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

09.06.2025 06:27

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

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

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

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

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Doctor/Nurse Stripper/Client

(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…)

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

Why do people say "tall, dark, and handsome" when they actually mean "tall, white, and handsome"?

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

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

52~ What are your hobbies?

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

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

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

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

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

What is your worst experience in life?

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

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

*** Questions about Relationships/Past ***

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Any that are a turn off?

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

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?

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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?

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

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

What's the biggest myth about illegal immigrants?

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

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

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

Is using tech to track or monitor your partner’s activities a sign of love, insecurity, or control?

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

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

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

I refuse to date any women that are social media influencers, content creators, TikTok celebrities, and use Only fans. Would this be seen as normal, or would I be going too far? Why?

Prisoner/Prison Guard Landlord/Tenant

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

How old are you? Male or Female?

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

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

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

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

Does the thought excite you? Care to share?

Have you ever? Care to Share?

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

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

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

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

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

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

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

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

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

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

*** Deal Breaker Questions ***

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

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

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

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

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

Model/Photographer Police/Criminal

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

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

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

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

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

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

8- What are your thoughts on politics?

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

62~ Have you used adult toys?

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

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

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

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

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

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

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

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

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

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

83~ How do you feel about Porn?

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

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

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

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

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

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

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

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

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

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?

10- List 5 of your top pet peeves.

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

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

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

Please share Did you stop?

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

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

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

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

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

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

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

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

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

*** What’s Your Favorite…? ***

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

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

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

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

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

Nothing too Serious

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

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

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

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

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

Over time has your thoughts on sex changed?

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

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

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

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

89~ Do you like taking showers together?

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

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

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

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

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?

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

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

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

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

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

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

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?

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?

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

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

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

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

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…

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

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

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

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

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

Escort/Client Job Applicant/Hiring Manager

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

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

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

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

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

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

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

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

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

Would you read them together?

What is your favorite position? Why?

*** Questions About Me ***

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

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

What was the longest? What was the shortest?

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

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

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

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

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

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

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

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

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

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

18~ Who/when was your first “crush”?

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

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

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

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

If you win, what will you make them do?

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

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

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

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

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

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

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

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

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?

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

Repairman/Lonely Wife Virgin/Experienced

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

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

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

Any that are a turn off?

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

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

Master/Slave Boss/Maid

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

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

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

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

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

29- How superstitious are you?

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

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

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

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

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

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

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

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

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

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

The Ice Breaker Questions

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

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

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

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

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

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

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

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

*** Random Questions ***

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

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

Teacher/Student Stranger/One Night Stand

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

Do you think this brought you closer together?

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

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

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

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

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

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

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

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

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

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

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?

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

42~ What’s your biggest regret in life?

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

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

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?

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)

38~ Share your most embarrassing sexual memory?

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

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

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

39~ What are your love languages?

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

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

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

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

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

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

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

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

Family Relation Age Play

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

Nurse/Patient Celebrity/Fan

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

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

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…

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

47~ What would be your dream job and why?

Do you watch it? What is your favorite?

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

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

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

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

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

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?

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

If yes, what?