150 Interesting Questions – The Best List You Need

Interesting Questions

How awkward does it get when a conversation comes to a still? It's just like empty space with tight lips and almost dysfunctional brains. Now this situation is sprinkled with yet another monotonous question making it altogether declining. To overcome such situations, we have just the most fun questions to fuel your chit -chats whether you are talking to your crush, boyfriend or girlfriend. These questions do not follow one track but serve you with a buffet of questions for you to choose from. Even though the questions have been categorized yet they are highly flexible when it comes to mixing and matching them.

Probably we don't provide you with very heavy and deep questions but that is what the beauty of this platform is. We have a fresh take on the questions pertaining to the theme 'life' which will not really throw you into an analysis zone but keep you revived and sorted like a breath of fresh air.

Here's to getting away with real stinky questions on a date, casual meet or Instagram, scroll and see the categories:-


Interesting Questions To Ask on a Date


  • On a scale of 1 to 10, how much of a Joe Goldberg are you, basically your staking skills?


  • Tell me some of your successful stalking stories?


  • Have you ever felt like running away from a girl/ boy on a date?


  • Do you like traveling alone or with a group of friends?


  • Are you more of a Dog person or a cat person?


  • A guy /girl you would date at gunpoint?!


  • What should your ideal meal for a date be?


  • Honestly, do you prefer a pajama date or an all dressed date?


  • Choose-Fries or pancakes.


  • Who is your support system?


  • What was the last time you almost got a heart attack?


  • Ever said Drinks on me and then regretted?


  • Given an option between tasting different cuisines and going for normal pizza, burger meal (given you haven’t had these for more than 2 weeks ) what would you choose?


  • Have you ever felt like being part of any movie?


  • Are you a very competitive person?


  • Are you an Indie pop person?


  • Which song can make you go all dancing?


  • Would you rather apologize to someone or stand one entire day in the sun?


  • Is there a superhero in your life?


  • Do you have a funny story with your best friend?


  • Would you like to share cheesy pickup lines?


  • Have you ever had a friend with benefits?


  • What is the worst thing that you have done in your hangover?


Interesting Questions To Ask a Guy


  • Have you liked secretly any of your friend’s sister and stayed quiet about it to not spoil the relations?


  • Forget for a moment that you are in a relationship. Is there any girl you would like to spend time with to know her more because you feel the things might work out but either you are afraid or she is very unapproachable.


  • Have you ever thought of blogging or vlogging?


  • Do you prefer checks or plain t-shirts?


  • What do you notice first in a girl?


  • Have you ever felt like shouting at a friend whose activities you were unable to withstand but still resisted from doing so?


  • Do you want a girl good at managing things as your life partner or someone careless with whom you could have a lot of fun?


  • If you were a traveler, what would you have preferred between flights and train journeys?


  • What series could make you go all crazy and talking?


  • What seems okay, getting late for college or a date?


  • Have you ever kissed without brushing?


  • What kind of people intimidate you?


  • What will your baby girl’s name be?


  • Do you crave for sunrises or sunsets?


  • Do you have a dream destination?


  • In the company of what person does your stomach start hurting because of laughing?


  • Do you see any positives of Donald Trump’s rule?


  • What role are you usually made to do during Thanksgiving?


  • Who is the last person you texted?


  • What do you do in your free time?


  • Do current affairs interest you?


  • Ever had a paranormal experience?


  • If given a chance,  against whom would you take revenge?

Interesting Questions To Ask Your Crush


  • Have you ever been on a dating site?


  • Are you more inclined towards Rugby or Soccer?


  • What will your perfect date be like?


  • Do you prefer intimacy or cuddling?


  • Are you more of a movie person or a series person?


  • What is it that is completely unacceptable for you from your partner’s side?


  • Have you ever found anyone in your life like legit irritating?


  • Would you prefer bike rides or car rides in the countryside?


  • Do you like cooking?


  • Are you comfortable with surprises?


  • If dated any girl before, is there anyone you long to go back to on friendship terms or getting back together?


  • What filling will your subway have?


  • Choose-Gyms or Jogging.


  • What is the craziest thing you have done till now?


  • Do you believe in destiny's play?


  • From your first salary, for whom will you buy your first gift?


  • Is there any skill you would want to improve upon?


  • Have you ever been obsessed with a cartoon character?


  • Honestly, would you go out with your dog or attend a concert?


  • If you encounter a ghost, what will most likely happen to you?


  • Do you know what people think of you in the first instance?


  • When do you feel like you don’t belong to the crowd?


  • Do you ever find solace at religious places?


  • What has been your most funny Halloween costume?


