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

Last Updated: 23.06.2025 14:25

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

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

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

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

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

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

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

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Nothing too Serious

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

Over time has your thoughts on sex changed?

Which daily habits can help you keep a clear and positive mind?

*** What’s Your Favorite…? ***

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

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

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

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

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

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

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

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

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

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

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

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

What is your favorite position? Why?

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

What are some signs that someone may be being stalked by an organization or secret society? How can they find out for sure?

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

Do you think this brought you closer together?

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

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

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?

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

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

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

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

If the world was flat, would it be possible to see Mount Everest if it was on the other side of the Earth on a clear sunny day?

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

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

47~ What would be your dream job and why?

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

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

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

*** Questions about Relationships/Past ***

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

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

8- What are your thoughts on politics?

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

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

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

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

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

89~ Do you like taking showers together?

The Ice Breaker Questions

Have you ever? Care to Share?

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

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?

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

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

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,

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

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

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

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

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?

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?

52~ What are your hobbies?

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

39~ What are your love languages?

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

If you win, what will you make them do?

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

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

Model/Photographer Police/Criminal

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

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

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

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

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?

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

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

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

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

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

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

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

42~ What’s your biggest regret in life?

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

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

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

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

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

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

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

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

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

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

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?

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

Nurse/Patient Celebrity/Fan

38~ Share your most embarrassing sexual memory?

If yes, what?

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)

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

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

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

10- List 5 of your top pet peeves.

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

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

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?

Do you watch it? What is your favorite?

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

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

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

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

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)

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

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

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

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

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

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

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

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?

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

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

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?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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?

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

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

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

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

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

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

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

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

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

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?

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

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

What was the longest? What was the shortest?

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

Family Relation Age Play

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

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

Any that are a turn off?

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

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

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

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

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

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

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

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

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

Prisoner/Prison Guard Landlord/Tenant

62~ Have you used adult toys?

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

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

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

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

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

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

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

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

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

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

*** Deal Breaker Questions ***

Repairman/Lonely Wife Virgin/Experienced

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

83~ How do you feel about Porn?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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?

*** Random Questions ***

Escort/Client Job Applicant/Hiring Manager

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

18~ Who/when was your first “crush”?

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

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

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

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

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

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

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

(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…)

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

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

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

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

Please share Did you stop?

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

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

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

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

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

29- How superstitious are you?

Master/Slave Boss/Maid

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…

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

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

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

Teacher/Student Stranger/One Night Stand

*** Questions About Me ***

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

Does the thought excite you? Care to share?

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

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

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

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

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

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

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

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

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

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

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

17- What’s your favorite holiday? 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.

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

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

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

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

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

Doctor/Nurse Stripper/Client

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

How old are you? Male or Female?

Would you read them together?

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

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

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

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…

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

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

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

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

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

Any that are a turn off?

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

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

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