What is the most interesting question you can ask to get to know someone?
08.06.2025 13:23
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
70~ Would/do you have/like anal sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
How do people develop stage 4 cancer without noticing until it’s too late?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What have you learned about me that was new and/or surprising?
48~ Do you have any siblings? Are you close to your family?
After 600 Years, Astronomers Finally Solve the Mystery of the Missing ‘Guest Star’ - Gizmodo
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
76~ Have you had a threesome? Care to Share?
Solar Storms Are Pushing Elon Musk’s Satellites Back to Earth - Gizmodo
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Why do I sometimes hear full conversations when I am alone?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
17- Have you ever done drugs? Which ones? How often?
13- What is the craziest/scariest thing you've ever done?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Mets’ need their all-time lost opportunity to be a Dodgers aberration - New York Post
What is your view on sex? Meaning, When/Where/ How often/
52~ Are you willing to make “those types” of bets with your partner?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Stopping alcoholism gets smarter with smartwatches - The Brighter Side of News
71~ Would you give your partner a hand or foot job? Would you receive one?
How about if they talk dirty and/or call you names?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What does it feel like wearing tights?
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?
28- What are some things that people do that irritate you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
I am glad you enjoyed my pictures. Do you have any photos to share?
Would /have you ever given your partner a lap dance and Striptease?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Would you allow me to clean every part of your body with my soapy hands and fingers?
James Webb Space Telescope unveils fiery origins of a distant, hellish exoplanet - Space
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Does the thought excite you? Care to share?
*** Questions about Relationships/Past ***
Why cant I motivate myself to go to school (grade 10)?
What would you say to prove to yourself that it was really you?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
I would allow you to do it… What would you do to me?
Why do you think Democrat favorability ratings are so low?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
33- Beach or Mountains? Or is there another place to like better?
Earth’s oldest living creature unearthed—dating back 700 million years - The Brighter Side of News
Get this wrong and this could mean the end… :-) some funny, some not…
Doctor/Nurse Stripper/Client
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** What’s Your Favorite…? ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
32- What's your greatest talent? Can I see it right now?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Any that are a turn off?
12- What is the weirdest thing you've ever eaten?
Would you do it again, and would you rather 2 females or 2 males?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If YES, was it with 2 men or 2 women? Did you enjoy it?
39~ What are your love languages?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13~ Is there a difference between, making love, having sex, and fucking?
29~ What are some things that turn you off? What is your biggest turn off?
How old are you? Male or Female?
51~ What tends to bring a smile to your face?
Do you like the “69” position? Do you prefer to be on top or bottom?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
62~ Have you used adult toys?
1~ How old were you when you had your first kiss? Who? Care to Share?
12- What’s your favorite food? 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?
36~ What is your favorite time of day to have sex/make love?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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?
Would you ever want to be woken up with oral and/or intercourse?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
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”?
What do you dislike about me? I asked you to be 100% honest.
How many partners have you had oral sex with? Who? Care to Share?
51~ Are you willing to play adult games with your partner?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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…
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
10- What is your favorite family tradition? What’s your least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
If NO, would you ever have one? Would it be with 2 men or 2 women?
20- What’s your favorite candy? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
42~ What’s your biggest regret in life?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
19- Do/have you smoked? What do you prefer? How often?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
19- What’s your favorite fairytale? What’s your least favorite?
26~ What side of the bed do you sleep on?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
If you say it, I will stop, and we can talk about it when you are ready.
13- How about having a certain hair cut/style?
What was the longest? What was the shortest?
30~ What's something unexpected that turns you on?
Over time has your thoughts on sex changed?
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 favorite toy? Ever wanted to try a specific toy?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
10- List 5 of your top pet peeves.
Have you ever? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
47~ What would be your dream job and why?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
Any that are a turn off?
31- If given a chance to be immortal, would you take it? Why?
8- What are your thoughts on politics?
