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

09.06.2025 09:16

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

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

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

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

Do narcissists love their children?

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

Teacher/Student Stranger/One Night Stand

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

Aristo Sham of Hong Kong wins the 2025 Van Cliburn Piano Competition - Dallas News

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

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

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

The Apple AirPods Pro and AirPods 4 Drop to the Lowest Prices of the Year for Father's Day - IGN

If yes, what?

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

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

US growth likely to slow to 1.6% this year, hobbled by Trump's trade wars, OECD says - ABC News

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

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

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

Julio Rodríguez addresses robbery at his home - MLB.com

8- What are your thoughts on politics?

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

CVS closing 271 stores, including 3 locations in Upstate NY - Syracuse.com

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

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

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

What the Spurs will do with the second pick - Pounding The Rock

18~ Who/when was your first “crush”?

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

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

Can a relationship really last forever?

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?

Please share Did you stop?

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

If you caught a shoplifter at your yard sale, how would you handle it?

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…

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

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

President Trump kicked Zelensky out of the White House. Is it over for a deal?

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?

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

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

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

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

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

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

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

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

52~ What are your hobbies?

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

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

*** Questions about Relationships/Past ***

42~ What’s your biggest regret in life?

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

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

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

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

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

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

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

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

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

*** Questions About Me ***

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

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

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

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

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

Doctor/Nurse Stripper/Client

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

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

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

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

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

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

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

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

Nurse/Patient Celebrity/Fan

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

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

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

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

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?

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)

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

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

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

Prisoner/Prison Guard Landlord/Tenant

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

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

Repairman/Lonely Wife Virgin/Experienced

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

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

83~ How do you feel about Porn?

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

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

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?

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

Any that are a turn off?

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

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

If you win, what will you make them do?

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

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

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

How old are you? Male or Female?

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

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

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

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

The Ice Breaker Questions

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

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

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

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

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

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

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…

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

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

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

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

*** Deal Breaker Questions ***

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

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

Would you read them together?

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

(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…)

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

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

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

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

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

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

38~ Share your most embarrassing sexual memory?

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

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

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

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

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

Any that are a turn off?

Do you think this brought you closer together?

Family Relation Age Play

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?

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

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

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

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

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

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

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

62~ Have you used adult toys?

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?

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

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

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

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

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

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

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

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

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

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

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

*** Random Questions ***

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

39~ What are your love languages?

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

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

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

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

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

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

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

Model/Photographer Police/Criminal

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

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

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

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

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

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

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

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

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

Does the thought excite you? Care to share?

Master/Slave Boss/Maid

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

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

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

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

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?

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?

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

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?

Escort/Client Job Applicant/Hiring Manager

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

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

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

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

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

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

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

89~ Do you like taking showers together?

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

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

What was the longest? What was the shortest?

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

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

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

10- List 5 of your top pet peeves.

Do you watch it? What is your favorite?

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

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

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

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

*** What’s Your Favorite…? ***

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

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

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

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

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

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

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.

What is your favorite position? Why?

47~ What would be your dream job and why?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Over time has your thoughts on sex changed?

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

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

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

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

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

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

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

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

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

Have you ever? Care to Share?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

29- How superstitious are you?

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

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

Nothing too Serious

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

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

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