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

11.06.2025 11:49

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

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

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?

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

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

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

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

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

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

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

How do you like to be pegged?

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

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

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

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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?

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

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

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

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

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

My cantankerous beagle is very badly behaved at the dog park and always starts barking at the other dogs. Would pepper spray be an effective method to correct his inappropriate behavior?

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

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

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

Who has experienced what they called a happy accident (bestiality)?

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?

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

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

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

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

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 do women feel when they are in love?

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?

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

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

What was the most inappropriate thing your parent caught you doing as a teen? Was in the bedroom, I thought nobody else was home. My sister and I shared that bedroom but I knew she was gone. I didn’t know my dad was home though.

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

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

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

What do people with very high IQs do all day?

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

62~ Have you used adult toys?

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

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

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

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

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

10- List 5 of your top pet peeves.

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Over time has your thoughts on sex changed?

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

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

What do you think will be the biggest factor in determining whether Daniel Penny was justified in believing that Jordan Neely had posed a deadly threat in the manslaughter trial?

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

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

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

Any that are a turn off?

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

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

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

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

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

8- What are your thoughts on politics?

Model/Photographer Police/Criminal

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

Nurse/Patient Celebrity/Fan

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…

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

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

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

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

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

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

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

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

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

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

52~ What are your hobbies?

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

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

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

Do you think this brought you closer together?

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

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

83~ How do you feel about Porn?

18~ Who/when was your first “crush”?

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

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

Family Relation Age Play

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

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?

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?

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

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

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

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

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

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

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

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

29- How superstitious are you?

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

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

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

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

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

Have you ever? Care to Share?

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

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

*** Questions About Me ***

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

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

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

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

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

*** Deal Breaker Questions ***

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

*** What’s Your Favorite…? ***

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

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?

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

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

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

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

(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…)

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?

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

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

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

Any that are a turn off?

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

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

How old are you? Male or Female?

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

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

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

What was the longest? What was the shortest?

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

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

89~ Do you like taking showers together?

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

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

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

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

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

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

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

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

39~ What are your love languages?

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

Escort/Client Job Applicant/Hiring Manager

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

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

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

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

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

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

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

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

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

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

Would you read them together?

The Ice Breaker Questions

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

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

Does the thought excite you? Care to share?

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

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

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

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

Do you watch it? What is your favorite?

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

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

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

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

47~ What would be your dream job and why?

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…

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

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

Nothing too Serious

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

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

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

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

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

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

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

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

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

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

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

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

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

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

*** Questions about Relationships/Past ***

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

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

42~ What’s your biggest regret in life?

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

Teacher/Student Stranger/One Night Stand

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

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

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

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

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

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

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

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

Please share Did you stop?

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

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

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

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

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

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

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

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

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

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

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

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

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

Prisoner/Prison Guard Landlord/Tenant

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

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

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

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

What is your favorite position? Why?

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

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

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

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

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

If you win, what will you make them do?

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

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

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

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

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

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?

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

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

*** Random Questions ***

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

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

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

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

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

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

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

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

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

Repairman/Lonely Wife Virgin/Experienced

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

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

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

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

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

Master/Slave Boss/Maid

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

If yes, what?

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

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

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

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

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

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

38~ Share your most embarrassing sexual memory?

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

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

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

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

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

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

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

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

Doctor/Nurse Stripper/Client

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