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

12.06.2025 00:07

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

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

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

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

When a black man and a white woman have a child, does the child become white? If a white man and a black woman have a child, does the child become black?

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

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

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

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

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

Any that are a turn off?

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

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

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

What exactly is female squirting? Is it only urine or a combination of liquids?

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

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

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

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

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

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

Can a cop pull you over walking home asking why you are out so late?

Family Relation Age Play

52~ What are your hobbies?

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

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

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

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?

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

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

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

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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?

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

89~ Do you like taking showers together?

Can I use the LEG PRESS to build muscle?

Teacher/Student Stranger/One Night Stand

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

Please share Did you stop?

What is your age now, and what age do you prefer to stay at forever?

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

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

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

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47~ What would be your dream job and why?

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

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

What is the reason for The Acolyte (2024 series) having poor reception among Star Wars fans?

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

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

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

Why do most men who date ugly women brag like it's some big accomplishment, when any guy can pull an ugly woman?

Over time has your thoughts on sex changed?

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

Repairman/Lonely Wife Virgin/Experienced

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

*** What’s Your Favorite…? ***

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

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

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?

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

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

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

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

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

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

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

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?

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

83~ How do you feel about Porn?

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

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

*** Deal Breaker Questions ***

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

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

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

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

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?

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

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

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

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

The Ice Breaker Questions

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

42~ What’s your biggest regret in life?

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

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

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

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

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

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

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

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

62~ Have you used adult toys?

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

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

Escort/Client Job Applicant/Hiring Manager

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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?

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

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

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

10- List 5 of your top pet peeves.

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

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

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?

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

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

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

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

Have you ever? Care to Share?

Do you watch it? What is your favorite?

Nurse/Patient Celebrity/Fan

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

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

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

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

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

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

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

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…

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

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

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

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

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

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?

If you win, what will you make them do?

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

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

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

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

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

*** Questions About Me ***

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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)

What is your favorite position? Why?

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

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

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

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

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?

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

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

29- How superstitious are you?

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

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

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

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

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

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

What was the longest? What was the shortest?

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

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

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

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

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

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

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

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

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

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

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…

(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…)

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

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

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

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

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

8- What are your thoughts on politics?

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

Master/Slave Boss/Maid

39~ What are your love languages?

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

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

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

Any that are a turn off?

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

*** Random Questions ***

Model/Photographer Police/Criminal

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

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

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

18~ Who/when was your first “crush”?

38~ Share your most embarrassing sexual memory?

Would you read them together?

Doctor/Nurse Stripper/Client

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

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

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

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

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

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?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

How old are you? Male or Female?

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

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

Do you think this brought you closer together?

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

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

Nothing too Serious

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

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

Does the thought excite you? Care to share?

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

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

*** Questions about Relationships/Past ***

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

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?

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

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

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

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,

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

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

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

If yes, what?

Prisoner/Prison Guard Landlord/Tenant