What is the most interesting question you can ask to get to know someone?
Last Updated: 22.06.2025 13:46
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
48~ Do you have any siblings? Are you close to your family?
*** Random Questions ***
What are some photos of female sexual organs?
7-What do I do in bed that drives you wild? How about, what turns you off?
82~ Do you have any fantasies involving Role-Playing?
3- What Superhero or Superpower would you want to be/have?
22- Do you have any birth marks? How about scars? Care to share how you got them?
11- How about if they like a certain sports team? 12-How about drinking too much?
If you win, what will you make them do?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If NO, would you ever have one? Would it be with 2 men or 2 women?
10~ How many dates are necessary before you to have sex with someone?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
80~ Share your top three fantasies/desires. (Be detailed) đ
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If you say it, I will stop, and we can talk about it when you are ready.
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
81~ Do you have any kinks and/or fetishes?
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51~ What tends to bring a smile to your face?
28- What are some things that people do that irritate you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Repairman/Lonely Wife Virgin/Experienced
10- List 5 of your top pet peeves.
Please share Did you stop?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
I dreamt my mother had died and I cried so much in my dream. What does it mean?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
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Nothing too Serious
* Give a rating for each one (0-100)
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?
In the TV show Supernatural, why is God portrayed as cruel?
92~ Everyone needs a âsafeâ word. What is yours?
Any that are a turn off?
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 togetherâŚ
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Would you mind if your partner watched it? How about together vs alone?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
52~ What are your hobbies?
If yes, what?
What is your favorite toy? Ever wanted to try a specific toy?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
61~ How willing would you be to try new sexual positions?
Do you think this brought you closer together?
33- If you could visit any time period, when would you pick? Please explain why?
29- How superstitious are you?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
3- Whatâs your favorite smell? Do you a least favorite?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
What do you dislike about me? I asked you to be 100% honest.
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
9- Is there something youâve always wanted to ask me but youâre afraid?
33- Beach or Mountains? Or is there another place to like better?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What if a person smells a certain way? 8- How about smoking?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
I would allow you to do it⌠What would you do to me?
Family Relation Age Play
*** Deal Breaker Questions ***
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
5~ When you first started having sex, was it what you thought it would be?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
The Ice Breaker Questions
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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? Donât be shy now, I really want to know.
14- What's your favorite dessert? Do you a least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you watch it? What is your favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
84~ How do you feel about reading/listening to adult stories?
Would you ever want to be woken up with oral and/or intercourse?
19~ Who/when was your first âheartbreakâ?
Can you Deep Throat? Do you like the taste of yourself?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
7- What are your thoughts on religion? Is there an afterlife?
What was the longest? What was the shortest?
Escort/Client Job Applicant/Hiring Manager
6- Do you have dreams? Can you remember them? What do you usually dream about?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- What was the most surprising thing youâve learned about me throughout our relationship?
22- What is your favorite childhood memory? What is your least favorite?
83~ How do you feel about Porn?
37- Do you like your name? If you could change it, what would you change it too?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
How about if they talk dirty and/or call you names?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
11- List at least 5 things on your bucket list. Have you done any of them already?
3- Should Pluto still be considered a planet? 4- How about smoking?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
34- Ever been to a concert? What was your favorite? Who would you like to see?
17- Have you ever done drugs? Which ones? How often?
Master/Slave Boss/Maid
39~ What are your love languages?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What have you learned about yourself that you did not before this?
9- If you could have three wishes, what would they be? Why?
That one or two things that made you go hmmmm, OMG or wow!
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
42~ Whatâs your biggest regret in life?
32- What's your greatest talent? Can I see it right now?
Teacher/Student Stranger/One Night Stand
Any that are a turn off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Do you like the â69â position? Do you prefer to be on top or bottom?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Model/Photographer Police/Criminal
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
25~ How do you feel about PDA? (Public Display of Affection)
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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
2- Whatâs your favorite color? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
19- Do/have you smoked? What do you prefer? How often?
