190 Best Personal Questions To Ask – Girlfriend, Boyfriend, Someone, Guy and Girl

deep personal questions

It is often understood that the way a person answers can reveal much more about his personality. Their thoughts, views, understandings, and upbringings are all reflected in the way they speak and answer. So if you’re a person willing to understand a stranger or a girlfriend willing to know more about her man, you can here try out some ways to question them. These questions have been crafted out carefully and with care so that based on the relevant situations in your life, you can proceed with the questions!

So go ahead and ask all the questions to your heart's content from the selected 190 questions handcrafted for our readers!


Personal questions to ask

Personal questions To Ask


  • If I tell you that you were to die tomorrow, what is one last thing you would do?


  • Can you dive into a pull full of sharks if someone can reward you with one million dollars?


  • Did you ever pretend to be someone that you were actually not, just because others liked you with your fake mask?


  • Were you jealous of your sibling’s achievement ever and thought that you were a loser in your family?


  • Did you ever feel like walking out of your house just because the pressure and expectations from your house members were too much to handle?


  • Can you ever think of being a stripper over a renowned profession?


  • Did you ever feel like cheating on your partner just because things weren't good enough to keep the spark?


  • Has it ever occurred to you that you are not at all useful to your friends and they might dump you? What would you do?


  • What was the mischievous thing you always wanted to do but due to your reputation, you restricted your actions?


  • Have you ever drunk-called a person you had never thought of? What did you say to him?


  • Did you ever have bad intentions about someone for absolutely no reason?


  • Have you ever spent a lot of money to buy something useless and were afraid to say it to your parents?


  • Do you feel asking someone for something is easy and should be done often?


  • Has someone ever asked you for a favor and you have not completed it till today?


  • Did you ever break a promise you made to someone and did not feel guilty at all? What was the promise?


  • Did you ever do substance abuse and went to attend the high school right after that?


  • Have you deliberately kissed someone by pretending you were drunk and enjoyed it?


  • What is the one thing you always wanted to say but you could not? Now you can!


  • Can you give up on all the relations you had till now if you got a chance to be immortal?


  • What will you do if you’re trapped in a room full of the creatures that you’re scared of?


  • Did you ever regret that your and your parent’s thoughts didn’t align?


  • Can you ever forgive someone who has hurt you and changed you to the core?


  • Do you believe in venting out your anger immediately or you prefer to wait for revenge?


  • How firm are you about karma? Any personal experience to share?


  • Are you scared of dying? If yes then how do you feel you should not die?


Download the list of personal questions to ask below

Personal questions To Ask- questions list


Deep personal questions to ask a guy

Deep personal questions to ask a guy


  • Have you ever given a thought on watching a porn clip with your family?


  • Would you ever suggest the friends with benefits concept to your children?


  • Would you rather prefer heavy addiction or death? 


  • Have you ever done substance abuse while every family member is present in the house?


  • Have you got drunk so bad that you had a fling with a girl at the bar?


  • Can you agree if your girl says to live separately from your parents after the wedding? 


  • Do you feel that ‘bro’s before hoes’ is the ideal theme for your friends? Why is that so?


  • Have you ever fantasized about a person with the same gender as yours? When did that happen?


  • Do you feel like flirting with a girl and her best friend at the same time? How will you convince them?


  • Do you ever feel depressed about the fact that everyone expects you to outperform if you are the future head of the family?


  • Did you ever convince or begged a girl to unblock you after she blocked you?


  • Have you ever sneaked into your girlfriend’s room and successfully escaped?


  • Have you ever forced someone to do something that wasn’t morally right?


  • How old were you when you discovered the explicit content?


  • What are your life’s thoughts and ambitions that you think are very different from the world?


  • Being a guy, have you ever cried in front of the people because your heart was heavy?


  • Do you ever feel like giving up on a job and converting into a house-husband?


  • Have you ever met with an accident and pretended to cover it up because you didn’t want to get scolded?


  • Have you ever mistaken lust for someone as love and then realized it later?


  • Were you involved in a fight so bad that the police had to be involved in it?


  • Would you ever step into your family’s professional legacy just because of the reputation of your family?


  • Have you ever faced the trauma of being body-shamed? How did you react to it?


  • Do you believe in working hard your whole life or gaining instant success by shortcuts?


  • Where do you think your date night will be spent the best?


  • Have you ever beaten up someone because he was trying to flirt with your love?


Download the list of deep personal questions to ask a guy below

Deep personal questions to ask a guy - Questions list

Overly personal questions

Overly personal questions


  • Are you an atheist or a believer, is there anyone who can affect your beliefs?


  • How do you feel when someone talks bad about you behind your back after they have left you?


  • Have you ever accidentally shouted cuss words in front of your family and regretted it?


  • Have you ever shared a secret to someone and they’ve broken your trust in that? What did you do after that?


  • Should sexual talks be made a part of family discussions so that the kids can be made aware of it?


  • What level of fake innocence have you shown in order to make a good impression in front of others?


