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What is the most interesting question you can ask to get to know someone?

Last Updated: 21.06.2025 01:51

What is the most interesting question you can ask to get to know someone?

37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?

48~ Do you have any siblings? Are you close to your family?

A comprehensive questionnaire, this should be a fun exercise to get to know each other. Try to give as much detail as possible when answering questions. You can go through this together and talk about each question or fill out the questionnaire as completely as you can and once you are done, go through each question together. If you have been together for a while, it is also fun to try to answer the questions for your partner. Remember this should be fun, so if you do not wish to answer a question you can “PASS” and not answer. Both should answer honestly and without judgement. (This is important, without judgement) I hope this helps you get closer and strengthens your relationship… You can learn a lot about the other person… and yourself…

Why do many women like tall men?

23- What is your dream job? What was it as a child?

21- What's your favorite way to spend a weekend or time off?

Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts

What do you think will be the biggest factor in determining whether Daniel Penny was justified in believing that Jordan Neely had posed a deadly threat in the manslaughter trial?

30- Do you prefer living in the countryside, in a town, or in a big city? Why?

60~ How important is oral sex? Do you like receiving? Do you like giving?

40~ What’s the weirdest place you’ve ever had sex?

Riddle: How do budget cuts, DEI hires, and empty reservoirs, turn the bluest, most Democrat city Red?

64~ When was your very first orgasm? When was your first from having sex? Care to share?

17- What’s your favorite holiday? What’s your least favorite?

2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.

If you received hand-me-downs as a child, how did they make you feel?

74~ Have you ever had sex while others watched? Have you ever watched others have sex?

*** What’s Your Favorite…? ***

Can you have multiple orgasms? Are you able to have different kinds of orgasms?

Having read so much about Archie and Lilibet not actually existing, does anyone have any proof that they not only exist but that Meghan gave birth to them?

83~ How do you feel about Porn?

12- What’s your favorite food? What’s your least favorite?

63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?

Why are there so many single moms in America?

Would you read them together?

Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®

Please share Did you stop?

Why does my vagina and around my butthole itch? I don't have weird discharge and I'm still a virgin.

39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?

Any that are a turn off?

Do you think this brought you closer together?

A Salute to Brian Wilson: Darian Sahanaja on Growing Up on Brian, Then Basking in His Musical Inner Circle for a Quarter-Century - Variety

These go from easy to answer, to OMG, you really want to know that?! to some serious thought. Take your time and have fun with this. The past is the past… it got you two here together…

47~ What would be your dream job and why?

5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?

Why did losers ban TikTok?

22- Do you have any birth marks? How about scars? Care to share how you got them?

24~ What are your expectations in a relationship? (I know a very big question, take your time)

59~ Have/do you masturbate? How often? What do you use? (Toys, Phone sex, Erotica, Hard Core, shower/water, etc) Would you, while your partner watches?

Islam is definitely a very anti-LGBTQ religion, so why don't liberals ever stage pro-LGBTQ demonstrations at mosques or at the consulates/embassies of Muslim countries?

9- Is there something you’ve always wanted to ask me but you’re afraid?

88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?

2- What’s your favorite color? Do you a least favorite?

