What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 00:03
Master/Slave Boss/Maid
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
76~ Have you had a threesome? Care to Share?
Would the word literate carry the same meaning with public (common wealth) in 1900 vs today 2020?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
36- Do you play video games? What is your favorite? Do you a least favorite?
*** Questions About Me ***
What are the ten cars that make me no longer feel inferior?
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3- What’s your favorite smell? Do you a least favorite?
30~ What's something unexpected that turns you on?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
23- What is your dream job? What was it as a child?
13- What is the craziest/scariest thing you've ever done?
9~ How many times over your lifetime do you think you have had sex so far?
Why won't my mom let me come home if I'm homeless?
How many times do you think you have “made love”?
How old are you? Male or Female?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Have you ever accidentally found out that you were about to be fired?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
47~ What would be your dream job and why?
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What happened to your school bully?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
37- Do you like your name? If you could change it, what would you change it too?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What are some photos of female sexual organs?
19- What’s your favorite fairytale? What’s your least favorite?
4- For a pet, Cat, dog or other?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
What ended your relationship with your best friend?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
67~ Do you like it when your partner moans and/or is vocal during sex?
Why are Americans obese? Is it the food or is it the psychology?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
32- What's your greatest talent? Can I see it right now?
If you say it, I will stop, and we can talk about it when you are ready.
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?
*** What’s Your Favorite…? ***
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How well do you know me? And some of your thoughts about 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,
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Can you Deep Throat? Do you like the taste of yourself?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How about if they talk dirty and/or call you names?
81~ Do you have any kinks and/or fetishes?
17- Have you ever done drugs? Which ones? How often?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
Repairman/Lonely Wife Virgin/Experienced
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
33- If you could visit any time period, when would you pick? Please explain why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
If you win, what will you make them do?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
*** Questions about Relationships/Past ***
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
20- What’s your favorite candy? What’s your least favorite?
19~ Who/when was your first “heartbreak”?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
15- What's your favorite saying? What word or phrase is your least favorite?
1- What’s your favorite animal? Do you a least favorite?
12- What is the weirdest thing you've ever eaten?
*** Random Questions ***
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
62~ Have you used adult toys?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Any that are a turn off?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
70~ Would/do you have/like anal sex?
15~ Have you ever been “in love”? Who? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
42~ What’s your biggest regret in life?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
11- How about if they like a certain sports team? 12-How about drinking too much?
Any that are a turn off?
17- What’s your favorite holiday? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
1~ How old were you when you had your first kiss? Who? Care to Share?
51~ What tends to bring a smile to your face?
Would you ever want to be woken up with oral and/or intercourse?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
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?
84~ How do you feel about reading/listening to adult stories?
Have you ever? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Doctor/Nurse Stripper/Client
Nothing too Serious
5~ When you first started having sex, was it what you thought it would be?
Does the thought excite you? Care to share?
71~ Would you give your partner a hand or foot job? Would you receive one?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
3- Should Pluto still be considered a planet? 4- How about smoking?
Would you read them together?
How many partners have you had oral sex with? Who? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
2- What’s your favorite color? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Nurse/Patient Celebrity/Fan
21~ What was the best date you ever went on? What has been the worst?
27- What was/ is nickname? Does it have a meaning behind it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
You know that I will be 100% truthful, so ask.
Teacher/Student Stranger/One Night Stand
What have you learned about me that was new and/or surprising?
25~ How do you feel about PDA? (Public Display of Affection)
Escort/Client Job Applicant/Hiring Manager
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
(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…)
52~ Are you willing to make “those types” of bets with your partner?
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?
50~ How many children do you have? What are their ages?
34~ Do you like the lights on or off during sex?
33- Beach or Mountains? Or is there another place to like better?
21- Do you have any piercings? 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?
Get this wrong and this could mean the end… :-) some funny, some not…
7- What are your thoughts on religion? Is there an afterlife?
Model/Photographer Police/Criminal
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
Over time has your thoughts on sex changed?
92~ Everyone needs a “safe” word. What is yours?
22- Do you have any birth marks? How about scars? Care to share how you got them?
That one or two things that made you go hmmmm, OMG or wow!
Do you think this brought you closer together?
51~ Are you willing to play adult games with your partner?
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What would you say to prove to yourself that it was really you?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What was the longest? What was the shortest?
29~ What are some things that turn you off? What is your biggest turn off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
40~ What’s the weirdest place you’ve ever had sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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)
65~ Describe the best orgasm you’ve ever had? Care to share?
21- What's your favorite way to spend a weekend or time off?
39~ What are your love languages?
If yes, what?
13- What’s your favorite drink? What’s your least favorite?
Do you watch it? What is your favorite?
48~ Have you ever paid or been paid for sex?
What have you learned about yourself that you did not before this?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
28~ What are some things that turn on? What is your biggest turn on?
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?
44~ Care to share something about yourself that no one else knows about you?
26~ What side of the bed do you sleep on?
Do you like it when they show and tell you what they want?
12- What’s your favorite food? What’s your least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
9- If you could have three wishes, what would they be? Why?
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.
*** Deal Breaker Questions ***
* Give a rating for each one (0-100)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Family Relation Age Play
9- What’s your favorite season and why? What’s your least favorite?
10~ How many dates are necessary before you to have sex with someone?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Will you cheat again? How can, you be sure? Define what cheating is to you.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
8- What are your thoughts on politics?
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…
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
34- Ever been to a concert? What was your favorite? Who would you like to see?
What do you dislike about me? I asked you to be 100% honest.
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?
7- What if a person smells a certain way? 8- How about smoking?
Would /have you ever given your partner a lap dance and Striptease?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
89~ Do you like taking showers together?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
11- List at least 5 things on your bucket list. Have you done any of them already?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
11- What's your favorite restaurant? What’s your least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
52~ What are your hobbies?
19- Do/have you smoked? What do you prefer? How often?
18~ Who/when was your first “crush”?
13- How about having a certain hair cut/style?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Please share Did you stop?
Do you like the “69” position? Do you prefer to be on top or bottom?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Do you have a favorite? Is it ok if your partner does?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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)
14- What's your favorite dessert? Do you a least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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…
10- List 5 of your top pet peeves.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What is your favorite position? Why?
38~ Share your most embarrassing sexual memory?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
80~ Share your top three fantasies/desires. (Be detailed) 😊
6- Do you have dreams? Can you remember them? What do you usually dream about?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
11~ Have you ever been caught by your parents or children or others while having sex?
Would you mind if your partner watched it? How about together vs alone?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
29- How superstitious are you?
The Ice Breaker Questions
I would allow you to do it… What would you do to me?
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?
53~ How much can you tell me about the one thing you are most passionate about?
61~ How willing would you be to try new sexual positions?
28- What are some things that people do that irritate you?
Would you do it again, and would you rather 2 females or 2 males?
5- Have you ever been hypnotized? Would you allow yourself to be?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What is your view on sex? Meaning, When/Where/ How often/
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
15- What bad habit do you wish you could quit? Do you have any addictions?
Prisoner/Prison Guard Landlord/Tenant
10- What is your favorite family tradition? What’s your least favorite?
49~ How many times have you been married? Why did they end?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
1- What was your first impression of me? Has it changed?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.