What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 00:07
83~ How do you feel about Porn?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Nothing too Serious
What thing happened to you as a child that you haven’t let go of to this day?
60~ How important is oral sex? Do you like receiving? Do you like giving?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Why can't they repair the damage caused by Elon Musk renaming Twitter to X?
29~ What are some things that turn you off? What is your biggest turn off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
That one or two things that made you go hmmmm, OMG or wow!
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?
Have you ever? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How do empaths destroy narcissists?
19- Do/have you smoked? What do you prefer? How often?
3- Should Pluto still be considered a planet? 4- How about smoking?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Why are Indians so influenced by the Western culture, when the Indian tradition has so much to give?
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?
53~ How much can you tell me about the one thing you are most passionate about?
Why do some people tell the girl I like that I don’t like her when I do like her?
21- What's your favorite way to spend a weekend or time off?
7- What if a person smells a certain way? 8- How about smoking?
12- What is the weirdest thing you've ever eaten?
How much stronger is an average man than an average woman?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
48~ Do you have any siblings? Are you close to your family?
Do crossdressers like wearing pantyliners and tampons in their butts?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Escort/Client Job Applicant/Hiring Manager
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
49~ How many times have you been married? Why did they end?
11- List at least 5 things on your bucket list. Have you done any of them already?
12- What’s your favorite food? What’s your least favorite?
How do you confront your own family for not inviting you or leaving you out of things?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
61~ How willing would you be to try new sexual positions?
*** Random Questions ***
47~ What would be your dream job and why?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Would /have you ever given your partner a lap dance and Striptease?
36- Do you play video games? What is your favorite? Do you a least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Please share Did you stop?
14- What is an embarrassing moment in your life? How about your most embarrassing?
92~ Everyone needs a “safe” word. What is yours?
Will you cheat again? How can, you be sure? Define what cheating is to you.
7- What are your thoughts on religion? Is there an afterlife?
I would allow you to do it… What would you do to me?
Any that are a turn off?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
26~ What side of the bed do you sleep on?
7-What do I do in bed that drives you wild? How about, what turns you off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Doctor/Nurse Stripper/Client
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
23- What is your dream job? What was it as a child?
Model/Photographer Police/Criminal
15- What bad habit do you wish you could quit? Do you have any addictions?
17- Have you ever done drugs? Which ones? How often?
45~ How do you feel about me blindfolding you? How about blindfolding me?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
18~ Who/when was your first “crush”?
82~ Do you have any fantasies involving Role-Playing?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
13- What’s your favorite drink? What’s your least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Master/Slave Boss/Maid
If you win, what will you make them do?
Would you read them together?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
If yes, what?
9- What’s your favorite season and why? What’s your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you like it when they show and tell you what they want?
3- What’s your favorite smell? Do you a least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
14- What's your favorite dessert? Do you a least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
13~ Is there a difference between, making love, having sex, and fucking?
28- What are some things that people do that irritate you?
(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…)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
28~ What are some things that turn on? What is your biggest turn on?
5~ When you first started having sex, was it what you thought it would be?
52~ What are your hobbies?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What would you say to prove to yourself that it was really you?
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
1~ How old were you when you had your first kiss? Who? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
Do you think this brought you closer together?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
1- What’s your favorite animal? Do you a least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
How many times do you think you have “made love”?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
1- What was your first impression of me? Has it changed?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
What is your favorite toy? Ever wanted to try a specific toy?
17- What’s your favorite holiday? What’s your least favorite?
* Give a rating for each one (0-100)
39~ What are your love languages?
Would you do it again, and would you rather 2 females or 2 males?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
*** What’s Your Favorite…? ***
How well do you know me? And some of your thoughts about me
64~ When was your very first orgasm? When was your first from having sex? Care to share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Family Relation Age Play
Repairman/Lonely Wife Virgin/Experienced
34~ Do you like the lights on or off during sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
20- What’s your favorite candy? What’s your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Does the thought excite you? Care to share?
