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

Last Updated: 19.06.2025 13:42

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

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

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

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

What was the first Native American tribe to inhabit Long Island, NY?

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

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

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

How are Hinduism and Sikhism related, considering they both originated in Punjab, India?

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

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

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

Why do we let ugly men exist?

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

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

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

Proba-3’s first artificial solar eclipse - European Space Agency

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

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

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

Why aren't you a Trump supporter?

*** Random Questions ***

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

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

When was the last time you had sex with someone much older than yourself?

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

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

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

Why did my ex-narcissist move so fast with his new supply marriage engagement moving in, etc.?

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

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

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

What one thing makes someone a very mature person?

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

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

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

How do you know when someone really loves you?

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

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

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

What if Supergirl was a baby and not a teenager when she left Krypton? Who do you think will find her? What do you think things would be like?

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

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

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

Why does Islam give a bad vibe?

Does the thought excite you? Care to share?

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

Do you watch it? What is your favorite?

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

Model/Photographer Police/Criminal

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

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

8- What are your thoughts on politics?

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

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

Any that are a turn off?

What is your favorite position? Why?

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

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

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

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

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?

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

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

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

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

62~ Have you used adult toys?

1- What’s your favorite animal? 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.?

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

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

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

Nothing too Serious

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

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

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

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

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

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

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

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

How old are you? Male or Female?

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

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

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

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

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

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

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

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

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

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

Master/Slave Boss/Maid

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

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

Family Relation Age Play

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

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?

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

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?

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

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

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

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

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

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

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

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

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

Would you read them together?

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

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

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

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

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

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

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

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

Have you ever? Care to Share?

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

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

Do you think this brought you closer together?

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

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

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

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…

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

10- List 5 of your top pet peeves.

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?

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

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

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

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

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…

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

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

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

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

*** Questions About Me ***

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

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

The Ice Breaker Questions

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

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,

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

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

18~ Who/when was your first “crush”?

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

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

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

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

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

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

*** What’s Your Favorite…? ***

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

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

*** Deal Breaker Questions ***

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

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

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

If you win, what will you make them do?

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

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

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

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

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

Doctor/Nurse Stripper/Client

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

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

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

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

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

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

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

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

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

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

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

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

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?

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

38~ Share your most embarrassing sexual memory?

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?

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

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

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

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

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

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

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

What was the longest? What was the shortest?

Teacher/Student Stranger/One Night Stand

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

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?

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

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

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

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

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

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

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

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

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

Repairman/Lonely Wife Virgin/Experienced

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

Please share Did you stop?

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

83~ How do you feel about Porn?

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

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

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

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

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

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

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

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

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

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?

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

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

89~ Do you like taking showers together?

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

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

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

*** Questions about Relationships/Past ***

Nurse/Patient Celebrity/Fan

42~ What’s your biggest regret in life?

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

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

(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…)

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

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

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

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

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

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

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

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

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

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?

47~ What would be your dream job and why?

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?

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)

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

52~ What are your hobbies?

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

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

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

Any that are a turn off?

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

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

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

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

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

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

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

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

39~ What are your love languages?

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

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

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

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

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

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

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

Over time has your thoughts on sex changed?

Escort/Client Job Applicant/Hiring Manager

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

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

Prisoner/Prison Guard Landlord/Tenant

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

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

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

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

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

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

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

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

If yes, what?

29- How superstitious are you?

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

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

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