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

10.06.2025 03:48

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

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

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

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

Why is it that when the Democrats absolutely love everyone to be LGBTP, they don't even acknowledge that Barack Obama and his husband Big Mike are homosexual, and he is the first homosexual president of the USA?

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

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

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

Why does NASA's Perseverance rover keep taking pictures of this maze on Mars? - Space

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

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

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

How do you get started in bestiality with a dog as a male?

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

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?

89~ Do you like taking showers together?

In Italy, how do people greet each other when they meet for the first time (e.g., on the street)? What's a good response to that greeting if you're not from Italy or don't speak Italian fluently yet?

What was the longest? What was the shortest?

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

Please share Did you stop?

Astronomers Astonished by Largest Explosion Since the Big Bang - futurism.com

Any that are a turn off?

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

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

Elon Musk threatened to decommission Dragon spacecraft. Here's what that would mean for NASA - ABC News

Master/Slave Boss/Maid

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?

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

Can you recommend a simple song with an awesome solo? What makes the solo stand out?

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

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

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

Pregnant women warned against using weight-loss jabs - BBC

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

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

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

Samsung could drop Google Gemini in favor of Perplexity for Galaxy S26 - Ars Technica

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

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

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

Cosmic Dawn with Nobel Laureate John Mather - NASA (.gov)

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

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

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

CVS is shutting down 271 stores in 18 states. Is your pharmacy affected? - NJ.com

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

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

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

What is the difference between heaven and heavens?

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.

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

Do people really never face any hidden costs or surprises with surgeries in countries with single-payer healthcare like the NHS?

83~ How do you feel about Porn?

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

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

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

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

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

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

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

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

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

Doctor/Nurse Stripper/Client

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?

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

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

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

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

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

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

Nothing too Serious

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

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

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

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

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

18~ Who/when was your first “crush”?

*** Random Questions ***

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

29- How superstitious are you?

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

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

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

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

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

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

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

Over time has your thoughts on sex changed?

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

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

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

Prisoner/Prison Guard Landlord/Tenant

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

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

If yes, what?

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

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

What is your favorite position? Why?

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

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

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?

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

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?

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

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

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

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

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

*** What’s Your Favorite…? ***

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

38~ Share your most embarrassing sexual memory?

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?

Repairman/Lonely Wife Virgin/Experienced

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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?

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

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

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

*** Questions about Relationships/Past ***

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

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

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

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

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

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

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

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

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

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

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

Does the thought excite you? Care to share?

Model/Photographer Police/Criminal

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

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

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

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

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

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

Any that are a turn off?

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

The Ice Breaker Questions

*** Deal Breaker Questions ***

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

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

Nurse/Patient Celebrity/Fan

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?

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

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

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

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

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

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

47~ What would be your dream job and why?

Escort/Client Job Applicant/Hiring Manager

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

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

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

Do you think this brought you closer together?

Do you watch it? What is your favorite?

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

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

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

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

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

52~ What are your hobbies?

42~ Ever been spanked 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?

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

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

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

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

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

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

Would you read them together?

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

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

39~ What are your love languages?

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

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

62~ Have you used adult toys?

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

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

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

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

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

21- Do you have any piercings? 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?

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

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

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

(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…)

Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ

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

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

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

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

*** Questions About Me ***

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

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

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

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

Teacher/Student Stranger/One Night Stand

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

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

8- What are your thoughts on politics?

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

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

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

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

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

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

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

How old are you? Male or Female?

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

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

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

10- List 5 of your top pet peeves.

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

Have you ever? Care to Share?

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

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

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

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

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

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)

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

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?

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

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

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

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

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

42~ What’s your biggest regret in life?

Family Relation Age Play

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…

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

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

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

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

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

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

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

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

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

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

If you win, what will you make them do?

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

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

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

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

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

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

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

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

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

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

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,

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