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

12.06.2025 12:45

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

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?

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

Where can I sell naked pics of myself online?

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

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

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

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

If you win, what will you make them do?

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

Why do Indian parents force their kids to do stuff?

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

*** Random Questions ***

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

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

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

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

James Hagens’ Islanders homecoming is no longer just a pipe dream - New York Post

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

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

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

Are you happy with your life?

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

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

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

Why did I move on so fast from a relationship that was my whole life and I was so attached, I moved on by 2 months?

42~ What’s your biggest regret in life?

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

Prisoner/Prison Guard Landlord/Tenant

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

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

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?

What happened to The Simpsons deleted onscreen footage?

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

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

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

Are there any queer Space Marine Legion in Warhammer 30k or 40k?

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

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

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

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

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

8- What are your thoughts on politics?

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

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

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

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

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

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

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

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

If yes, what?

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

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

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

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

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?

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

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

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

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

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?

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

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

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

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

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

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

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

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…

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

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

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

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

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

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

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

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

10- List 5 of your top pet peeves.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(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…)

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

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

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

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

39~ What are your love languages?

89~ Do you like taking showers together?

Nurse/Patient Celebrity/Fan

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

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

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

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

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

Teacher/Student Stranger/One Night Stand

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

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

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

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

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

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

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

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

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

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

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

Would you read them together?

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

*** Deal Breaker Questions ***

Does the thought excite you? Care to share?

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

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

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

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

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

29- How superstitious are you?

Doctor/Nurse Stripper/Client

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

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

Family Relation Age Play

Do you watch it? What is your favorite?

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

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

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

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

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

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

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?

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

*** What’s Your Favorite…? ***

52~ What are your hobbies?

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…

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

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

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

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

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

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

*** Questions About Me ***

Have you ever? Care to Share?

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

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

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

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

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

Any that are a turn off?

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

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

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?

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

The Ice Breaker Questions

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

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

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

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

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

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

Do you think this brought you closer together?

Master/Slave Boss/Maid

47~ What would be your dream job and why?

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

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

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

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

Nothing too Serious

62~ Have you used adult toys?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Repairman/Lonely Wife Virgin/Experienced

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

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?

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

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

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?

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

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

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

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

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

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

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

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

Model/Photographer Police/Criminal

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

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

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

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

Please share Did you stop?

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

Any that are a turn off?

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

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

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

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

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

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

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

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

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

83~ How do you feel about Porn?

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

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

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

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

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

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?

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

What is your favorite position? Why?

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

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

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

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

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

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

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

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

18~ Who/when was your first “crush”?

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

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

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

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

How old are you? Male or Female?

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

38~ Share your most embarrassing sexual memory?

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?

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

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

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

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

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

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

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?

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

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

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

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

Over time has your thoughts on sex changed?

*** Questions about Relationships/Past ***

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

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