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

Last Updated: 27.06.2025 04:48

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

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

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

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

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

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

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

Which country has the best and strictest legal system in the world?

Repairman/Lonely Wife Virgin/Experienced

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

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

Is it fair that 3rd world migrants and refugees are being put up in first class hotels in the UK when there are historic levels of homelessness and poverty?

38~ Share your most embarrassing sexual memory?

Escort/Client Job Applicant/Hiring Manager

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

Why does a lot of the YouTube community support the MGTOW movement?

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

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

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

Why are Republicans such intolerant people?

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

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…

Doctor/Nurse Stripper/Client

Is Daenerys Targaryen really the most beautiful woman, or is everyone saying that just to flatter her?

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

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

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

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

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

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

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

What is your favorite position? Why?

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

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

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

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

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

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

Why is Reagan seen as the best president in the USA when he literally destroyed the American economy with trickle down system and was strongly against worker unions?

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

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

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

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

Any that are a turn off?

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

Model/Photographer Police/Criminal

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)

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

Prisoner/Prison Guard Landlord/Tenant

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,

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

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

47~ What would be your dream job and why?

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

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

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

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

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

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

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

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

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

*** Questions About Me ***

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

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

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?

Does the thought excite you? Care to share?

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

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

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

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

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

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

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?

Would you read them together?

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

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

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

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

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

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

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

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

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

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

42~ What’s your biggest regret in life?

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

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?

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

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

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

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

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

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

Any that are a turn off?

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

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?

*** What’s Your Favorite…? ***

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

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

Teacher/Student Stranger/One Night Stand

Nothing too Serious

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

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

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

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

*** Random Questions ***

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

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

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

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

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

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

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

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

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

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

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

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

What was the longest? What was the shortest?

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

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

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

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

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

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

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

Have you ever? Care to Share?

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

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

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

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

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

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

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

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

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

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

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

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

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

29- How superstitious are you?

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…

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

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

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

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

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

If yes, what?

*** Questions about Relationships/Past ***

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

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

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

Over time has your thoughts on sex changed?

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

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

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

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

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

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

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

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

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

Do you watch it? What is your favorite?

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

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

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

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

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

Do you think this brought you closer together?

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

10- List 5 of your top pet peeves.

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

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

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

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

83~ How do you feel about Porn?

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

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?

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

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

8- What are your thoughts on politics?

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

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

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?

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

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?

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

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

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

89~ Do you like taking showers together?

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

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

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?

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

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

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

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

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

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

The Ice Breaker Questions

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

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

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

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

How old are you? Male or Female?

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

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

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

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

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

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

Master/Slave Boss/Maid

*** Deal Breaker Questions ***

Nurse/Patient Celebrity/Fan

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

Family Relation Age Play

18~ Who/when was your first “crush”?

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

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

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

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

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

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

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

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

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)

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

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

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

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

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

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

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

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

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

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

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

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

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

39~ What are your love languages?

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

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

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

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

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

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

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

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

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

52~ What are your hobbies?

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

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

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

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?

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

If you win, what will you make them do?

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

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

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

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

Please share Did you stop?

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

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

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

62~ Have you used adult toys?

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

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

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

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

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

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

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