Random questions to get conversation started

Random questions to get conversation started

Random questions are prompts to use to start a conversation. The purpose is the get to know someone. Here are 50 random questions to get the conversation started with anyone.

Remember how it feels to have a crush. Especially that nerve-racking situation when you want to talk to them but can't do it because it's just so hard to come up with something to ask them. Not only that but we also become so insecure thinking about questioning some odd questions out of nervousness leading to an awkward moment between you two. Do you feel the same? Do you even want to talk to your crush or ask questions that are not weird and good enough to get closer to them? Then my friend you are in the perfect place. It is important to ask questions which are interesting and easy to answer. You can even impress your crush by simply asking the right question to them at the right time and in the right place. But it could be a little tricky to know what to ask and when. So, we have listed these 60 random questions to ask your crush. We have also divided the questions into categories so that it is easier for you to ask random questions according to your taste and situations.

Random Questions: Simple

Simple questions are nice and light. These questions need not be a big of a brainstorm. These kinds of questions are comfortable and easy to answer. It does not make you look like you are trying too hard. Simple random questions are good to start with, it not only helps in knowing them a little more but also brings you guys closer. These are icebreaker questions. Questions can include the various sectors of one's life. You can ask her/him about their family, interest, hobbies, preferences, and so on. Make sure the questions need to be light and not too deep.


1. What do you like doing in your spare time?

2. Do you like to play any instruments?

3. Do you play any sports?

4. Which are your favorite sports?

5. Have you watched any mind-blowing movies recently?

6. What kind of genre of songs and movies do you prefer?

7. Do you listen to any type of podcast?

8. Did you hear that new song by [name of the singer and song]? It's so nice, I loved it. Did you?

9. Do you like traveling?

10. When was the first time you went somewhere far and nobody even knew about it?

11. Do you ever want to travel alone?

12. Which was the last place you went on a trip?

13. So, how many family members are you?

14. Do you live with your grannies?

15. How many siblings do you have?

16. Do you live with your parents or alone?

17. What is your favorite color?

18. What is your view on the seasons?

19. Are you a dog person or a cat person?

20. Do you prefer bike rides or car rides?

Random Questions: Deep

Deep random questions are the ones you can ask your crush after you clear the first phase. After questions, those simple random questions, and getting their answer back you already might have known them a little bit better. It is natural for your crush to ask you the same type of simple random questions. This way there is a chance that both of you have comfort with each other and are close enough to ask and know each other a little deeper. Deep random questions need not be too private but it is okay if you ask them about some stories of their life they want to share. Make sure not to force them to tell you everything, it is okay if they don't want to. Give them time and they will open up one day.


1. How close are you to your parents?

2. When did your parents be the proudest of you?

3. Have you ever disappointed your parents?

4. Have you ever been disappointed by your family?

5. Have you ever faced any traumatic situation in your life?

6. What do you think, what happens to us after we die?

7. What if the world is going to end in a month? What would you do?

8. When was the happiest moment of your life?

9. What is your relationship status?

10. Do you believe in love at first sight?

11. Why did you break up with your ex?

12. Have you been into a toxic relationship?

13. What is your biggest fear?

14. If you could go back in time, what would you change?

15. If you could be anything or anyone, what would it be?

16. When did you cry the most?

17. Whom do you share everything with?

18. What if you win the jackpot, tonight?

19. Do you ever want to go somewhere far away? Just because you are so tired with these regulars?

20. Have you ever suppressed your feelings so that others don't feel bad?

Random Questions: Flirty

You asked them the simplest questions to come close to them and know them more, which happened. You then asked them the deep random questions which went right and become best buddies but you did everything just to become a friend or to make your crush start thinking about you? Flirting is the most crucial part if you want them to accept you the way you want them to. It can be a little awkward to suddenly start flirting with them. But the ones mentioned below are the ones you can use anytime and need not be a part of any steps. Remember flirting does not mean to be cheesy but to impress them with your humor and witty questions or responses.


1. Aren't you too good to be single?

2. How could you be so good at anything?

3. How did you get that job? It's so impressive.

4. What are you looking for in a guy/girl?

5. Are you free tomorrow? I had these two tickets for the movie.

6. Were you always so funny? I loved it.

7. What is the naughtiest thing you've ever done?

8. Have you ever snuck someone in at your house in the nighttime?

9. I wanted to experience how it feels to sneak out at night. Would you give me company?

10. There is a new fancy restaurant, would you like to have dinner tonight?

11. How do you manage to look so attractive every day?

12. What do you like to do on your first date?

13. What kind of guy/girl attracts you the most?

14. What would you do if you accidentally encountered me naked?

15. What if I ask you for a date?

16. What was my first impression of you?

17. Was I ever a little more than a friend to you?

18. Which do you prefer the most hugs or kisses?

19. What is your biggest turn-on?

20. What is your biggest turn-off?

So, these were the 60 random questions you can ask your crush. There are many more, the list never stops. It is advisable to ask your crush questions which initiates conversation and keeps it going. Do try hard or ask questions as if you are interviewing them. There is no need to be nervous as you are just talking to him/her and getting to know them better.

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