51~ Are you willing to play adult games with your partner?
50~ How many children do you have? What are their ages?
89~ Do you like taking showers together?
11- What's your favorite restaurant? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
10~ How many dates are necessary before you to have sex with someone?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
9- If you could have three wishes, what would they be? Why?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
What is your favorite position? Why?
22- What is your favorite childhood memory? What is your least favorite?
What was the longest? What was the shortest?
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)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
48~ Have you ever paid or been paid for sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
10- List 5 of your top pet peeves.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
44~ Care to share something about yourself that no one else knows about you?
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…
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…
9- Is there something you’ve always wanted to ask me but you’re afraid?
Can you Deep Throat? Do you like the taste of yourself?
10- What is your favorite family tradition? What’s your least favorite?
51~ What tends to bring a smile to your face?
*** Questions About Me ***
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
67~ Do you like it when your partner moans and/or is vocal during sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What do you dislike about me? I asked you to be 100% honest.
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?
38~ Share your most embarrassing sexual memory?
Get this wrong and this could mean the end… :-) some funny, some not…
What is your view on sex? Meaning, When/Where/ How often/
Prisoner/Prison Guard Landlord/Tenant
5- Have you ever been hypnotized? Would you allow yourself to be?
37- Do you like your name? If you could change it, what would you change it too?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
52~ Are you willing to make “those types” of bets with your partner?
11~ Have you ever been caught by your parents or children or others while having sex?
62~ Have you used adult toys?
How about if they talk dirty and/or call you names?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
33- Beach or Mountains? Or is there another place to like better?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Do you like the “69” position? Do you prefer to be on top or bottom?
80~ Share your top three fantasies/desires. (Be detailed) 😊
27- What was/ is nickname? Does it have a meaning behind it?
*** Deal Breaker Questions ***
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
4- For a pet, Cat, dog or other?
81~ Do you have any kinks and/or fetishes?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
25~ How do you feel about PDA? (Public Display of Affection)
65~ Describe the best orgasm you’ve ever had? Care to share?
36~ What is your favorite time of day to have sex/make love?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would you ever want to be woken up with oral and/or intercourse?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
42~ What’s your biggest regret in life?
29- How superstitious are you?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
18- How often do you drink alcohol? What is your favorite drink?
71~ Would you give your partner a hand or foot job? Would you receive one?
What have you learned about yourself that you did not before this?
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?
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?
*** Questions about Relationships/Past ***
92~ Have you ever had or have an STD? How many? What was it?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Any that are a turn off?
2- What’s your favorite color? Do you a least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
You know that I will be 100% truthful, so ask.
15~ Have you ever been “in love”? Who? Care to Share?
Do you have a favorite? Is it ok if your partner does?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
8- What are your thoughts on politics?
Over time has your thoughts on sex changed?
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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
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,
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
70~ Would/do you have/like anal sex?
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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
13- How about having a certain hair cut/style?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
8- What's your favorite flavor of ice cream? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Teacher/Student Stranger/One Night Stand
15- What's your favorite saying? What word or phrase is your least favorite?
What have you learned about me that was new and/or surprising?
31- If given a chance to be immortal, would you take it? Why?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
The Ice Breaker Questions
40~ What’s the weirdest place you’ve ever had sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
33- If you could visit any time period, when would you pick? Please explain why?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Nurse/Patient Celebrity/Fan
How many partners have you had oral sex with? Who? Care to Share?
Do you watch it? What is your favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
* 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?
32- What's your greatest talent? Can I see it right now?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
34- Ever been to a concert? What was your favorite? Who would you like to see?
How old are you? Male or Female?
Would you mind if your partner watched it? How about together vs alone?
19~ Who/when was your first “heartbreak”?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
76~ Have you had a threesome? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
3- What Superhero or Superpower would you want to be/have?
If YES, was it with 2 men or 2 women? Did you enjoy it?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)