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

Last Updated: 30.06.2025 01:26

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

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

52~ What are your hobbies?

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

If "thinking" affects feeling, and "feeling" affects thinking, then "why" does this not produce a never-ending circle?

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

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

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

If babies could write, what questions would they ask on Quora?

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

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

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?

Memorial Tournament 2025: Third-round tee times, pairings at Muirfield Village - Yahoo Sports

8- What are your thoughts on politics?

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

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

Jony Ive and Sam Altman’s AI Gadget Won’t Be ChatGPT in Your Ears - Gizmodo

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


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

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

Ms. Rachel Has Been In Touch With Olivia Munn, And Urges Fans To “Be Kind” To Her - BuzzFeed

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

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

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

How likely is it that Israel would target targets in Iran if there is a full-blown conflict?

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

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

Doctor/Nurse Stripper/Client

Five Risks for Stocks That Cloud the Outlook for the Second Half - Bloomberg

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

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

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

CNBC's UK Exchange newsletter: No easy answers for Reeves - CNBC

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

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

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

Kraken Deal Andre Burakovsky To Chicago - NHL.com

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


Prisoner/Prison Guard Landlord/Tenant

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

Why do I sweat so much at the gym?

Model/Photographer Police/Criminal

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

Please share Did you stop?

Can I wear a headscarf? I am a white female but I have super curly hair, like 3B - 3C. Recently, I've been putting my hair in a pineapple and putting a headscarf around it. Is that okay? I'm not trying to appropriate any cultures.

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

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

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

Why do black people prefer thick, curvy women?

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

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

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

Nintendo Releases First Look At Pokémon Scarlet And Violet Running At 60 FPS On Switch 2 - Game Informer

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

38~ Share your most embarrassing sexual memory?

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

What does it mean when someone leaves something in your house, your room to be exact, and when you tell them, they say they left it there on purpose?

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

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

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

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

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

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

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

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

42~ What’s your biggest regret in life?

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

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

Over time has your thoughts on sex changed?

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

Family Relation Age Play

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?

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

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

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

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

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

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

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

If you win, what will you make them do?

Escort/Client Job Applicant/Hiring Manager

Teacher/Student Stranger/One Night Stand

Would you read them together?

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

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

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

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

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

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

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

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

39~ What are your love languages?

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

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


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

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

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

89~ Do you like taking showers together?

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

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

Nurse/Patient Celebrity/Fan

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

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

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

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

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

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

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

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

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

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

47~ What would be your dream job and why?

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

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

The Ice Breaker Questions

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

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

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

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,

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

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

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

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

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

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

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

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

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

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

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

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

If yes, what?

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

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

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

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

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

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

Repairman/Lonely Wife Virgin/Experienced

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

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

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

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

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?

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

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

What is your favorite position? Why?

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

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

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

*** What’s Your Favorite
? ***

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

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

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

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

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

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

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

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

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

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

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?

*** Questions about Relationships/Past ***

62~ Have you used adult toys?

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

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

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

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

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


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

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

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

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

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

What was the longest? What was the shortest?

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

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)

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

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

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

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

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

*** Deal Breaker Questions ***

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

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

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

Any that are a turn off?

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

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

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

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

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

Any that are a turn off?

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


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

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

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

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

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

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

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

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?

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

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

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

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

Master/Slave Boss/Maid

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

*** Questions About Me ***

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

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

Nothing too Serious

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

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

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

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

Do you watch it? What is your favorite?

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

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

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

10- List 5 of your top pet peeves.

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

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

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

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

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?

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

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

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

83~ How do you feel about Porn?

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
)

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

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

29- How superstitious are you?

Does the thought excite you? Care to share?

*** Random Questions ***

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

18~ Who/when was your first “crush”?

Take the short quiz here @ Discover Your Love LanguageÂź - The 5 Love LanguagesÂź

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

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

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

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

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

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

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

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

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

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

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

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

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

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?

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

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

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

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

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

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

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

Do you think this brought you closer together?

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

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

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

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

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

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

Have you ever? Care to Share?

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

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

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

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

How old are you? Male or Female?

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

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

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

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

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?

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

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

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

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?

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

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

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

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