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

10.06.2025 11:35

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

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?

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

(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…)

Why are there so many girls and not enough boys to follow?

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

Repairman/Lonely Wife Virgin/Experienced

Prisoner/Prison Guard Landlord/Tenant

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

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

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

How does one succeed in life?

*** What’s Your Favorite…? ***

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

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

South Korean stocks rise 2% to lead gains in Asia after opposition leader wins presidential election - CNBC

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

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

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

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

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

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

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

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

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

What caused the decline of the Soprano crew?

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

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?

Does meth make women super horny like it does men?

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

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

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

When does a woman know she is cumming?

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

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?

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

Why do I have an itch in my labia, white gooey and thick discharge which doesn't have a smell but my vagina does sometimes and both me and my partner do not have STDs, what is it?

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

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

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

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

39~ What are your love languages?

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

Why does Boko Haram attack its own Muslims?

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

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

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

Do you ever feel like you are doing good, but would do better if people hadn’t blamed you or even bothered you? I have gotten lonely, but I always am up to something (creating my destiny).

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

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,

What was the longest? What was the shortest?

Are there girls here who like group sex?

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

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

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

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

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

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

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

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

52~ What are your hobbies?

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

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

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

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

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

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

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

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

Do you think this brought you closer together?

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

Escort/Client Job Applicant/Hiring Manager

How many partners have you had oral sex with? Who? 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?

Would you read them together?

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?

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

Nurse/Patient Celebrity/Fan

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

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

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

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?

Teacher/Student Stranger/One Night Stand

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

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

Master/Slave Boss/Maid

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

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

Does the thought excite you? Care to share?

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

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

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

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

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

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

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

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

*** Questions About Me ***

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

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

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

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

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

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

*** Deal Breaker Questions ***

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

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

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

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

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

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

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

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

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

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

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

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

The Ice Breaker Questions

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

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)

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

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

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

Doctor/Nurse Stripper/Client

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Family Relation Age Play

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

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

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

83~ How do you feel about Porn?

62~ Have you used adult toys?

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

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

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

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

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

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

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

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

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

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

10- List 5 of your top pet peeves.

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

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

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

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

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

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

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

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

42~ What’s your biggest regret in life?

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

29- How superstitious are you?

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

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

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

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

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

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

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

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

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

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

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

16~ Do you believe in “soulmates”? Have you found yours? Who? 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…

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

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

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

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

Model/Photographer Police/Criminal

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

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

89~ Do you like taking showers together?

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

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

If yes, what?

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

47~ What would be your dream job and why?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

18~ Who/when was your first “crush”?

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?

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

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

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

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

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

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?

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

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

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

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?

38~ Share your most embarrassing sexual memory?

*** Random Questions ***

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

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

How old are you? Male or Female?

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

Any that are a turn off?

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

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

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?

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

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

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

Nothing too Serious

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

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

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

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

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

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

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

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

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

What is your favorite position? Why?

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

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

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

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

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

8- What are your thoughts on politics?

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

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

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

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

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…

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

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

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?

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

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

If you win, what will you make them do?

Over time has your thoughts on sex changed?

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

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

Have you ever? Care to Share?

Please share Did you stop?

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

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

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

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

Do you watch it? What is your favorite?

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

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

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

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

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

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

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

*** Questions about Relationships/Past ***

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

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

Any that are a turn off?