Hello,hope y'all doin good, i came to Quora to share my strange story , a very weird one , a story when luck smiled at me ,maybe u will enjoy it , let's begin,have fun... A year ago ,I was a real porn addicted(btw I was 18) ,but never had sex before, I don't have a gf I didn't try to find one even ,always thinking to go to find a sex worker but then I just don't , everyday watching different bodies getting fucked and everyday enjoying. One day, I was watching porn, a big ass lady with big boobs ,just after seeing her the image of my female cousin poped in my mind, (let's introduce her : she's 35 years old , very big ass , nice boobs ,not very big but nice,always wearing tight clothes , she's divorced ) and I thought of me fucking her ,I never had sexual desires for her but now I do days went by and when I met her I was so horny ,I couldn't stay with the family cz my penis was clearly erected , I realized this is my first time I get horny for one of my family ,it not illegal in my country.well to make a long story short( if u want details just text me I will tell u 😊),I decided to give her signs that I want to fuck her,finally I decided to have sex and with my cousin , I thought it is the best beggining for me, i started touching her when I came across her in a narrow place , make her feel my hard cock when we hug , I thought it will hard and I will be ashamed but no , I felt nothing and she said nothing , probably she thought it was by mistake,anyways, I decided then to talk with her about sex, waited for her to be alone in a room and talk with her, I confessed everything about me watching porn and addicted..etc,she said it's normal and u are growing up and u must have sex,well at that time I was like whaaat????? Well I didn't control myself and asked her for sex ( horny like I Ve never been before) she said that she will think Abt it ,2 weeka went by then she called me ,telling that she reserved a room in a hotel and we meet tonight ,we met,and bruuhh, sex is great , I mean, I had to find a pirstitue ,what I was waiting for to have such a feeling ????, I will never forget that night, I started kissing her she was kissing hard ,she misses sex so bad , she sucked my dick and swallowed my semen ,I felt I'm in a dream , then when fucked ,her ass was very big and the anus was open ,didn't struggle to get my hard cock inside it , she was obviously missing sex , she was shouting ,fuck me yh fuck me , I go fast after every word until I cum , we did that 3 times , then we went to her pussy , using condoms I fucked her so hard the moans were higher , everything was perfect ,in the end I asked her to lick her body , licked pussy ,ass, boobs,then she sucked my cock until we sleeped ,all I know that she was dirty ,well before even having sex with her I knew she is an open minded woman , and a woman that looks that she donesnt know anything , but she knows everything, but never expected having sex with her ,well she was horny and that helped...but no one of us regretted that sex ever.. We still have sex from time to time ,and I started having sex with sex workers , joining threesomes..etc If u want pics of her text me.

What was the longest? What was the shortest?

Would /have you ever given your partner a lap dance and Striptease?

51~ What tends to bring a smile to your face?

78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?

Repairman/Lonely Wife Virgin/Experienced

Any that are a turn off?

How many partners have you had oral sex with? Who? Care to Share?

52~ What are your hobbies?

35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?

53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?

How long for foreplay? Do you need to have an orgasm? Is afterplay important?

69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?

Do you like the “69” position? Do you prefer to be on top or bottom?

6- Do you have dreams? Can you remember them? What do you usually dream about?

42~ What’s your biggest regret in life?

4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)

43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?

22~ What is the best pickup line anyone has ever used on you? What was the worst?

32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?

6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?

Would you mind if your partner watched it? How about together vs alone?

9- If you could have three wishes, what would they be? Why?

13~ Is there a difference between, making love, having sex, and fucking?

Are you willing to help and encourage your partner to fulfill their fantasies and desires?

81~ Do you have any kinks and/or fetishes?

37- Do you like your name? If you could change it, what would you change it too?

42~ Ever been spanked during sex? Did you like it? Would you like me to do it?

Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…

82~ Do you have any fantasies involving Role-Playing?

84~ How do you feel about reading/listening to adult stories?

(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?

Do you watch it? What is your favorite?

4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)

Escort/Client Job Applicant/Hiring Manager

If you say it, I will stop, and we can talk about it when you are ready.

8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.

Do you shave/trim your pubic hair? For you guys do you shave your balls?

76~ Have you had a threesome? Care to Share?

72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?

47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)

*** Deal Breaker Questions ***

30~ What's something unexpected that turns you on?

11- How about if they like a certain sports team? 12-How about drinking too much?

75~ If your partner wants an orgasm/have sex when you don't desire to have sex, how do you plan to deal with their needs?

Meaning if you ever say it no matter how long we have been together or where we are in the moment…

Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?

68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?

6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?

What’s the longest time you gone without having sex, after, having it? How much time between the others?

* Which of the following turns you on the most? Do you have any not on this list? Care to share?

Would you allow me to shave your legs? How about your pubic hair? How about shower sex?

3- What was the most surprising thing you’ve learned about me throughout our relationship?

38- If you won the Lottery and got 200 million dollars, what would you do with all that money?

Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?

1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)

*** Random Questions ***

66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?

Model/Photographer Police/Criminal

Can you Deep Throat? Do you like the taste of yourself?

8- What are your thoughts on politics?

