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