What is the most interesting question you can ask to get to know someone?
13.06.2025 01:13
Escort/Client Job Applicant/Hiring Manager
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
*** Questions about Relationships/Past ***
Can you share a story of someone who had a lucky experience while hitchhiking?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Would you mind if your partner watched it? How about together vs alone?
14- What's your favorite dessert? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
11- List at least 5 things on your bucket list. Have you done any of them already?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What is your favorite toy? Ever wanted to try a specific toy?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Why does my crush make me jealous about having a girlfriend?
11~ Have you ever been caught by your parents or children or others while having sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Repairman/Lonely Wife Virgin/Experienced
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How many partners have you had oral sex with? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
Family Relation Age Play
How old are you? Male or Female?
67~ Do you like it when your partner moans and/or is vocal during sex?
37- Do you like your name? If you could change it, what would you change it too?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Has anyone been spanked by their parents after becoming an adult?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
33- If you could visit any time period, when would you pick? Please explain why?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How can someone get patrons on Patreon if they are a beginner artist?
23- What is your dream job? What was it as a child?
Over time has your thoughts on sex changed?
51~ What tends to bring a smile to your face?
What is the problem between Turkey and Greece?
Do you have a favorite? Is it ok if your partner does?
4- For a pet, Cat, dog or other?
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
8- What are your thoughts on politics?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
10- What is your favorite family tradition? What’s your least favorite?
Prisoner/Prison Guard Landlord/Tenant
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
34~ Do you like the lights on or off during sex?
Do you like it when they show and tell you what they want?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
7-What do I do in bed that drives you wild? How about, what turns you off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
27- What was/ is nickname? Does it have a meaning behind it?
36~ What is your favorite time of day to have sex/make love?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
92~ Have you ever had or have an STD? How many? What was it?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What do you dislike about me? I asked you to be 100% honest.
* Give a rating for each one (0-100)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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,
9~ How many times over your lifetime do you think you have had sex so far?
5- Have you ever been hypnotized? Would you allow yourself to be?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** Questions About Me ***
If yes, what?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
81~ Do you have any kinks and/or fetishes?
If NO, would you ever have one? Would it be with 2 men or 2 women?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What is your view on sex? Meaning, When/Where/ How often/
83~ How do you feel about Porn?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
*** Deal Breaker Questions ***
44~ Care to share something about yourself that no one else knows about you?
22- Do you have any birth marks? How about scars? Care to share how you got them?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Please share Did you stop?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
13- How about having a certain hair cut/style?
34- Ever been to a concert? What was your favorite? Who would you like to see?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
18- How often do you drink alcohol? What is your favorite drink?
47~ What would be your dream job and why?
Would you ever want to be woken up with oral and/or intercourse?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
9- If you could have three wishes, what would they be? Why?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
22- What is your favorite childhood memory? What is your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
1- What’s your favorite animal? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
Will you kiss after your partner has gone down on you? Swallow or spit semen?
20- What’s your favorite candy? What’s your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
If you win, what will you make them do?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
Do you like the “69” position? Do you prefer to be on top or bottom?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What was the longest? What was the shortest?
29- How superstitious are you?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
25~ How do you feel about PDA? (Public Display of Affection)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What would you say to prove to yourself that it was really you?
17- What’s your favorite holiday? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
28~ What are some things that turn on? What is your biggest turn on?
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…
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?
89~ Do you like taking showers together?
You know that I will be 100% truthful, so ask.
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched 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?
19~ Who/when was your first “heartbreak”?
21~ What was the best date you ever went on? What has been the worst?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
84~ How do you feel about reading/listening to adult stories?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
18~ Who/when was your first “crush”?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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)
If you say it, I will stop, and we can talk about it when you are ready.
38~ Share your most embarrassing sexual memory?
31- If given a chance to be immortal, would you take it? Why?
53~ How much can you tell me about the one thing you are most passionate about?
Do you think this brought you closer together?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
61~ How willing would you be to try new sexual positions?
Have you ever? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
What have you learned about me that was new and/or surprising?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
30~ What's something unexpected that turns you on?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Get this wrong and this could mean the end… :-) some funny, some not…
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
The Ice Breaker Questions
19- What’s your favorite fairytale? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
13- What’s your favorite drink? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
*** What’s Your Favorite…? ***
12- What’s your favorite food? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
What is your favorite position? Why?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Any that are a turn off?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Would you do it again, and would you rather 2 females or 2 males?
Would you read them together?
Would /have you ever given your partner a lap dance and Striptease?
9- What’s your favorite season and why? What’s your least favorite?
How many times do you think you have “made love”?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
39~ What are your love languages?
10~ How many dates are necessary before you to have sex with someone?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Can you Deep Throat? Do you like the taste of yourself?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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?
Any that are a turn off?
1- What was your first impression of me? Has it changed?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
I would allow you to do it… What would you do to me?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Master/Slave Boss/Maid
Nothing too Serious
How about if they talk dirty and/or call you names?
52~ What are your hobbies?
21- What's your favorite way to spend a weekend or time off?
19- Do/have you smoked? What do you prefer? How often?
15- What bad habit do you wish you could quit? Do you have any addictions?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
15~ Have you ever been “in love”? Who? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
92~ Everyone needs a “safe” word. What is yours?
3- What’s your favorite smell? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
36- Do you play video games? What is your favorite? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
That one or two things that made you go hmmmm, OMG or wow!
What have you learned about yourself that you did not before this?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
3- What Superhero or Superpower would you want to be/have?
26~ What side of the bed do you sleep on?
48~ Do you have any siblings? Are you close to your family?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
2- What’s your favorite color? Do you a least favorite?
28- What are some things that people do that irritate you?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
6- Do you have dreams? Can you remember them? What do you usually dream about?
How well do you know me? And some of your thoughts about me
51~ Are you willing to play adult games with your partner?
33- Beach or Mountains? Or is there another place to like better?
13~ Is there a difference between, making love, having sex, and fucking?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Doctor/Nurse Stripper/Client
76~ Have you had a threesome? Care to Share?
13- What is the craziest/scariest thing you've ever done?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
(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…)
82~ Do you have any fantasies involving Role-Playing?
14- What is an embarrassing moment in your life? How about your most embarrassing?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
*** Random Questions ***
7- What if a person smells a certain way? 8- How about smoking?
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…
29~ What are some things that turn you off? What is your biggest turn off?
70~ Would/do you have/like anal sex?
Does the thought excite you? Care to share?
71~ Would you give your partner a hand or foot job? Would you receive one?
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)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
7- What are your thoughts on religion? Is there an afterlife?
12- What is the weirdest thing you've ever eaten?
If YES, was it with 2 men or 2 women? Did you enjoy it?
42~ What’s your biggest regret in life?
49~ How many times have you been married? Why did they end?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
50~ How many children do you have? What are their ages?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
10- List 5 of your top pet peeves.
62~ Have you used adult toys?
3- Should Pluto still be considered a planet? 4- How about smoking?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
17- Have you ever done drugs? Which ones? How often?
11- What's your favorite restaurant? What’s your least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Do you watch it? What is your favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Nurse/Patient Celebrity/Fan
48~ Have you ever paid or been paid for sex?
32- What's your greatest talent? Can I see it right now?
Model/Photographer Police/Criminal