.
If you can pick a profession or hobby to do for the rest of your life, what will it be?
Do you enjoy, support, or have you ever done any kind of drugs? How do you feel about that?

Intimate Questions

Give me your 5 turn ons and turn offs.
Did a girl/girlfriend ever break your heart? What happened?
Which place will you choose for our first kiss? If you guys haven’t kissed yet.
Have you ever cheated on your girlfriend? If yes, did she catch you?
Did your girlfriend cheat on you? If yes, did you catch her?
Tell me one thing about you that you find the sexiest.
Tell me one thing about me that you find the sexiest.
Do you believe in God or the concept of God? Yes or no, why?
Do you have any fantasy which no one knows about? Will you tell me?
Do you like kids? Eventually, how many kids you think you wish to have?
Do you think “happily ever after” exists? Or that something only girls believe in.
Have you ever been in love before? If yes, what do you remember of it?
After me, who do you consider your best or closest female friend?
Suppose I had an accident and was left with horrible scars (on my face and/or body) for the rest of my life, would you still love me?
If a celebrity you liked asked you to be with her, would you leave me?
Suppose I was dating another guy while being in a relationship with you, how will you react to that news?
Do you plan to get married in the future? If yes, how old do you think you’d be?
Is there something about me that you don’t like or appreciate?
If a doctor told me I had a dangerous/deadly disease, would you leave me? Would you still love me?
Suppose I had to move away from here and that too for few years, would you wait for me or break up with me?
If we had kids, one of whom had health issues, how will you handle such a situation?

These fun questions are intended to work for different stages in a relationship. Some of these questions may seem tough for your guy. So, make sure you understand him a little before moving to the more “intimate questions” mentioned above. See what his responses are; try not to guess what he might say or what he should say for any questions. Let him give you an honest reply, because that’s the idea behind all of this. Have fun on your date and do let us know how it went!