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?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
*** Questions About Me ***
89~ Do you like taking showers together?
52~ Are you willing to make âthose typesâ of bets with your partner?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
53~ How much can you tell me about the one thing you are most passionate about?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Do you like it when they show and tell you what they want?
70~ Would/do you have/like anal sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
8- What are your thoughts on politics?
5- Have you ever been hypnotized? Would you allow yourself to be?
15- What's your favorite saying? What word or phrase is your least favorite?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
36- Do you play video games? What is your favorite? Do you a least favorite?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
4- For a pet, Cat, dog or other?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
13~ Is there a difference between, making love, having sex, and fucking?
13- Whatâs your favorite drink? Whatâs your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
28~ What are some things that turn on? What is your biggest turn on?
10- What is your favorite family tradition? Whatâs your least favorite?
76~ Have you had a threesome? Care to Share?
36~ What is your favorite time of day to have sex/make love?
Would /have you ever given your partner a lap dance and Striptease?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Do you have a favorite? Is it ok if your partner does?
Over time has your thoughts on sex changed?
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)
18- How often do you drink alcohol? What is your favorite drink?
21~ What was the best date you ever went on? What has been the worst?
50~ How many children do you have? What are their ages?
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
What would you say to prove to yourself that it was really you?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
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 âPASSâ 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 yourselfâŚ
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?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
30~ What's something unexpected that turns you on?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
38~ Share your most embarrassing sexual memory?
13- What is the craziest/scariest thing you've ever done?
How well do you know me? And some of your thoughts about me
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What was your first impression of me? Has it changed?
12- Whatâs your favorite food? Whatâs your least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
You know that I will be 100% truthful, so ask.
26~ What side of the bed do you sleep on?
15- What bad habit do you wish you could quit? Do you have any addictions?
If YES, was it with 2 men or 2 women? Did you enjoy it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
34~ Do you like the lights on or off during sex?
How old are you? Male or Female?
1~ How old were you when you had your first kiss? Who? Care to Share?
18~ Who/when was your first âcrushâ?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
48~ Have you ever paid or been paid for sex?
What have you learned about me that was new and/or surprising?
62~ Have you used adult toys?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How many times do you think you have âmade loveâ?
Does the thought excite you? Care to share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
*** Whatâs Your FavoriteâŚ? ***
67~ Do you like it when your partner moans and/or is vocal during sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
13- How about having a certain hair cut/style?
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
23- What is your dream job? What was it as a child?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
1- Whatâs your favorite animal? Do you a least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
9~ How many times over your lifetime do you think you have had sex so far?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Would you do it again, and would you rather 2 females or 2 males?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
51~ Are you willing to play adult games with your partner?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŚ)
47~ What would be your dream job and why?
Would you read them together?
20- Whatâs your favorite candy? Whatâs your least favorite?
Doctor/Nurse Stripper/Client
*** Questions about Relationships/Past ***
27- What was/ is nickname? Does it have a meaning behind it?
44~ Care to share something about yourself that no one else knows about you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How many partners have you had oral sex with? Who? Care to Share?
21- What's your favorite way to spend a weekend or time off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
8- What's your favorite flavor of ice cream? Do you a least favorite?
15~ Have you ever been âin loveâ? Who? Care to Share?
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
17- Whatâs your favorite holiday? Whatâs your least favorite?
65~ Describe the best orgasm youâve ever had? Care to share?
29~ What are some things that turn you off? What is your biggest turn off?
Nurse/Patient Celebrity/Fan
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
11- What's your favorite restaurant? Whatâs your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
12- What is the weirdest thing you've ever eaten?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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~ How many times a week would you like to engage in sexual activities? What is the average for you now?
9- Whatâs your favorite season and why? Whatâs your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
40~ Whatâs the weirdest place youâve ever had sex?
Have you ever? Care to Share?