What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 00:49
82~ Do you have any fantasies involving Role-Playing?
(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…)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What is it like to be the slave in a mistress-slave relationship?
Master/Slave Boss/Maid
40~ What’s the weirdest place you’ve ever had sex?
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…
Why does my private parts itch so much during certain periods?
13~ Is there a difference between, making love, having sex, and fucking?
23- What is your dream job? What was it as a child?
Prisoner/Prison Guard Landlord/Tenant
Have you ever been physically attacked by a demon?
29- How superstitious are you?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Would you do it again, and would you rather 2 females or 2 males?
Why do men cheat on their wives with someone extremely unattractive?
38~ Share your most embarrassing sexual memory?
47~ What would be your dream job and why?
15~ Have you ever been “in love”? Who? Care to Share?
What do you typically do while on meth?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
21- What's your favorite way to spend a weekend or time off?
5- Have you ever been hypnotized? Would you allow yourself to be?
What are the best examples of reverse psychology?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
13- How about having a certain hair cut/style?
9- What’s your favorite season and why? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
19~ Who/when was your first “heartbreak”?
*** Random Questions ***
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
84~ How do you feel about reading/listening to adult stories?
Why am I so tired of the keto diet?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
8- What's your favorite flavor of ice cream? Do you a least favorite?
Why do men like women gold diggers?
61~ How willing would you be to try new sexual positions?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What is your favorite position? Why?
2- What’s your favorite color? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
50~ How many children do you have? What are their ages?
44~ Care to share something about yourself that no one else knows about you?
11- What's your favorite restaurant? What’s your least favorite?
What was your best revenge story?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What have you learned about me that was new and/or surprising?
9~ How many times over your lifetime do you think you have had sex so far?
30~ What's something unexpected that turns you on?
*** Questions About Me ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
51~ What tends to bring a smile to your face?
Doctor/Nurse Stripper/Client
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?
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,
42~ What’s your biggest regret in life?
How old are you? Male or Female?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
92~ Have you ever had or have an STD? How many? What was it?
32- What's your greatest talent? Can I see it right now?
14- What is an embarrassing moment in your life? How about your most embarrassing?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
6- Do you have dreams? Can you remember them? What do you usually dream about?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Family Relation Age Play
34- Ever been to a concert? What was your favorite? Who would you like to see?
21~ What was the best date you ever went on? What has been the worst?
11- List at least 5 things on your bucket list. Have you done any of them already?
62~ Have you used adult toys?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
12- What is the weirdest thing you've ever eaten?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Will you cheat again? How can, you be sure? Define what cheating is to you.
53~ How much can you tell me about the one thing you are most passionate about?
10- What is your favorite family tradition? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
1- What’s your favorite animal? Do you a least favorite?
Does the thought excite you? Care to share?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
11~ Have you ever been caught by your parents or children or others while having sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
20- What’s your favorite candy? What’s your least favorite?
1- What was your first impression of me? Has it changed?
Over time has your thoughts on sex changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
49~ How many times have you been married? Why did they end?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
28~ What are some things that turn on? What is your biggest turn on?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
If you win, what will you make them do?
Do you have a favorite? Is it ok if your partner does?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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)
*** What’s Your Favorite…? ***
What would you say to prove to yourself that it was really you?
Escort/Client Job Applicant/Hiring Manager
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? 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?
27- What was/ is nickname? Does it have a meaning behind it?
52~ What are your hobbies?
17- What’s your favorite holiday? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
22- Do you have any birth marks? How about scars? Care to share how you got them?
If you say it, I will stop, and we can talk about it when you are ready.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
29~ What are some things that turn you off? What is your biggest turn off?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
11- How about if they like a certain sports team? 12-How about drinking too much?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
31- If given a chance to be immortal, would you take it? Why?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
33- If you could visit any time period, when would you pick? Please explain why?
8- What are your thoughts on politics?
34~ Do you like the lights on or off during sex?
10- List 5 of your top pet peeves.
How many times do you think you have “made love”?
89~ Do you like taking showers together?
Please share Did you stop?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
That one or two things that made you go hmmmm, OMG or wow!
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
15- What bad habit do you wish you could quit? Do you have any addictions?
* Give a rating for each one (0-100)
The Ice Breaker Questions
26~ What side of the bed do you sleep on?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
76~ Have you had a threesome? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
25~ How do you feel about PDA? (Public Display of Affection)
13- What’s your favorite drink? What’s your least favorite?
Model/Photographer Police/Criminal
80~ Share your top three fantasies/desires. (Be detailed) 😊
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
How well do you know me? And some of your thoughts about me
52~ Are you willing to make “those types” of bets with your partner?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
33- Beach or Mountains? Or is there another place to like better?
Do you like it when they show and tell you what they want?
Would you read them together?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
92~ Everyone needs a “safe” word. What is yours?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What was the longest? What was the shortest?
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?
If yes, what?
Would you allow me to clean every part of your body with my soapy hands and fingers?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Would /have you ever given your partner a lap dance and Striptease?
39~ What are your love languages?
12- What’s your favorite food? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
Nothing too Serious
You know that I will be 100% truthful, so ask.
60~ How important is oral sex? Do you like receiving? Do you like giving?
28- What are some things that people do that irritate you?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Will you kiss after your partner has gone down on you? Swallow or spit semen?
How about if they talk dirty and/or call you names?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
19- Do/have you smoked? What do you prefer? How often?
What have you learned about yourself that you did not before this?
3- What’s your favorite smell? Do you a least favorite?
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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Any that are a turn off?
13- What is the craziest/scariest thing you've ever done?
7-What do I do in bed that drives you wild? How about, what turns you off?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Any that are a turn off?
10~ How many dates are necessary before you to have sex with someone?
70~ Would/do you have/like anal sex?
18~ Who/when was your first “crush”?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
14- What's your favorite dessert? Do you a least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Repairman/Lonely Wife Virgin/Experienced
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
How many partners have you had oral sex with? Who? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
9- Is there something you’ve always wanted to ask me but you’re afraid?
7- What are your thoughts on religion? Is there an afterlife?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
3- What Superhero or Superpower would you want to be/have?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What is your view on sex? Meaning, When/Where/ How often/
36- Do you play video games? What is your favorite? Do you a least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Have you ever? Care to Share?
Teacher/Student Stranger/One Night Stand
37- Do you like your name? If you could change it, what would you change it too?
*** Deal Breaker Questions ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
36~ What is your favorite time of day to have sex/make love?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
51~ Are you willing to play adult games with your partner?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
83~ How do you feel about Porn?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
What is your favorite toy? Ever wanted to try a specific toy?
Do you like the “69” position? Do you prefer to be on top or bottom?
48~ Do you have any siblings? Are you close to your family?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
81~ Do you have any kinks and/or fetishes?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
22- What is your favorite childhood memory? What is your least favorite?
Do you watch it? What is your favorite?
*** Questions about Relationships/Past ***
17- Have you ever done drugs? Which ones? How often?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you think this brought you closer together?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
67~ Do you like it when your partner moans and/or is vocal during sex?
Get this wrong and this could mean the end… :-) some funny, some not…
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
18- How often do you drink alcohol? What is your favorite drink?
What do you dislike about me? I asked you to be 100% honest.
If NO, would you ever have one? Would it be with 2 men or 2 women?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
65~ Describe the best orgasm you’ve ever had? Care to share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Nurse/Patient Celebrity/Fan
I would allow you to do it… What would you do to me?
9- If you could have three wishes, what would they be? Why?
Would you ever want to be woken up with oral and/or intercourse?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
48~ Have you ever paid or been paid for sex?
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…