What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 06:49
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Master/Slave Boss/Maid
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What was the first Native American tribe to inhabit Long Island, NY?
What have you learned about yourself that you did not before this?
Have you ever? Care to Share?
Teacher/Student Stranger/One Night Stand
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
13- What is the craziest/scariest thing you've ever done?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Have you ever been forced to undress for money just once?
17- Have you ever done drugs? Which ones? How often?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
71~ Would you give your partner a hand or foot job? Would you receive one?
What are some things that normal people do that religious people call sins?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What is your review of Hartley`s High School, Kolkata?
That one or two things that made you go hmmmm, OMG or wow!
3- What Superhero or Superpower would you want to be/have?
7- What are your thoughts on religion? Is there an afterlife?
Is it possible to revive a dead person in real life with black magic?
53~ How much can you tell me about the one thing you are most passionate about?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Would you read them together?
51~ What tends to bring a smile to your face?
*** Questions about Relationships/Past ***
What would you say to prove to yourself that it was really you?
92~ Everyone needs a “safe” word. What is yours?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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Prisoner/Prison Guard Landlord/Tenant
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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49~ If you could, would you want to be the opposite sex for a day, week, or year?
32- What's your greatest talent? Can I see it right now?
23- What is your dream job? What was it as a child?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
28- What are some things that people do that irritate you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Any that are a turn off?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What have you learned about me that was new and/or surprising?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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’s Your Favorite…? ***
44~ Care to share something about yourself that no one else knows about you?
76~ Have you had a threesome? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
11- How about if they like a certain sports team? 12-How about drinking too much?
Model/Photographer Police/Criminal
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?
11~ Have you ever been caught by your parents or children or others while having sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
If you win, what will you make them do?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
Can you Deep Throat? Do you like the taste of yourself?
Would you mind if your partner watched it? How about together vs alone?
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?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
1~ How old were you when you had your first kiss? 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?
9- If you could have three wishes, what would they be? Why?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
70~ Would/do you have/like anal sex?
Do you like it when they show and tell you what they want?
18~ Who/when was your first “crush”?
Family Relation Age Play
Will you kiss after your partner has gone down on you? Swallow or spit semen?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
5- Have you ever been hypnotized? Would you allow yourself to be?
19~ Who/when was your first “heartbreak”?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How many times do you think you have “made love”?
What is your favorite position? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you have a favorite? Is it ok if your partner does?
33- If you could visit any time period, when would you pick? Please explain why?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
(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…)
9~ How many times over your lifetime do you think you have had sex so far?
The Ice Breaker Questions
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?
37- Do you like your name? If you could change it, what would you change it too?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
30~ What's something unexpected that turns you on?
49~ How many times have you been married? Why did they end?
60~ How important is oral sex? Do you like receiving? Do you like giving?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you like the “69” position? Do you prefer to be on top or bottom?
7- What if a person smells a certain way? 8- How about smoking?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Repairman/Lonely Wife Virgin/Experienced
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
48~ Do you have any siblings? Are you close to your family?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
29- How superstitious are you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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…
36- Do you play video games? What is your favorite? Do you a least favorite?
Does the thought excite you? Care to share?
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?
81~ Do you have any kinks and/or fetishes?
20- What’s your favorite candy? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
2- What’s your favorite color? Do you a least favorite?
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)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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 you lose, are you willing to be their sex slave for a day, (anything goes)?
Over time has your thoughts on sex changed?
If YES, was it with 2 men or 2 women? Did you enjoy it?
12- What’s your favorite food? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
15- What's your favorite saying? What word or phrase is your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
6- Do you have dreams? Can you remember them? What do you usually dream about?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Do you watch it? What is your favorite?
Nurse/Patient Celebrity/Fan
4- For a pet, Cat, dog or other?
21~ What was the best date you ever went on? What has been the worst?
*** Random Questions ***
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
*** Deal Breaker Questions ***
10- What is your favorite family tradition? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
62~ Have you used adult toys?
Would /have you ever given your partner a lap dance and Striptease?
Nothing too Serious
Doctor/Nurse Stripper/Client
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
48~ Have you ever paid or been paid for sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
14- What's your favorite dessert? Do you a least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
11- List at least 5 things on your bucket list. Have you done any of them already?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
50~ How many children do you have? What are their ages?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
What is your favorite toy? Ever wanted to try a specific toy?
How well do you know me? And some of your thoughts about me
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
31- If given a chance to be immortal, would you take it? Why?
25~ How do you feel about PDA? (Public Display of Affection)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
92~ Have you ever had or have an STD? How many? What was it?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
47~ What would be your dream job and why?
51~ Are you willing to play adult games with your partner?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would you allow me to clean every part of your body with my soapy hands and fingers?
21- What's your favorite way to spend a weekend or time off?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
38~ Share your most embarrassing sexual memory?
33- Beach or Mountains? Or is there another place to like better?
39~ What are your love languages?
29~ What are some things that turn you off? What is your biggest turn off?
Do you think this brought you closer together?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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?
If yes, what?
19- Do/have you smoked? What do you prefer? How often?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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?
13- What’s your favorite drink? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
34- Ever been to a concert? What was your favorite? Who would you like to see?
5~ When you first started having sex, was it what you thought it would be?
40~ What’s the weirdest place you’ve ever had sex?
Please share Did you stop?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
9- What’s your favorite season and why? What’s your least favorite?
* Give a rating for each one (0-100)
3- Should Pluto still be considered a planet? 4- How about smoking?
13- How about having a certain hair cut/style?
34~ Do you like the lights on or off during sex?
12- What is the weirdest thing you've ever eaten?
3- What’s your favorite smell? Do you a least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How about if they talk dirty and/or call you names?
Would you ever want to be woken up with oral and/or intercourse?
10~ How many dates are necessary before you to have sex with someone?
36~ What is your favorite time of day to have sex/make love?
Any that are a turn off?
18- How often do you drink alcohol? What is your favorite drink?
How old are you? Male or Female?
42~ What’s your biggest regret in life?
89~ Do you like taking showers together?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
61~ How willing would you be to try new sexual positions?
What is your view on sex? Meaning, When/Where/ How often/
Get this wrong and this could mean the end… :-) some funny, some not…
52~ Are you willing to make “those types” of bets with your partner?
9- Is there something you’ve always wanted to ask me but you’re afraid?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
11- What's your favorite restaurant? What’s your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
*** Questions About Me ***
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Escort/Client Job Applicant/Hiring Manager
26~ What side of the bed do you sleep on?
Would you do it again, and would you rather 2 females or 2 males?
83~ How do you feel about Porn?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
17- What’s your favorite holiday? What’s your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
19- What’s your favorite fairytale? What’s your least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
7-What do I do in bed that drives you wild? How about, what turns you off?
Will you cheat again? How can, you be sure? Define what cheating is to you.
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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.
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
15- What bad habit do you wish you could quit? Do you have any addictions?
52~ What are your hobbies?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What was the longest? What was the shortest?
8- What's your favorite flavor of ice cream? Do you a least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
28~ What are some things that turn on? What is your biggest turn on?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
I would allow you to do it… What would you do to me?
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,
8- What are your thoughts on politics?
10- List 5 of your top pet peeves.
13~ Is there a difference between, making love, having sex, and fucking?