What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 00:50
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
14- What's your favorite dessert? Do you a least favorite?
Why is blood sugar ranging from 70-180 in a day and checked through a glucometer?
Prisoner/Prison Guard Landlord/Tenant
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
2- What’s your favorite color? Do you a least favorite?
What does it feel like wearing tights?
13- How about having a certain hair cut/style?
81~ Do you have any kinks and/or fetishes?
1- What was your first impression of me? Has it changed?
Why am I so tired of seeing homeless people all over the place?
39~ What are your love languages?
That one or two things that made you go hmmmm, OMG or wow!
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Kuorans, what are some things unique to your country?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Family Relation Age Play
Repairman/Lonely Wife Virgin/Experienced
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you think this brought you closer together?
52~ What are your hobbies?
Will you cheat again? How can, you be sure? Define what cheating is to you.
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Who is the most annoying character in the Office?
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 is your favorite toy? Ever wanted to try a specific toy?
3- Should Pluto still be considered a planet? 4- How about smoking?
If YES, was it with 2 men or 2 women? Did you enjoy it?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
10- What is your favorite family tradition? What’s your least favorite?
Trump Military Parade: Darcy cartoon - Cleveland.com
*** Questions About Me ***
Do you like it when they show and tell you what they want?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Are evolutionists giving evolution a bad name by claiming humans started off as shrews?
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Nurse/Patient Celebrity/Fan
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Master/Slave Boss/Maid
How many partners have you had oral sex with? Who? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
11~ Have you ever been caught by your parents or children or others while having sex?
Why do Indian parents force their kids to do stuff?
11- What's your favorite restaurant? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Would you mind if your partner watched it? How about together vs alone?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
38~ Share your most embarrassing sexual memory?
Over time has your thoughts on sex changed?
82~ Do you have any fantasies involving Role-Playing?
*** Random Questions ***
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What have you learned about me that was new and/or surprising?
37- Do you like your name? If you could change it, what would you change it too?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
How well do you know me? And some of your thoughts about me
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
*** What’s Your Favorite…? ***
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
46~ Have you ever used furniture, or other types of things to aid you while having sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5~ When you first started having sex, was it what you thought it would be?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
11- How about if they like a certain sports team? 12-How about drinking too much?
89~ Do you like taking showers together?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
17- Have you ever done drugs? Which ones? How often?
What was the longest? What was the shortest?
7-What do I do in bed that drives you wild? How about, what turns you off?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What is your view on sex? Meaning, When/Where/ How often/
51~ Are you willing to play adult games with your partner?
32- What's your greatest talent? Can I see it right now?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Would you ever want to be woken up with oral and/or intercourse?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
13- What’s your favorite drink? What’s your least favorite?
You know that I will be 100% truthful, so ask.
9- What’s your favorite season and why? What’s your least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
13~ Is there a difference between, making love, having sex, and fucking?
21~ What was the best date you ever went on? What has been the worst?
3- What Superhero or Superpower would you want to be/have?
Nothing too Serious
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
* Give a rating for each one (0-100)
22- Do you have any birth marks? How about scars? Care to share how you got them?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
70~ Would/do you have/like anal sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
12- What is the weirdest thing you've ever eaten?
1- What’s your favorite animal? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
34~ Do you like the lights on or off during 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?
13- What is the craziest/scariest thing you've ever done?
71~ Would you give your partner a hand or foot job? Would you receive one?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
17- What’s your favorite holiday? What’s your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
10- List 5 of your top pet peeves.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
48~ Do you have any siblings? Are you close to your family?
How many times do you think you have “made love”?
12- What’s your favorite food? What’s your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Do you like the “69” position? Do you prefer to be on top or bottom?
8- What are your thoughts on politics?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
40~ What’s the weirdest place you’ve ever had sex?
Would you do it again, and would you rather 2 females or 2 males?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
29- How superstitious are you?
83~ How do you feel about Porn?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
44~ Care to share something about yourself that no one else knows about you?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
49~ How many times have you been married? Why did they end?
Any that are a turn off?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
48~ Have you ever paid or been paid for sex?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
7- What if a person smells a certain way? 8- How about smoking?
61~ How willing would you be to try new sexual positions?
What is your favorite position? Why?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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?
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)
Any that are a turn off?
9- If you could have three wishes, what would they be? Why?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
Escort/Client Job Applicant/Hiring Manager
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
60~ How important is oral sex? Do you like receiving? Do you like giving?
28~ What are some things that turn on? What is your biggest turn on?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
*** Deal Breaker Questions ***
Please share Did you stop?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
15- What bad habit do you wish you could quit? Do you have any addictions?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
50~ How many children do you have? What are their ages?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
52~ Are you willing to make “those types” of bets with your partner?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What do you dislike about me? I asked you to be 100% honest.
15~ Have you ever been “in love”? Who? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
I would allow you to do it… What would you do to me?
If yes, what?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
How old are you? Male or Female?
4- For a pet, Cat, dog or other?
Can you Deep Throat? Do you like the taste of yourself?
42~ What’s your biggest regret in life?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
36~ What is your favorite time of day to have sex/make love?
30~ What's something unexpected that turns you on?
9~ How many times over your lifetime do you think you have had sex so far?
84~ How do you feel about reading/listening to adult stories?
33- Beach or Mountains? Or is there another place to like better?
76~ Have you had a threesome? Care to Share?
What have you learned about yourself that you did not before this?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
53~ How much can you tell me about the one thing you are most passionate about?
26~ What side of the bed do you sleep on?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Doctor/Nurse Stripper/Client
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
27- What was/ is nickname? Does it have a meaning behind it?
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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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,
67~ Do you like it when your partner moans and/or is vocal during sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
34- Ever been to a concert? What was your favorite? Who would you like to see?
31- If given a chance to be immortal, would you take it? Why?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Does the thought excite you? Care to share?
10~ How many dates are necessary before you to have sex with someone?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
The Ice Breaker Questions
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Get this wrong and this could mean the end… :-) some funny, some not…
18~ Who/when was your first “crush”?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
47~ What would be your dream job and why?
What would you say to prove to yourself that it was really you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
21- What's your favorite way to spend a weekend or time off?
Teacher/Student Stranger/One Night Stand
22- What is your favorite childhood memory? What is your least favorite?
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Do you watch it? What is your favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
15- What's your favorite saying? What word or phrase is your least favorite?
Do you have a favorite? Is it ok if your partner does?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
7- What are your thoughts on religion? Is there an afterlife?
62~ Have you used adult toys?
23- What is your dream job? What was it as a child?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Would /have you ever given your partner a lap dance and Striptease?
Model/Photographer Police/Criminal
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
28- What are some things that people do that irritate you?
20- What’s your favorite candy? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
*** Questions about Relationships/Past ***
51~ What tends to bring a smile to your face?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
80~ Share your top three fantasies/desires. (Be detailed) 😊
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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…
25~ How do you feel about PDA? (Public Display of Affection)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
(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…)
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?
Have you ever? Care to Share?
How about if they talk dirty and/or call you names?
If you win, what will you make them do?
If NO, would you ever have one? Would it be with 2 men or 2 women?
19~ Who/when was your first “heartbreak”?
Would you read them together?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
65~ Describe the best orgasm you’ve ever had? Care to share?