2- What’s your favorite color? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
* Give a rating for each one (0-100)
50~ How many children do you have? What are their ages?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
18- How often do you drink alcohol? What is your favorite drink?
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
19~ Who/when was your first “heartbreak”?
7- What are your thoughts on religion? Is there an afterlife?
1- What was your first impression of me? Has it changed?
28~ What are some things that turn on? What is your biggest turn on?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Teacher/Student Stranger/One Night Stand
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
1- What’s your favorite animal? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
92~ Have you ever had or have an STD? How many? What was it?
14- What's your favorite dessert? Do you a least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
(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…)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
52~ What are your hobbies?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
40~ What’s the weirdest place you’ve ever had sex?
6- Do you have dreams? Can you remember them? What do you usually dream about?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
15~ Have you ever been “in love”? Who? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
Nurse/Patient Celebrity/Fan
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
10~ How many dates are necessary before you to have sex with someone?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
89~ Do you like taking showers together?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you think this brought you closer together?
61~ How willing would you be to try new sexual positions?
81~ Do you have any kinks and/or fetishes?
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)
25~ How do you feel about PDA? (Public Display of Affection)
45~ How do you feel about me blindfolding you? How about blindfolding me?
17- What’s your favorite holiday? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Would you mind if your partner watched it? How about together vs alone?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
82~ Do you have any fantasies involving Role-Playing?
7-What do I do in bed that drives you wild? How about, what turns you off?
What is your favorite position? Why?
23- What is your dream job? What was it as a child?
Can you Deep Throat? Do you like the taste of yourself?
65~ Describe the best orgasm you’ve ever had? Care to share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
You know that I will be 100% truthful, so ask.
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,
*** Random Questions ***
Do you have a favorite? Is it ok if your partner does?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
67~ Do you like it when your partner moans and/or is vocal during sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
7- What if a person smells a certain way? 8- How about smoking?
22- What is your favorite childhood memory? What is your least favorite?
Repairman/Lonely Wife Virgin/Experienced
Nothing too Serious
If you win, what will you make them do?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Master/Slave Boss/Maid
38~ Share your most embarrassing sexual memory?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9- If you could have three wishes, what would they be? Why?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
29- How superstitious are you?
92~ Everyone needs a “safe” word. What is yours?
How well do you know me? And some of your thoughts about me
48~ Have you ever paid or been paid for sex?
21~ What was the best date you ever went on? What has been the worst?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
The Ice Breaker Questions
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would you read them together?
*** Deal Breaker Questions ***
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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…
Escort/Client Job Applicant/Hiring Manager
What have you learned about yourself that you did not before this?
3- What’s your favorite smell? Do you a least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Family Relation Age Play
Do you watch it? What is your favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
15- What's your favorite saying? What word or phrase is your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
4- For a pet, Cat, dog or other?
3- What Superhero or Superpower would you want to be/have?
83~ How do you feel about Porn?
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
8- What's your favorite flavor of ice cream? Do you a least favorite?
If yes, what?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Model/Photographer Police/Criminal
36- Do you play video games? What is your favorite? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** Questions About Me ***
How many times do you think you have “made love”?
Please share Did you stop?
Will you cheat again? How can, you be sure? Define what cheating is to you.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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?
21- What's your favorite way to spend a weekend or time off?
11~ Have you ever been caught by your parents or children or others while having sex?
That one or two things that made you go hmmmm, OMG or wow!
3- Should Pluto still be considered a planet? 4- How about smoking?
5~ When you first started having sex, was it what you thought it would be?
49~ How many times have you been married? Why did they end?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
9- What’s your favorite season and why? What’s your least favorite?
34~ Do you like the lights on or off during sex?
Prisoner/Prison Guard Landlord/Tenant
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Do you like it when they show and tell you what they want?
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?
11- What's your favorite restaurant? What’s your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
3- What was the most surprising thing you’ve learned about me throughout our relationship?