1~ How old were you when you had your first kiss? Who? Care to Share?

85~ If you gave me a “free Pass” to have me do anything for one hour, what would you want me to do to you?

12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?

Would you allow me to clean every part of your body with my soapy hands and fingers?

73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?

54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?

38~ Share your most embarrassing sexual memory?

Will you cheat again? How can, you be sure? Define what cheating is to you.

What have you learned about me that was new and/or surprising?

57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?

14- What is an embarrassing moment in your life? How about your most embarrassing?

3- What Superhero or Superpower would you want to be/have?

If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)

10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?

Family Relation Age Play

45~ How do you feel about me blindfolding you? How about blindfolding me?

Will you kiss after your partner has gone down on you? Swallow or spit semen?

Does the thought excite you? Care to share?

33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?

16- Can we talk about your health history? Have you had any surgeries? Any broken bones?

29~ What are some things that turn you off? What is your biggest turn off?

46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?

28- What are some things that people do that irritate you?

*** Questions About Me ***

19- Do/have you smoked? What do you prefer? How often?

1- What’s your favorite animal? Do you a least favorite?

9- What’s your favorite season and why? What’s your least favorite?

10- List 5 of your top pet peeves.

9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?

17- Have you ever done drugs? Which ones? How often?

Over time has your thoughts on sex changed?

14- Do you have a “Deal Breaker”, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?

9~ How many times over your lifetime do you think you have had sex so far?

35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?

22- What is your favorite childhood memory? What is your least favorite?

11- What's your favorite restaurant? What’s your least favorite?

How old are you? Male or Female?

Teacher/Student Stranger/One Night Stand

7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?

33- Beach or Mountains? Or is there another place to like better?

17~ What is the average length of your relationship(s)? What was the longest? Why did they end?

16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?

55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?

Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?

3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)

2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?

7- What if a person smells a certain way? 8- How about smoking?

14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?

50~ How many children do you have? What are their ages?

That one or two things that made you go hmmmm, OMG or wow!

3- Should Pluto still be considered a planet? 4- How about smoking?

80~ Share your top three fantasies/desires. (Be detailed) 😊

6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?

92~ Everyone needs a “safe” word. What is yours?

77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?

13- What is the craziest/scariest thing you've ever done?

Would you do it again, and would you rather 2 females or 2 males?

39~ What are your love languages?

18- What’s your favorite way to relax after a long day? What’s your least favorite?

Nurse/Patient Celebrity/Fan

26~ What side of the bed do you sleep on?

4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?

13- How about having a certain hair cut/style?

10~ How many dates are necessary before you to have sex with someone?

20- What’s your favorite candy? What’s your least favorite?

How many times do you think you have “made love”?

If YES, was it with 2 men or 2 women? Did you enjoy it?

What is your view on sex? Meaning, When/Where/ How often/

62~ Have you used adult toys?

19- What’s your favorite fairytale? What’s your least favorite?

If you win, what will you make them do?

If you lose, are you willing to be their sex slave for a day, (anything goes)?

What is your favorite toy? Ever wanted to try a specific toy?

You know that I will be 100% truthful, so ask.

25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?

85~ If I gave you a “Free Pass” for you to do anything to me for one hour, knowing that no matter what you did,

Is it ok for a man to perform oral sex after he has ejaculated inside of you?

36- Do you play video games? What is your favorite? Do you a least favorite?

71~ Would you give your partner a hand or foot job? Would you receive one?

Do you have a favorite? Is it ok if your partner does?

Doctor/Nurse Stripper/Client

I would allow you to do it… What would you do to me?

20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?

70~ Would/do you have/like anal sex?

Do you like it when they show and tell you what they want?

40~ If you could go back in time, and relive your life, with the knowledge you have now, what age would you go back to and why?

*** Questions about Relationships/Past ***

32- What's your greatest talent? Can I see it right now?

58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?

49~ If you could, would you want to be the opposite sex for a day, week, or year?

43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?

The Ice Breaker Questions

19~ Who/when was your first “heartbreak”?

50~ Where would you like to be touched more? Do you have a place that you want to be touched, that no one has, or has only happened a couple times? How about less?