  • If you are forced to give up on any one of your guilty pleasures, which one would it be?


  • Which out of the two is the friendliest place for a teenager – the bathroom or the bedroom?


  • Have your relatives ever walked in while you’re watching porn? How did you make up for it?


  • Should the explicit commercials be watched with families to improve its awareness and create open environments?


  • Have you ever tried to seduce someone with all your might?


  • Can you hold control over your emotions just because people don’t deserve to understand it?


  • Did you ever laugh in a serious situation and then realized that you blew it?


  • Have you ever forgotten your loved one’s birthday, realized it and yet did nothing?


  • Would you value religion over love or will you take a stand against it?


  • Did the thought of leaving your job ever occur to you but you dumped it because of the responsibilities you have on your shoulders?


  • Did the mask you always put on in public unknowingly replaced your original personality?


  • Has money ever blurred your definition of right and wrong?


  • Did you ever lose sight of your goals due to the day to day hustle of survival?


  • Have you ever tried to suppress your inner thoughts by surrounding yourself with too much noise?


  • Have you ever tried using an ouija board? How did it feel?


  • Can you ever consider being in a relationship with a person who is not of your class and status?


  • Compromising with your principles for doing something that is very important for you? What will you choose?


  • Ever had a kinky feeling to do something sexual via video calling?


  • If your girlfriend told you that she’s going to have your child, how will you react to it?


Download the list of overly personal questions below

Overly personal questions - Questions list

Personal questions about me

Personal questions about me


  • Do you feel that I would ever cheat on my love? 


  • If I were a guest at your place and I disliked your hospitality. How would you convince me to revisit you?


  • What do you think suits me more – anger or love? 


  • Which one quality of mine reflects out handsomely, when in public? 


  • What kind of vibes do you feel when I’m around?


  • Which are the top three flaws in my behavior?


  • What might be my taste of music? Does it go with my character?


  • Do I stand out in a traditional classic attire or in a modern funky design?


  • Do you think that I would ever play a fraud or a scam with the mere target of earning name and fame?


  • Shall I give up on my sincere and caring attitude and follow the ‘Tit for Tat’ policy against my foes? 


  • What would you be more interested in knowing about me: the past or the future?


  • Which is the biggest disadvantage of me being a teenager according to you?


  • Which person in my contact list deserves being hit badly in public?


  • Which dream would you like to live with me before resting on the death bed?


  • Which quality of me would you like others to imbibe and celebrate?


  • What do you think I’ll choose- royal life or the wanderer’s life?


  • How did you feel when I was in my lowest phase and had shut down everyone from my life?


  • Can you rate my character based on my behaviour and attitude towards you?


  • What is the darkest trait that you know about me and you haven’t told others?


  • Can you figure out who I’m secretly in love with?


  • If you were to ever set me up with a girl, then who would it be?


  • Can you ever count on me when you are stuck in your problems?


  • If I am to die tomorrow, what will be your last words for me?


  • How will my reaction be if I find out that my blind date is you?


  • Which music will I put on when I am feeling the happiest?


Download the list of personal questions about me below

Personal questions about me - Download the list


Personal questions to ask a girl

Personal questions to ask a girl


  • How would you react after knowing that there are many other women who misuse the laws and defame innocent men out there?


  • What matters to you the most while dating- money, looks, attitude, or physical love?


  • What do you need more- a limited real-time friend's circle or loads of social media followers?


  • Did you ever feel like doing kinky talks with a stranger out of loneliness if you got a chance to go anonymous?


  • How would you like to describe your menstrual experience every month?


  • How good of a character do you have? What will you do to improve a bad character?


  • What would you say to a girl that was molested but keeps mum because of the society's impression of her?


  • What is the highest and most important expectation that you have from your lover?


  • Would you take a bullet on yourself if it means you can save your in-laws?


  • How do you feel your ideal life after the wedding should be?


  • When almost every girl complains that all guys are the same, what do you think they have in common?


  • What according to you is a better option considering women’s safety – A black pepper spray or physical fitness training? And why?


  • Is there any characteristic male feature that you wish you could own? 


  • What according to you is a better approach – Modern open-minded way of thought or orthodox belief system?


  • Would you like to have a baby and raise it sacrificing your job or would you rather happily continue with your job?


  • “Women should refrain from drinking and smoking”. What’s your say on this?


  • Is it necessary for every guy to know the basics of homely activities like cooking, cleaning and washing clothes?


  • Why is shopping an obsession of every other female? Is it yours as well?


  • How strongly does a life partner’s support matter a female's growth?


  • Have you ever cut out your close ones from your life for no reason? Who were they?


  • Have you ever faked having period cramps to get more pampering?


  • How much importance do you give to your mood swings over rational decisions?


  • Are you an extravagant person or you believe in being economic and saving?


  • What would be your favourite yet public place for making out?


  • Do you believe in spending tons of money on cosmetics or you prefer natural beauty and looks?


