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