What is the most interesting question you can ask to get to know someone?
Last Updated: 01.07.2025 00:06
Master/Slave Boss/Maid
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What are your main K-pop groups? (Or groups you listen to)?
What would you say to prove to yourself that it was really you?
60~ How important is oral sex? Do you like receiving? Do you like giving?
If you win, what will you make them do?
Why in my 60s do I have a strong desire to suck cock and swallow?
Can you Deep Throat? Do you like the taste of yourself?
You know that I will be 100% truthful, so ask.
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
37- Do you like your name? If you could change it, what would you change it too?
Do you have a favorite? Is it ok if your partner does?
1- What was your first impression of me? Has it changed?
What is your favorite toy? Ever wanted to try a specific toy?
Would you mind if your partner watched it? How about together vs alone?
Escort/Client Job Applicant/Hiring Manager
Is a man over 50 not married no kids a red flag?
29~ What are some things that turn you off? What is your biggest turn off?
What is your favorite position? Why?
Do you think this brought you closer together?
Man thought he was 'tired from work' before brain tumour diagnosis - BBC
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
33- Beach or Mountains? Or is there another place to like better?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Any that are a turn off?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Why do people say "tall, dark, and handsome" when they actually mean "tall, white, and handsome"?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Why does my mom never wear underwear?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Please share Did you stop?
1- What’s your favorite animal? Do you a least favorite?
WWE monitoring US-Iran situation with two Saudi Arabia shows set for next weekend - New York Post
Have you ever? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
9- If you could have three wishes, what would they be? Why?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
23- What is your dream job? What was it as a child?
How do I get a white man for a serious relationship?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
14- What's your favorite dessert? Do you a least favorite?
44~ Care to share something about yourself that no one else knows about you?
Is Taylor Swift aware of the fact that she’s naturally seductive?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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…
19~ Who/when was your first “heartbreak”?
62~ Have you used adult toys?
13- What’s your favorite drink? What’s your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
11- How about if they like a certain sports team? 12-How about drinking too much?
*** What’s Your Favorite…? ***
What was the longest? What was the shortest?
Does the thought excite you? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
33- If you could visit any time period, when would you pick? Please explain why?
52~ What are your hobbies?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Doctor/Nurse Stripper/Client
Would you do it again, and would you rather 2 females or 2 males?
Get this wrong and this could mean the end… :-) some funny, some not…
7- What if a person smells a certain way? 8- How about smoking?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
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?
9- What’s your favorite season and why? What’s your least favorite?
2- What’s your favorite color? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
61~ How willing would you be to try new sexual positions?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Nurse/Patient Celebrity/Fan
47~ What would be your dream job and why?
*** Questions About Me ***
How many times do you think you have “made love”?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
How about if they talk dirty and/or call you names?
31- If given a chance to be immortal, would you take it? Why?
49~ How many times have you been married? Why did they end?
81~ Do you have any kinks and/or fetishes?
3- What Superhero or Superpower would you want to be/have?
If NO, would you ever have one? Would it be with 2 men or 2 women?
39~ What are your love languages?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
Would you read them together?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
*** Questions about Relationships/Past ***
That one or two things that made you go hmmmm, OMG or wow!
70~ Would/do you have/like anal sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What have you learned about me that was new and/or surprising?
17- What’s your favorite holiday? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
10~ How many dates are necessary before you to have sex with someone?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
13~ Is there a difference between, making love, having sex, and fucking?
40~ What’s the weirdest place you’ve ever had sex?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
9- Is there something you’ve always wanted to ask me but you’re afraid?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Family Relation Age Play
17- Have you ever done drugs? Which ones? How often?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
45~ How do you feel about me blindfolding you? How about blindfolding me?
12- What is the weirdest thing you've ever eaten?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
8- What are your thoughts on politics?
51~ What tends to bring a smile to your face?
Would you ever want to be woken up with oral and/or intercourse?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
5- Have you ever been hypnotized? Would you allow yourself to be?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Do you watch it? What is your favorite?
32- What's your greatest talent? Can I see it right now?
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
36- Do you play video games? What is your favorite? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What do you dislike about me? I asked you to be 100% honest.
Do you like the “69” position? Do you prefer to be on top or bottom?
11~ Have you ever been caught by your parents or children or others while having sex?
48~ Do you have any siblings? Are you close to your family?
8- What's your favorite flavor of ice cream? Do you a least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
*** Random Questions ***
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
If you say it, I will stop, and we can talk about it when you are ready.
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
28- What are some things that people do that irritate you?
34~ Do you like the lights on or off during sex?
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…
83~ How do you feel about Porn?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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,
I would allow you to do it… What would you do to me?
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?
52~ Are you willing to make “those types” of bets with your partner?
What is your view on sex? Meaning, When/Where/ How often/
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
How well do you know me? And some of your thoughts about me
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
29- How superstitious are you?
26~ What side of the bed do you sleep on?
19- What’s your favorite fairytale? What’s 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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
* Give a rating for each one (0-100)
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)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
28~ What are some things that turn on? What is your biggest turn on?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
42~ What’s your biggest regret in life?
10- What is your favorite family tradition? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Model/Photographer Police/Criminal
6- Do you have dreams? Can you remember them? What do you usually dream about?
76~ Have you had a threesome? Care to Share?
The Ice Breaker Questions
50~ How many children do you have? What are their ages?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
38~ Share your most embarrassing sexual memory?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
21~ What was the best date you ever went on? What has been the worst?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
13- How about having a certain hair cut/style?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Will you cheat again? How can, you be sure? Define what cheating is to you.
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
4- For a pet, Cat, dog or other?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
12- What’s your favorite food? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
30~ What's something unexpected that turns you on?
15~ Have you ever been “in love”? Who? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
92~ Have you ever had or have an STD? How many? What was it?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
65~ Describe the best orgasm you’ve ever had? Care to share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
7-What do I do in bed that drives you wild? How about, what turns you off?
How many partners have you had oral sex with? Who? Care to Share?
Any that are a turn off?
10- List 5 of your top pet peeves.
41~ Are there moments in your past that you would want to change? Please share 3 of them.
14- What is an embarrassing moment in your life? How about your most embarrassing?
*** Deal Breaker Questions ***
11- What's your favorite restaurant? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
21- What's your favorite way to spend a weekend or time off?
7- What are your thoughts on religion? Is there an afterlife?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
89~ Do you like taking showers together?
1~ How old were you when you had your first kiss? Who? Care to Share?
51~ Are you willing to play adult games with your partner?
What have you learned about yourself that you did not before this?
19- Do/have you smoked? What do you prefer? How often?
Do you like it when they show and tell you what they want?
Nothing too Serious
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
18~ Who/when was your first “crush”?
Over time has your thoughts on sex changed?
5~ When you first started having sex, was it what you thought it would be?
Prisoner/Prison Guard Landlord/Tenant
20- What’s your favorite candy? What’s your least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
53~ How much can you tell me about the one thing you are most passionate about?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
13- What is the craziest/scariest thing you've ever done?
Would /have you ever given your partner a lap dance and Striptease?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
If yes, what?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
67~ Do you like it when your partner moans and/or is vocal during sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
36~ What is your favorite time of day to have sex/make love?
22- What is your favorite childhood memory? What is your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
15- What bad habit do you wish you could quit? Do you have any addictions?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
Repairman/Lonely Wife Virgin/Experienced
(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…)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
82~ Do you have any fantasies involving Role-Playing?
84~ How do you feel about reading/listening to adult stories?
48~ Have you ever paid or been paid for sex?
How old are you? Male or Female?
3- What’s your favorite smell? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?