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

10.06.2025 09:50

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

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?

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

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

What are Best Breakfast Places in Pune?

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

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

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

The workout supplement becoming more popular outside the gym - WTOP

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

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

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

Scoop: Treasury officials defend "revenge tax" from wary GOP senators - Axios

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

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?

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

What are the types of values?

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

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

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

The Surprising Way Five Days Of Junk Food Impacts Your Brain - MindBodyGreen

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

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

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

How do you identify a woman player?

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

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

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

500-Million-Year-Old Mystery Fossil Rewrites Early Animal Evolution - SciTechDaily

Nothing too Serious

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

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

Do other British people agree that the UK should reconquer Ireland?

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?

8- What are your thoughts on politics?

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

Dakota Johnson shows Chris Martin what he's missing post-breakup in completely sheer ensemble - Page Six

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

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

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

2 Jewish delis make the New York Times’ 2025 ‘Best Restaurants in New York City’ list - Jewish Telegraphic Agency

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

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

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…

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

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

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

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

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?

Does the thought excite you? Care to share?

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

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

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

If you win, what will you make them do?

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

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

*** Questions About Me ***

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

The Ice Breaker Questions

Escort/Client Job Applicant/Hiring Manager

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

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

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

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

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

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

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

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

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

*** Deal Breaker Questions ***

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

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

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

18~ Who/when was your first “crush”?

Any that are a turn off?

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

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

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

*** Questions about Relationships/Past ***

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

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

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

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

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

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

Would you read them together?

89~ Do you like taking showers together?

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

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

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

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

Master/Slave Boss/Maid

(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…)

If yes, what?

52~ What are your hobbies?

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

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

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

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

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

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

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

Please share Did you stop?

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

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

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

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

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)

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

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

39~ What are your love languages?

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

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

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.

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

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

62~ Have you used adult toys?

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

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

Nurse/Patient Celebrity/Fan

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

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

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

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

10- List 5 of your top pet peeves.

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

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

Prisoner/Prison Guard Landlord/Tenant

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,

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

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

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

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

Do you think this brought you closer together?

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

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

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

What is your favorite position? Why?

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

38~ Share your most embarrassing sexual memory?

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

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

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

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

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

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?

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

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?

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

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

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

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

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

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

*** Random Questions ***

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?

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

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

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

Any that are a turn off?

Repairman/Lonely Wife Virgin/Experienced

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

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

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

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

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

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

42~ What’s your biggest regret in life?

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

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

Do you watch it? What is your favorite?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Model/Photographer Police/Criminal

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

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

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

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

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

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

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

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

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

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

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

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

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

Have you ever? Care to Share?

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

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

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

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

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

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

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?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Over time has your thoughts on sex changed?

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

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

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

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

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

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

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

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

What was the longest? What was the shortest?

*** What’s Your Favorite…? ***

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

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

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

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

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

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

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

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

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

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

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

29- How superstitious are you?

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

83~ How do you feel about Porn?

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?

47~ What would be your dream job and why?

Doctor/Nurse Stripper/Client

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

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

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

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

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

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…

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

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

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

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

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

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

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

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

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

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

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

Family Relation Age Play

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

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

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

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

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

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

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

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

How old are you? Male or Female?

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