What is the most interesting question you can ask to get to know someone?
10.06.2025 12:08
Teacher/Student Stranger/One Night Stand
44~ Care to share something about yourself that no one else knows about you?
Can you Deep Throat? Do you like the taste of yourself?
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16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Escort/Client Job Applicant/Hiring Manager
Would /have you ever given your partner a lap dance and Striptease?
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68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
29~ What are some things that turn you off? What is your biggest turn off?
92~ Have you ever had or have an STD? How many? What was it?
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If yes, what?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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…
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18~ Who/when was your first “crush”?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
76~ Have you had a threesome? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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,
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51~ What tends to bring a smile to your face?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
70~ Would/do you have/like anal sex?
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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Do all armies have the same rank structure?
6- Do you have dreams? Can you remember them? What do you usually dream about?
7- What if a person smells a certain way? 8- How about smoking?
What have you learned about me that was new and/or surprising?
How do you write lyrics for a song that resonates with listeners?
*** Questions about Relationships/Past ***
29- How superstitious are you?
If you say it, I will stop, and we can talk about it when you are ready.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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65~ Describe the best orgasm you’ve ever had? Care to share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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10- List 5 of your top pet peeves.
Master/Slave Boss/Maid
Prisoner/Prison Guard Landlord/Tenant
60 years ago, Ed White went out for walk photo of the day for June 3, 2025 - Space
4- For a pet, Cat, dog or other?
33- Beach or Mountains? Or is there another place to like better?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
8- What's your favorite flavor of ice cream? Do you a least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
What have you learned about yourself that you did not before this?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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Family Relation Age Play
39~ What are your love languages?
What would you say to prove to yourself that it was really you?
10~ How many dates are necessary before you to have sex with someone?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
80~ Share your top three fantasies/desires. (Be detailed) 😊
15- What bad habit do you wish you could quit? Do you have any addictions?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
33- If you could visit any time period, when would you pick? Please explain why?
*** What’s Your Favorite…? ***
64~ When was your very first orgasm? When was your first from having sex? Care to share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
48~ Do you have any siblings? Are you close to your family?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
9- If you could have three wishes, what would they be? Why?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
21~ What was the best date you ever went on? What has been the worst?
13- What is the craziest/scariest thing you've ever done?
Would you read them together?
50~ How many children do you have? What are their ages?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
7- What are your thoughts on religion? Is there an afterlife?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Model/Photographer Police/Criminal
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
36~ What is your favorite time of day to have sex/make love?
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?
I would allow you to do it… What would you do to me?
37- Do you like your name? If you could change it, what would you change it too?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
40~ What’s the weirdest place you’ve ever had sex?
28~ What are some things that turn on? What is your biggest turn on?
47~ What would be your dream job and why?
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
12- What’s your favorite food? What’s your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
38~ Share your most embarrassing sexual memory?
How about if they talk dirty and/or call you names?
17- Have you ever done drugs? Which ones? How often?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How old are you? Male or Female?
If YES, was it with 2 men or 2 women? Did you enjoy it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
61~ How willing would you be to try new sexual positions?
45~ How do you feel about me blindfolding you? How about blindfolding me?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
8- What are your thoughts on politics?
If NO, would you ever have one? Would it be with 2 men or 2 women?
11~ Have you ever been caught by your parents or children or others while having sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
11- What's your favorite restaurant? What’s your least favorite?
Any that are a turn off?
13~ Is there a difference between, making love, having sex, and fucking?
34~ Do you like the lights on or off during sex?
What is your favorite toy? Ever wanted to try a specific toy?
5- Have you ever been hypnotized? Would you allow yourself to be?
Have you ever? Care to Share?
Do you think this brought you closer together?
28- What are some things that people do that irritate you?
11- How about if they like a certain sports team? 12-How about drinking too much?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
81~ Do you have any kinks and/or fetishes?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What is your favorite position? Why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you like the “69” position? Do you prefer to be on top or bottom?
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)
14- What is an embarrassing moment in your life? How about your most embarrassing?
31- If given a chance to be immortal, would you take it? Why?
52~ Are you willing to make “those types” of bets with your partner?
5~ When you first started having sex, was it what you thought it would be?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
27- What was/ is nickname? Does it have a meaning behind it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
52~ What are your hobbies?
25~ How do you feel about PDA? (Public Display of Affection)
15~ Have you ever been “in love”? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
7-What do I do in bed that drives you wild? How about, what turns you off?
62~ Have you used adult toys?
42~ What’s your biggest regret in life?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
1~ How old were you when you had your first kiss? Who? Care to Share?
32- What's your greatest talent? Can I see it right now?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
23- What is your dream job? What was it as a child?
14- What's your favorite dessert? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
18- How often do you drink alcohol? What is your favorite drink?
20- What’s your favorite candy? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
53~ How much can you tell me about the one thing you are most passionate about?
*** Random Questions ***
84~ How do you feel about reading/listening to adult stories?
Get this wrong and this could mean the end… :-) some funny, some not…
34- Ever been to a concert? What was your favorite? Who would you like to see?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
89~ Do you like taking showers together?
That one or two things that made you go hmmmm, OMG or wow!
22- Do you have any birth marks? How about scars? Care to share how you got them?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Repairman/Lonely Wife Virgin/Experienced
Do you have a favorite? Is it ok if your partner does?
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?
Do you watch it? What is your favorite?
Would you mind if your partner watched it? How about together vs alone?
What was the longest? What was the shortest?
3- What Superhero or Superpower would you want to be/have?
36- Do you play video games? What is your favorite? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
51~ Are you willing to play adult games with your partner?
Nothing too Serious
19- Do/have you smoked? What do you prefer? How often?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Any that are a turn off?
9~ How many times over your lifetime do you think you have had sex so far?
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?
Would you ever want to be woken up with oral and/or intercourse?
What is your view on sex? Meaning, When/Where/ How often/
67~ Do you like it when your partner moans and/or is vocal during sex?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Over time has your thoughts on sex changed?
19~ Who/when was your first “heartbreak”?
17- What’s your favorite holiday? What’s your least favorite?
Please share Did you stop?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What do you dislike about me? I asked you to be 100% honest.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
30~ What's something unexpected that turns you on?
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Does the thought excite you? Care to share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How many times do you think you have “made love”?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
* Give a rating for each one (0-100)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
3- What’s your favorite smell? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
49~ How many times have you been married? Why did they end?
82~ Do you have any fantasies involving Role-Playing?
If you win, what will you make them do?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you do it again, and would you rather 2 females or 2 males?
92~ Everyone needs a “safe” word. What is yours?
13- What’s your favorite drink? What’s your least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
2- What’s your favorite color? 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?
1- What was your first impression of me? Has it changed?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
12- What is the weirdest thing you've ever eaten?
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?
13- How about having a certain hair cut/style?
The Ice Breaker Questions
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?
Doctor/Nurse Stripper/Client
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
10- What is your favorite family tradition? What’s your 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?
How well do you know me? And some of your thoughts about me
19- What’s your favorite fairytale? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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
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…
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
*** Deal Breaker Questions ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
You know that I will be 100% truthful, so ask.
How many partners have you had oral sex with? Who? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
(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…)
1- What’s your favorite animal? Do you a least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
83~ How do you feel about Porn?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?