Download the list of personal questions to ask a girl below

Personal questions to ask a girl - Download the list


Personal questions to get to know someone

Personal questions to get to know someone


  • How much do you think your inner peace matters to you over the money you're earning?


  • What would you do if you realize that your closest friend has kept you as an option?


  • If you ever realize that you are being cheated by your lover, what would be the first thing that you would do?


  • What would you do if you are given the chance of becoming the opposite gender for a day?


  • Would you be fit and sacrifice the food or you will eat to your heart’s content?


  • Will you prefer being sober or being drunk to express your deep feelings?


  • What was your weirdest thought while being in the shower?


  • Do you believe in being violent and fighting for your rights or do you prefer a nonviolent approach?


  • Which one of your weaknesses would you like to convert into your strength?


  • Would you rather beg for love or stay happy with self-respect?


  • If given a chance, which historic event would you like to change?


  • What according to you is the most important asset in life?


  • Which person would you like to receive a gift from?


  • Are you an atheist or a believer, have you somehow affected your beliefs?


  • Have your insecurities ever stopped from doing something morally right?


  • Do you ever feel that having good upbringings in the bad world has cost you a lot?


  • Has it ever occured to you that the education and hours of effort in high school was no good for you?


  • Were you ever forced to do something because it made others happy while you were crying inside?


  • Did you ever try to steal money from someone because your pocket money just wasn’t enough?


  • Have you tried to self-harm yourself because you were heartbroken?


  • Finding tonnes of gold or meeting a parted friend, what would be a better dream for you?


  • Which of your favourite things could you sacrifice for the sake of saving some strangers' lives?


  • Do materialistic goals have a place in your life?


  • What kind of a friend would you prefer- a straight forward personality or a cosmetically approaching one?


  • Do you believe in hiding your griefs so that your loved ones don't worry about your present?


Download the list of personal questions to get to know someone below

Personal questions to get to know someone - Download the list


Personal questions to ask your boyfriend

Personal questions to ask your boyfriend


  • Did you ever cheat on your girl because she was not keeping you happy?


  • Do you feel that most of the girls tend to empty your wallet?


  • If your girls disagree to be in a joint family after the wedding, then what would you do?


  • How will you convince your girl to make her agree to your terms?


  • What will you do if your girl's ex-boyfriend is back in her life?


  • Have you ever regretted being in a relationship with your girl?


  • Have you ever judged your girl's family members or passed comments on them?


  • Have you ever checked out on other girls just while being in a relationship?


  • Will you still accept your girlfriend if she has cheated on you?


  • Did you ever feel like you're falling for your girl's sister while dating your girlfriend? 


  • Have you ever tried to scare your girlfriend while she’s asleep?


  • Are you serious about marrying your girlfriend? If yes, then when are you proposing to her?


  • Have you tried to impress your girlfriend by lying to her and covering up your true self?


  • Are there any weird habits of your girlfriend that you haven’t told to anyone? 


  • Who is more dominating in your relationship- you or your girl?


  • As a boyfriend, do you feel that you deserve your girl correctly?


  • Your play station or your girl?


  • Who is your greater priority?


  • Have you ever taken up any household chores to impress your girlfriend?


  • Will you ever consider dating a girl that is not good-looking but with a pure heart?


  • Did you for once, compared your ex and current girlfriend and found out that your ex was better?


  • What did your last girlfriend leave you for?


  • Would you ever forgive me if you find out that I have been cheating on you?


  • What is that one thing which made you choose your girlfriend over so many other fellow mates?


  • What if you had never met your girl? Do you think that you would have lived so happily?


  • If our parents don't accept your relationship, what do you think should be done then? Should you forcefully part?


Download the list of personal questions to ask your boyfriend below

Personal questions to ask your boyfriend - Download the list


Personal questions to ask your girlfriend

Personal questions to ask your girlfriend


  •  If one of your lovers realizes that you are playing a double dating game with them, how would you handle the situation?


  • Do you think it is okay to kiss your best friend out of excitement when you are already dating? 


  • Have you ever expressed your feelings to someone and then told them it was due to the dare-game?


  • Has it ever happened to you that you faked being interested in your boyfriend’s talk when you wanted to go?


  • Whom did you date for the longest? What was his good feature?


  • Do you think it is okay to judge a girl’s character depending on the number of relationships she had?


  • Did you feel like hitting your man hard because of the fights you were having?


  • Did you break up with your man just because of fun and wanted to see how it goes?


  • How much do you think you’re deserving of your man?


  • Have you already judged your man’s parents depending on his attitude towards you?


  • Have you ever tried to be rude to your parents just because they didn’t like your man?


  • Will you like to be head of the family and earn if your man refuses to do so?


  • Can you kiss someone out of compassion or pity and hide it from your boyfriend?


  • If your man is not rich but still loves you from the core of his heart, will you ever dump him?


  • Have you ever left someone for some silliest reason?


Download the list of personal questions to ask your girlfriend below

Personal questions to ask your girlfriend - Download the listNow that all the questions are done, what do you think the probable answers would be? Go on try them to everyone you know and get the never expected answers!


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