If yes, what?

15~ Have you ever been “in love”? Who? Care to Share?

5~ When you first started having sex, was it what you thought it would be?

Prisoner/Prison Guard Landlord/Tenant

26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?

34~ Do you like the lights on or off during sex?

Nothing too Serious

Would you ever want to be woken up with oral and/or intercourse?

51~ Are you willing to play adult games with your partner?

11~ Have you ever been caught by your parents or children or others while having sex?

29- How superstitious are you?

31- If given a chance to be immortal, would you take it? Why?

41~ Are there moments in your past that you would want to change? Please share 3 of them.

12- What is the weirdest thing you've ever eaten?

Get this wrong and this could mean the end… :-) some funny, some not…

(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couples’ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETC…)

89~ Do you like taking showers together?

Master/Slave Boss/Maid

21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?

28~ What are some things that turn on? What is your biggest turn on?

56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?

15- What's your favorite saying? What word or phrase is your least favorite?

41~ What are you best at in bed? What do you think you are not so good at? Anything you want to get good at?

What do you dislike about me? I asked you to be 100% honest.

11- List at least 5 things on your bucket list. Have you done any of them already?

33- If you could visit any time period, when would you pick? Please explain why?

20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?

18- How often do you drink alcohol? What is your favorite drink?

53~ How much can you tell me about the one thing you are most passionate about?

8- What's your favorite flavor of ice cream? Do you a least favorite?

13- What’s your favorite drink? What’s your least favorite?

14- What's your favorite dessert? Do you a least favorite?

14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?

15- What bad habit do you wish you could quit? Do you have any addictions?

3- What’s your favorite smell? Do you a least favorite?

31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)

87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?

What would you say to prove to yourself that it was really you?

25~ How do you feel about PDA? (Public Display of Affection)

44~ Have you ever been tied up during sex? What are your thoughts on bondage?

11- Is there something you would like me to do, in any area of our relationship that I have not done, or you want more of?

93~ Now that this really long questionnaire is over, one last question, ok maybe 3…

8~ How many times a week would you like to engage in sexual activities? What is the average for you now?

27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.

How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)

Have you ever? Care to Share?

7- What are your thoughts on religion? Is there an afterlife?

10- What is your favorite family tradition? What’s your least favorite?

Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?

5- What do I do outside the bedroom that turns you on? How about, what turns you off?

What is your favorite position? Why?

45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)

46~ Have you ever used furniture, or other types of things to aid you while having sex?

16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?

61~ How willing would you be to try new sexual positions?

5- Have you ever been hypnotized? Would you allow yourself to be?

5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?

92~ Have you ever had or have an STD? How many? What was it?

90~ Have you ever had sex in a Pool or Hot Tub? Would you?

How well do you know me? And some of your thoughts about me

65~ Describe the best orgasm you’ve ever had? Care to share?

If NO, would you ever have one? Would it be with 2 men or 2 women?

44~ Care to share something about yourself that no one else knows about you?

79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?

27- What was/ is nickname? Does it have a meaning behind it?

How about if they talk dirty and/or call you names?

7~ How many times in one day have you had sex? Who/When/Where? Care to Share?

21~ What was the best date you ever went on? What has been the worst?

23~ What do you believe is required to have a successful and healthy relationship? (This is important, take your time, and really think about this)

24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?

* Give a rating for each one (0-100)

36~ What is your favorite time of day to have sex/make love?

7-What do I do in bed that drives you wild? How about, what turns you off?

2~ How old were you when you got to 2nd base? (Tongue kissing, breast feeling, or outside the clothes genital contact) Who? Care to Share?

52~ Are you willing to make “those types” of bets with your partner?

91~ Would you ever go into an adult book/toys store with me? Would you buy something?

1- What was your first impression of me? Has it changed?

49~ How many times have you been married? Why did they end?

1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?

4- For a pet, Cat, dog or other?

67~ Do you like it when your partner moans and/or is vocal during sex?

48~ Have you ever paid or been paid for sex?

What have you learned about yourself that you did not before this?

34- Ever been to a concert? What was your favorite? Who would you like to see?

18~ Who/when was your first “crush”?