What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 16:37
3- Should Pluto still be considered a planet? 4- How about smoking?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What sexual fantasies do you have?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
51~ What tends to bring a smile to your face?
Sean 'Diddy' Combs trial day 27 recap: Judge signals plans to remove a juror - ABC News
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
What does it mean when we dream about demons, ghosts, monsters, etc.?
3- What’s your favorite smell? Do you a least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Nurse/Patient Celebrity/Fan
80~ Share your top three fantasies/desires. (Be detailed) 😊
6- Do you have dreams? Can you remember them? What do you usually dream about?
48~ Do you have any siblings? Are you close to your family?
2- What’s your favorite color? Do you a 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?
Who is the most annoying character in the Office?
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?
53~ How much can you tell me about the one thing you are most passionate about?
33- Beach or Mountains? Or is there another place to like better?
What was your best experience of having your navel touched?
11- How about if they like a certain sports team? 12-How about drinking too much?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Is it true that schizophrenia can sometimes be a demonic attack or black magic?
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.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Why do men like to have sex with a woman's ass?
12- What’s your favorite food? What’s your least favorite?
1- What’s your favorite animal? Do you a least favorite?
(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…)
What is so great about Jiraiya?
81~ Do you have any kinks and/or fetishes?
Would you mind if your partner watched it? How about together vs alone?
13~ Is there a difference between, making love, having sex, and fucking?
Why do people still think Michael Jackson was guilty?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What is your view on sex? Meaning, When/Where/ How often/
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
31- If given a chance to be immortal, would you take it? Why?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
37- Do you like your name? If you could change it, what would you change it too?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
*** Random Questions ***
Have you ever? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How about if they talk dirty and/or call you names?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Do you like it when they show and tell you what they want?
92~ Everyone needs a “safe” word. What is yours?
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?
40~ What’s the weirdest place you’ve ever had sex?
Please share Did you stop?
22- What is your favorite childhood memory? What is your least favorite?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
If you win, what will you make them do?
*** What’s Your 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?
*** Questions About Me ***
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
8- What's your favorite flavor of ice cream? 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?
15- What's your favorite saying? What word or phrase is your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
36~ What is your favorite time of day to have sex/make love?
28- What are some things that people do that irritate you?
Family Relation Age Play
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
11- List at least 5 things on your bucket list. Have you done any of them already?
What is your favorite toy? Ever wanted to try a specific toy?
70~ Would/do you have/like anal sex?
8- What are your thoughts on politics?
Nothing too Serious
71~ Would you give your partner a hand or foot job? Would you receive one?
10- List 5 of your top pet peeves.
You know that I will be 100% truthful, so ask.
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
11~ Have you ever been caught by your parents or children or others while having sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What is your favorite position? Why?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
*** Questions about Relationships/Past ***
*** Deal Breaker Questions ***
Prisoner/Prison Guard Landlord/Tenant
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
51~ Are you willing to play adult games with your partner?
36- Do you play video games? What is your favorite? Do you a least favorite?
14- What's your favorite dessert? Do you a least favorite?
Doctor/Nurse Stripper/Client
How many times do you think you have “made love”?
Would you ever want to be woken up with oral and/or intercourse?
20- What’s your favorite candy? What’s your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you watch it? What is your favorite?
Would /have you ever given your partner a lap dance and Striptease?
12- What is the weirdest thing you've ever eaten?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
How old are you? Male or Female?
9- If you could have three wishes, what would they be? Why?
What do you dislike about me? I asked you to be 100% honest.
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you have a favorite? Is it ok if your partner does?
That one or two things that made you go hmmmm, OMG or wow!
19~ Who/when was your first “heartbreak”?
7- What are your thoughts on religion? Is there an afterlife?
9~ How many times over your lifetime do you think you have had sex so far?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
26~ What side of the bed do you sleep on?
89~ Do you like taking showers together?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
52~ What are your hobbies?
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?
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…
How well do you know me? And some of your thoughts about me
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Escort/Client Job Applicant/Hiring Manager
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
32- What's your greatest talent? Can I see it right now?
If NO, would you ever have one? Would it be with 2 men or 2 women?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If yes, what?
* Give a rating for each one (0-100)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
18~ Who/when was your first “crush”?
Would you do it again, and would you rather 2 females or 2 males?
Model/Photographer Police/Criminal
Any that are a turn off?
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,
38~ Share your most embarrassing sexual memory?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
21- What's your favorite way to spend a weekend or time off?
What have you learned about me that was new and/or surprising?
The Ice Breaker Questions
84~ How do you feel about reading/listening to adult stories?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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…
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What would you say to prove to yourself that it was really you?
Can you Deep Throat? Do you like the taste of yourself?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Any that are a turn off?
Master/Slave Boss/Maid
Would you read them together?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
76~ Have you had a threesome? Care to Share?
39~ What are your love languages?
28~ What are some things that turn on? What is your biggest turn on?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
17- Have you ever done drugs? Which ones? How often?
10~ How many dates are necessary before you to have sex with someone?
14- What is an embarrassing moment in your life? How about your most embarrassing?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
If you say it, I will stop, and we can talk about it when you are ready.
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
42~ What’s your biggest regret in life?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
27- What was/ is nickname? Does it have a meaning behind it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Repairman/Lonely Wife Virgin/Experienced
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
13- What is the craziest/scariest thing you've ever done?
Teacher/Student Stranger/One Night Stand
4- For a pet, Cat, dog or other?
92~ Have you ever had or have an STD? How many? What was it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
44~ Care to share something about yourself that no one else knows about you?
10- What is your favorite family tradition? What’s your least favorite?
23- What is your dream job? What was it as a child?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
7- What if a person smells a certain way? 8- How about smoking?
1- What was your first impression of me? Has it changed?
82~ Do you have any fantasies involving Role-Playing?
67~ Do you like it when your partner moans and/or is vocal during sex?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
Does the thought excite you? Care to share?
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)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
48~ Have you ever paid or been paid for sex?
61~ How willing would you be to try new sexual positions?
83~ How do you feel about Porn?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5- Have you ever been hypnotized? Would you allow yourself to be?
19- What’s your favorite fairytale? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How many partners have you had oral sex with? Who? Care to Share?
13- How about having a certain hair cut/style?
15- What bad habit do you wish you could quit? Do you have any addictions?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Get this wrong and this could mean the end… :-) some funny, some not…
Over time has your thoughts on sex changed?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
34~ Do you like the lights on or off during sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
I would allow you to do it… What would you do to me?
11- What's your favorite restaurant? What’s your least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What was the longest? What was the shortest?
3- What Superhero or Superpower would you want to be/have?
62~ Have you used adult toys?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
18- How often do you drink alcohol? What is your favorite drink?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
50~ How many children do you have? What are their ages?
49~ How many times have you been married? Why did they end?
29- How superstitious are you?
Do you think this brought you closer together?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
21~ What was the best date you ever went on? What has been the worst?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
19- Do/have you smoked? What do you prefer? How often?
33- If you could visit any time period, when would you pick? Please explain why?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
17- What’s your favorite holiday? What’s your least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
What have you learned about yourself that you did not before this?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
65~ Describe the best orgasm you’ve ever had? 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?
30~ What's something unexpected that turns you on?
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)
9- What’s your favorite season and why? What’s your least favorite?
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?