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

Last Updated: 01.07.2025 05:41

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

Any that are a turn off?

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

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

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

8- What are your thoughts on politics?

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

What are the reasons for your political affiliation with the Democratic party? What are some aspects of the party that you support and some that you do not?

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

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

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

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

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

What was the longest? What was the shortest?

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

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

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

Why do a bra and panties have to match?

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

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

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

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

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

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

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

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

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

Has the CCP been the most successful systemat governing China, than any other top 5 global economy state over the last century?

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

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?

What is the reason that Worcester, Massachusetts is not as well-known as Boston and Springfield, even though it is a large city with many neighborhoods?

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

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

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

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*** Questions About Me ***

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

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

Why do we let ugly men exist?

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

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

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

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

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

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

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

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

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

Model/Photographer Police/Criminal

(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…)

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

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

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

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

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

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

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

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

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

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

Any that are a turn off?

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

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

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

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

52~ What are your hobbies?

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

The Ice Breaker Questions

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

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

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

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

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?

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

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

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

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

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

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

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

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

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

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

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

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

What is your favorite position? Why?

How old are you? Male or Female?

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

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

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

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

Master/Slave Boss/Maid

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

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

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

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

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

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

Nothing too Serious

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

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

42~ What’s your biggest regret in life?

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

Doctor/Nurse Stripper/Client

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

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

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

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

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

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?

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

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

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

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

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

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

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?

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

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

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

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

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

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

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

83~ How do you feel about Porn?

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…

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

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

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

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

Prisoner/Prison Guard Landlord/Tenant

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

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

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

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

18~ Who/when was your first “crush”?

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

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

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

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

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

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

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

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

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

47~ What would be your dream job and why?

89~ Do you like taking showers together?

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

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

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

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

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

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

Do you watch it? What is your favorite?

*** Random Questions ***

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,

Does the thought excite you? Care to share?

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

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

Have you ever? Care to Share?

Escort/Client Job Applicant/Hiring Manager

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

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

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

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)

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

Please share Did you stop?

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

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

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

*** What’s Your Favorite…? ***

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

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

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

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

29- How superstitious are 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?

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

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

Would you read them together?

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?

*** Questions about Relationships/Past ***

Nurse/Patient Celebrity/Fan

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

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

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?

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

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

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

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

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

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

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

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

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?

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?

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

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?

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

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

Family Relation Age Play

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

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

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

39~ What are your love languages?

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

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

Repairman/Lonely Wife Virgin/Experienced

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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…

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

Do you think this brought you closer together?

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

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

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

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

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

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

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

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

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

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

38~ Share your most embarrassing sexual memory?

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

If you win, what will you make them do?

*** Deal Breaker Questions ***

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

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

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

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

54~ Would you ever go skinny dipping 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…

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

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

10- List 5 of your top pet peeves.

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

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

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

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

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

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

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

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

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

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

If yes, what?

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

Teacher/Student Stranger/One Night Stand

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

62~ Have you used adult toys?

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

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

Over time has your thoughts on sex changed?

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

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