What is the most interesting question you can ask to get to know someone?
11.06.2025 22:05
Prisoner/Prison Guard Landlord/Tenant
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?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Lawyers could face ‘severe’ penalties for fake AI-generated citations, UK court warns - TechCrunch
15~ Have you ever been “in love”? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Teacher/Student Stranger/One Night Stand
Panama Canal boss warns MSC ports deal threatens principle of neutrality - ft.com
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
*** Random Questions ***
If you lose, are you willing to be their sex slave for a day, (anything goes)?
How do you find out who your handler is as a targeted individual?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
13~ Is there a difference between, making love, having sex, and fucking?
Would you mind if your partner watched it? How about together vs alone?
Why would a spouse cheat if the marriage is good?
51~ Are you willing to play adult games with your partner?
Have you ever? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
WWDC 2025: New Features We Could See in watchOS 26 - MacRumors
* Give a rating for each one (0-100)
How about if they talk dirty and/or call you names?
47~ What would be your dream job and why?
I want to touch my sister’s boobs. What do I say?
10~ How many dates are necessary before you to have sex with someone?
If NO, would you ever have one? Would it be with 2 men or 2 women?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
(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…)
Any that are a turn off?
Why are people becoming increasingly hostile to pro-lifers? I am pro-life.
29- How superstitious are you?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
84~ How do you feel about reading/listening to adult stories?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
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)
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
22- What is your favorite childhood memory? What is your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
70~ Would/do you have/like anal sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
2- What’s your favorite color? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
7-What do I do in bed that drives you wild? How about, what turns you off?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
18- How often do you drink alcohol? What is your favorite drink?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Can you Deep Throat? Do you like the taste of yourself?
What was the longest? What was the shortest?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
34~ Do you like the lights on or off during sex?
92~ Everyone needs a “safe” word. What is yours?
67~ Do you like it when your partner moans and/or is vocal during sex?
76~ Have you had a threesome? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Does the thought excite you? Care to share?
Escort/Client Job Applicant/Hiring Manager
21- What's your favorite way to spend a weekend or time off?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
42~ What’s your biggest regret in life?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
11- How about if they like a certain sports team? 12-How about drinking too much?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Repairman/Lonely Wife Virgin/Experienced
Any that are a turn off?
1- What’s your favorite animal? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
18~ Who/when was your first “crush”?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
62~ Have you used adult toys?
13- What is the craziest/scariest thing you've ever done?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
14- What is an embarrassing moment in your life? How about your most embarrassing?
92~ Have you ever had or have an STD? How many? What was it?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
If you win, what will you make them do?
7- What if a person smells a certain way? 8- How about smoking?
How old are you? Male or Female?
What is your view on sex? Meaning, When/Where/ How often/
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
51~ What tends to bring a smile to your face?
26~ What side of the bed do you sleep on?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
82~ Do you have any fantasies involving Role-Playing?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Do you watch it? What is your favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you like the “69” position? Do you prefer to be on top or bottom?
What is your favorite position? Why?
29~ What are some things that turn you off? What is your biggest turn off?
25~ How do you feel about PDA? (Public Display of Affection)
36~ What is your favorite time of day to have sex/make love?
39~ What are your love languages?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
3- What Superhero or Superpower would you want to be/have?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12- What’s your favorite food? What’s your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
31- If given a chance to be immortal, would you take it? Why?
Would /have you ever given your partner a lap dance and Striptease?
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?
*** Questions about Relationships/Past ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Family Relation Age Play
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
71~ Would you give your partner a hand or foot job? Would you receive one?
81~ Do you have any kinks and/or fetishes?
What have you learned about yourself that you did not before this?
9- If you could have three wishes, what would they be? Why?
*** Deal Breaker Questions ***
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- List at least 5 things on your bucket list. Have you done any of them already?
7- What are your thoughts on religion? Is there an afterlife?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
How well do you know me? And some of your thoughts about me
11~ Have you ever been caught by your parents or children or others while having sex?
20- What’s your favorite candy? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
53~ How much can you tell me about the one thing you are most passionate about?
Would you ever want to be woken up with oral and/or intercourse?
37- Do you like your name? If you could change it, what would you change it too?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
3- Should Pluto still be considered a planet? 4- How about smoking?
9- What’s your favorite season and why? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Is there a smell that most people do not like that you do? Is there a smell 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)
That one or two things that made you go hmmmm, OMG or wow!
52~ What are your hobbies?
Would you read them together?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Please share Did you stop?
4- For a pet, Cat, dog or other?
10- List 5 of your top pet peeves.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
8- What are your thoughts on politics?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
13- How about having a certain hair cut/style?
89~ Do you like taking showers 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…
How many partners have you had oral sex with? Who? Care to Share?
Master/Slave Boss/Maid
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
13- What’s your favorite drink? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?
What would you say to prove to yourself that it was really you?
28- What are some things that people do that irritate you?
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?
28~ What are some things that turn on? What is your biggest turn on?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Do you think this brought you closer together?
65~ Describe the best orgasm you’ve ever had? Care to share?
5~ When you first started having sex, was it what you thought it would be?
52~ Are you willing to make “those types” of bets with your partner?
23- What is your dream job? What was it as a child?
30~ What's something unexpected that turns you on?
15- What bad habit do you wish you could quit? Do you have any addictions?
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,
What is your favorite toy? Ever wanted to try a specific toy?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
How many times do you think you have “made love”?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
9- Is there something you’ve always wanted to ask me but you’re afraid?
33- If you could visit any time period, when would you pick? Please explain why?
44~ Care to share something about yourself that no one else knows about you?
5- Have you ever been hypnotized? Would you allow yourself to be?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
32- What's your greatest talent? Can I see it right now?
15- What's your favorite saying? What word or phrase is your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
19- Do/have you smoked? What do you prefer? How often?
40~ What’s the weirdest place you’ve ever had sex?
9~ How many times over your lifetime do you think you have had sex so far?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
I would allow you to do it… What would you do to me?
33- Beach or Mountains? Or is there another place to like better?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Nothing too Serious
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
19~ Who/when was your first “heartbreak”?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
12- What is the weirdest thing you've ever eaten?
3- What’s your favorite smell? Do you a 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?
Model/Photographer Police/Criminal
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
*** Questions About Me ***
10- What is your favorite family tradition? What’s your least favorite?
1- What was your first impression of me? Has it changed?
6- Do you have dreams? Can you remember them? What do you usually dream about?
The Ice Breaker Questions
Will you cheat again? How can, you be sure? Define what cheating is to you.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
38~ Share your most embarrassing sexual memory?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
11- What's your favorite restaurant? What’s your least favorite?
21~ What was the best date you ever went on? What has been the worst?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
61~ How willing would you be to try new sexual positions?
Do you like it when they show and tell you what they want?
What do you dislike about me? I asked you to be 100% honest.
Nurse/Patient Celebrity/Fan
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?
You know that I will be 100% truthful, so ask.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Over time has your thoughts on sex changed?
What have you learned about me that was new and/or surprising?
*** What’s Your Favorite…? ***
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
If yes, what?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Doctor/Nurse Stripper/Client
45~ How do you feel about me blindfolding you? How about blindfolding me?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you have a favorite? Is it ok if your partner does?
If you say it, I will stop, and we can talk about it when you are ready.
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
50~ How many children do you have? What are their ages?
49~ How many times have you been married? Why did they end?
17- Have you ever done drugs? Which ones? How often?
If YES, was it with 2 men or 2 women? Did you enjoy it?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?