  • Are you excited to meet new people?


  • What is your definition of a good spent vacation?


Interesting Questions To Ask Your Boyfriend


  • How much are you invested in this relationship, emotionally?


  • Have you ever had any ‘epic moments’ with her?


  • When do you legit find your girlfriend very attractive, it could be any activity of hers or anything that she wears?


  • Is it you who throws tantrums or your girlfriend?


  • Ever got attracted to your girlfriend’s friend?


  • Someone in your life who resembles some qualities from any of the characters from Brooklyn 99?


  • What movie genre would you watch at night with your girl?


  • What was your first job?


  • Are there any positive changes happening In your life?


  • Do you manage to tackle negativity or do you succumb to it?


  • Have you ever felt insecure about your body?


  • Post-retirement where would you want to settle and what would you want to do?


  • Would you rather do gaming with your girlfriend or watch a match with your friends?


  • What has been the sweetest gesture from your girlfriend?


  • Who is the last person you followed?


  • What should be the name of your Autobiography?


  • Do you believe in superstitions?


  • What is the weird thing that people don’t know about you?


Interesting Questions About Life


  • Are there any embarrassing moments that taught you something?


  • What is your ratio of isolation and socializing?


  • What do you do in your ‘Me Time’?


  • What is your priceless possession?


  • Choose-Knowledge or wisdom.


  • What has been your dejected phase of life from which you rose high and are happy that you are done with the episode or maybe you learned something from it?


  • What are the top five things in your bucket list?


  • If you had to change something about yourself, what will you?


  • Choose-Sitting and figuring out your life or having coffee/tea with a mountaintop view.


  • Were you ever forced into this career?


  • Was there a passion you wanted to take up as your profession.


  • How many times have you felt like tearing your French learning books?


  • If you ever had to start a business, what would it be?


  • Between image and money, what is more important?


  • Do you talk to yourself?


  • What is the concept of best friend for you?


  • What is your level of highest achievement?


  • Have you ever handled a stormy situation positively, something that you are still proud of?


Interesting Questions To Ask on Instagram


  • Who is the person you would want to meet for the first and last time? ( mention the names of 5 to 6 fictional or non-fictional characters  from which the person has to choose)


  • The one song that you will play in an open roof car while driving in a beautiful rural area?


  • What will your  Personal Diary’s cover say?


  • Are you a sweet tooth or a spice monger?


  • Choose- K pop or K drama.


  • As of now, does school score over College or vice versa?


  • Choose-A great quinceanera or a great wedding.


  • For your birthdays would you go for all pomp and show or is it about spending some time alone?


  • What is your favorite hangout spot?


  • Classics, fiction, non-fiction, what’s your preferred?


  • What country’s culture are you in love with?


  • Would you go for the classic white gown at your wedding or will you try something different?


  • Who is your spirit animal?


  • If you are asked to support PETA and leave non-veg, would you do it?


  • What is your go-to piece of clothing?


  • Are there any weird talents or habits that you possess?


Interesting Questions To Ask a Girl


  • Honestly, has their ever been a time when your friends have crossed the fine line between disrespecting and joking, making fun of your dressing?


  • How do you make yourself feel special?


  • What will your tattoo say?


  • A word that you use the most often?


  • How would your best lingerie look like from Victoria secret?


  • What is your go-to accessory or jewelry?


  • Stripes or Graffiti shirts?


  • Have you ever had a secret crush?


  • Are you afraid to tell your pocket money from the fear of being judged?


  • Choose- Hitchhiking or fully planned tour.


  • Should your wedding ring be a Claddagh or have precious stones?


  • If you had to give a theme to a cocktail party, what theme would it be?


  • If you had to write a message on the balloon and leave it in the air for it to sore high, what would the message be?


  • Who’s your woman crush in College?


  • Whose that one girl who fakes it out the most in College whether be boyfriends, clothing or anything?


  • Turn off incidents are epic, ever experienced one?


  • Choose- Close to Nature in North Carolina or hustle-bustle of New York.


  • Has any relationship severely affected you?


  • If you were asked to learn a language, which language would you try?


  • Are you a huge collector of international souvenirs?


  • Who was the last person who made you cry?


  • What is the first thing you notice in a man?


  • Where would you like to get your next piercing done?


  • If you happen to celebrate your 25th anniversary with your partner, what would you do?


  • Ever got popular in school because of a boy?


  • Which photo editing app do you use the most?


  • Have you ever dated a noob?

More Game and Questions:

Conversation Starters

First Date Questions

Ice Breaker Questions

First Date Questions

Deep Questions That Make You Think