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

09.06.2025 03:06

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

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

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

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

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

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

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

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

If you win, what will you make them do?

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

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42~ What’s your biggest regret in life?

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

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

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

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

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

Are rich people harder workers than poor people as a whole?

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

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

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

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

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

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

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

52~ What are your hobbies?

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

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

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

Master/Slave Boss/Maid

Why do I feel worthless most of the time?

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

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

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

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

Over time has your thoughts on sex changed?

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

Why has my ex moved on so fast after years of being together with me?

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

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

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

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

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

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

There was this one weird Bollywood movie that was released in the 2000s. Amitabh Bachchan was starring with another actress and the story was about how the old guy (Amitabh Bachchan) fell in love with the young woman. What is the name of this movie?

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?

Doctor/Nurse Stripper/Client

How old are you? Male or Female?

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

*** What’s Your Favorite…? ***

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

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

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

*** Random Questions ***

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

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

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

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

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

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

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

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

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

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?

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

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

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

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

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

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

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

Please share Did you stop?

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

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

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

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

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…

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

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

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?

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

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

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

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

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

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

*** Questions About Me ***

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

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

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

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

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

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?

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

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

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?

Model/Photographer Police/Criminal

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

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

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

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

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

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

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

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

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

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

What is your favorite position? Why?

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

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,

Any that are a turn off?

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

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?

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

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

89~ Do you like taking showers together?

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

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

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

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

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

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

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

Prisoner/Prison Guard Landlord/Tenant

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

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

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

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

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

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

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

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

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

38~ Share your most embarrassing sexual memory?

39~ What are your love languages?

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

Family Relation Age Play

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

Do you watch it? What is your favorite?

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

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

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

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

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

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

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

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?

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

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

8- What are your thoughts on politics?

What was the longest? What was the shortest?

10- List 5 of your top pet peeves.

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

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

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

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

Would you read them together?

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

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

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

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

29- How superstitious are you?

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

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

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

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

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

Teacher/Student Stranger/One Night Stand

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?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(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…)

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

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

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

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

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

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

Have you ever? Care to Share?

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)

47~ What would be your dream job and why?

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?

62~ Have you used adult toys?

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

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?

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

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

Nothing too Serious

Escort/Client Job Applicant/Hiring Manager

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

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

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

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

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

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

Any that are a turn off?

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

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

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

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

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

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

Repairman/Lonely Wife Virgin/Experienced

18~ Who/when was your first “crush”?

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

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

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

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

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

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

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

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

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…

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

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

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?

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

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

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

83~ How do you feel about Porn?

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

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

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

Does the thought excite you? Care to share?

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

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

Do you think this brought you closer together?

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

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

*** Questions about Relationships/Past ***

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

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

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

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

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

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

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

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

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

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

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

Nurse/Patient Celebrity/Fan

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

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

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

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

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

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

If yes, what?

The Ice Breaker Questions

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

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

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

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

*** Deal Breaker Questions ***

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

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

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)

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