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

Last Updated: 03.07.2025 00:32

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

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

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

Doctor/Nurse Stripper/Client

Some men love anal sex more than vaginal sex. Why?

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

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

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?

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

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

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

Would Joe Biden stoop low enough to get Taylor Swift to endorse him hoping it wins votes from celebrity worshipping idiots?

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?

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

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

I think that being gay is wrong, but I treat gay people respectfully like any other person. Is it homophobic? Or offensive in any kind of way? Aren’t disagreement and discrimination two different things?

39~ What are your love languages?

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

62~ Have you used adult toys?

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

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

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

What are the best Jewish jokes?

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

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

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

What are some common examples of condescending behavior?

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

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)

Prisoner/Prison Guard Landlord/Tenant

Can supporters of gun control explain the purpose behind a gun registry?

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

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

Any that are a turn off?

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

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

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

What are some mind-blowing facts about Michael Jackson?

89~ Do you like taking showers together?

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

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

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*** Questions about Relationships/Past ***

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?

How would you advertise if you wanted to be a "tour guide" who can take you through the dark web while warning you what not to look at and not to click on?

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

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

Would you read them together?

What do dreams about dead people mean?

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…

Have you ever? Care to Share?

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

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Does the thought excite you? Care to share?

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

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

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

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

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

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

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

Please share Did you stop?

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

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

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

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

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

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

Do you watch it? What is your favorite?

*** Deal Breaker Questions ***

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

Nothing too Serious

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

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

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

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

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

*** Questions About Me ***

Teacher/Student Stranger/One Night Stand

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

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

Any that are a turn off?

29- How superstitious are you?

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

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

83~ How do you feel about Porn?

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

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

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?

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

(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…)

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

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

The Ice Breaker Questions

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

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

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

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?

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

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

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

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?

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

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

Model/Photographer Police/Criminal

How old are you? Male or Female?

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

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

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

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

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

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

Master/Slave Boss/Maid

What is your favorite position? Why?

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

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

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

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

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

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

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

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

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

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

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

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

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

1- What’s your favorite animal? 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?

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

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

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

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,

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

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

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

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

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

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

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

Escort/Client Job Applicant/Hiring Manager

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

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

8- What are your thoughts on politics?

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

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

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

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

If you win, what will you make them do?

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

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

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

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

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

Repairman/Lonely Wife Virgin/Experienced

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

*** What’s Your Favorite…? ***

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

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

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

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

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

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

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

38~ Share your most embarrassing sexual memory?

47~ What would be your dream job and why?

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

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

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

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

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

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

If yes, what?

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

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

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

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

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

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

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

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

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)

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

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

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

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

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

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

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

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

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

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

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

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

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

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…

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

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

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

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

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

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

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

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

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

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

*** Random Questions ***

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

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

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

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

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?

52~ What are your hobbies?

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

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

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

18~ Who/when was your first “crush”?

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

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

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

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?

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

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 think this brought you closer together?

Over time has your thoughts on sex changed?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

10- List 5 of your top pet peeves.

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

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

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

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

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

Nurse/Patient Celebrity/Fan

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

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

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

42~ What’s your biggest regret in life?

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

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

Family Relation Age Play

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

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

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

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?

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

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

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?

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

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

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

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?

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

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

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

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

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?

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

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

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

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

What was the longest? What was the shortest?

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

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

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