What is the most interesting question you can ask to get to know someone?
08.06.2025 08:46
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
29~ What are some things that turn you off? What is your biggest turn off?
Model/Photographer Police/Criminal
Did Leonardo da Vinci paint two Mona Lisas? Where are they?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
70~ Would/do you have/like anal sex?
Why in my 60s do I have a strong desire to suck cock and swallow?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
22- What is your favorite childhood memory? What is your least favorite?
61~ How willing would you be to try new sexual positions?
If NO, would you ever have one? Would it be with 2 men or 2 women?
What is your favorite toy? Ever wanted to try a specific toy?
Doctor/Nurse Stripper/Client
Are there any industries or sectors where ChatGPT is particularly well-suited for implementation?
Nurse/Patient Celebrity/Fan
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
1- What was your first impression of me? Has it changed?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you think this brought you closer together?
(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?
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?
What is your view on sex? Meaning, When/Where/ How often/
Nothing too Serious
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Deal Breaker Questions ***
*** What’s Your Favorite…? ***
What are some of your favorite hip hop lyrics?
83~ How do you feel about Porn?
12- What is the weirdest thing you've ever eaten?
67~ Do you like it when your partner moans and/or is vocal during sex?
Simone Biles spars with Riley Gaines on social media over trans athlete debate - New York Post
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Do you watch it? What is your favorite?
Raw Milk Is Trending — Here's Why Doctors Are Seriously Concerned - BuzzFeed
5- Have you ever been hypnotized? Would you allow yourself to be?
9- Is there something you’ve always wanted to ask me but you’re afraid?
6- Do you have dreams? Can you remember them? What do you usually dream about?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Repairman/Lonely Wife Virgin/Experienced
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What are your controversial and hot takes on Naruto?
13- What’s your favorite drink? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
How about if they talk dirty and/or call you names?
Why do foolish atheists think their strange delusional theories are facts?
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- How about if they like a certain sports team? 12-How about drinking too much?
18- How often do you drink alcohol? What is your favorite drink?
Why do I sweat a great deal while exercising the same on some days and not so much on others?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
51~ Are you willing to play adult games with your partner?
53~ How much can you tell me about the one thing you are most passionate about?
Would you do it again, and would you rather 2 females or 2 males?
11- What's your favorite restaurant? What’s your least favorite?
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?
The Ice Breaker Questions
80~ Share your top three fantasies/desires. (Be detailed) 😊
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
28- What are some things that people do that irritate you?
Please share Did you stop?
9- If you could have three wishes, what would they be? Why?
36~ What is your favorite time of day to have sex/make love?
3- What’s your favorite smell? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
39~ What are your love languages?
Do you like it when they show and tell you what they want?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
1~ How old were you when you had your first kiss? Who? Care to Share?
17- What’s your favorite holiday? 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?
32- What's your greatest talent? Can I see it right now?
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would you mind if your partner watched it? How about together vs alone?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
What was the longest? What was the shortest?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If yes, what?
13- What is the craziest/scariest thing you've ever done?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
18~ Who/when was your first “crush”?
33- If you could visit any time period, when would you pick? Please explain why?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
5~ When you first started having sex, was it what you thought it would be?
89~ Do you like taking showers together?
15- What bad habit do you wish you could quit? Do you have any addictions?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
19- Do/have you smoked? What do you prefer? How often?
Have you ever? Care to Share?
2- What’s your favorite color? Do you a least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
65~ Describe the best orgasm you’ve ever had? Care to share?
38~ Share your most embarrassing sexual memory?
Can you Deep Throat? Do you like the taste of yourself?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
50~ How many children do you have? What are their ages?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
13~ Is there a difference between, making love, having sex, and fucking?
Would you read them together?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
30~ What's something unexpected that turns you on?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
13- How about having a certain hair cut/style?
62~ Have you used adult toys?
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,
7- What if a person smells a certain way? 8- How about smoking?
9~ How many times over your lifetime do you think you have had sex so far?
3- What Superhero or Superpower would you want to be/have?
23- What is your dream job? What was it as a child?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
40~ What’s the weirdest place you’ve ever had sex?
92~ Have you ever had or have an STD? How many? What was it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
Would /have you ever given your partner a lap dance and Striptease?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
19~ Who/when was your first “heartbreak”?
10~ How many dates are necessary before you to have sex with someone?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
15- What's your favorite saying? What word or phrase is your least favorite?
Teacher/Student Stranger/One Night Stand
What is your favorite position? Why?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
29- How superstitious are you?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you like the “69” position? Do you prefer to be on top or bottom?
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)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
I would allow you to do it… What would you do to me?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
76~ Have you had a threesome? Care to Share?
42~ What’s your biggest regret in life?
*** Random Questions ***
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?
If you say it, I will stop, and we can talk about it when you are ready.
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Get this wrong and this could mean the end… :-) some funny, some not…
92~ Everyone needs a “safe” word. What is yours?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
8- What are your thoughts on politics?
4- For a pet, Cat, dog or other?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Would you ever want to be woken up with oral and/or intercourse?
*** Questions about Relationships/Past ***
33- Beach or Mountains? Or is there another place to like better?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
48~ Have you ever paid or been paid for sex?
52~ What are your hobbies?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
45~ How do you feel about me blindfolding you? How about blindfolding me?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What would you say to prove to yourself that it was really you?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
31- If given a chance to be immortal, would you take it? Why?
34~ Do you like the lights on or off during sex?
47~ What would be your dream job and why?
What have you learned about yourself that you did not before this?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
What have you learned about me that was new and/or surprising?
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?
84~ How do you feel about reading/listening to adult stories?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Will you cheat again? How can, you be sure? Define what cheating is to you.
7- What are your thoughts on religion? Is there an afterlife?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
10- What is your favorite family tradition? What’s your least favorite?
* Give a rating for each one (0-100)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How many times do you think you have “made love”?
*** Questions About Me ***
49~ How many times have you been married? Why did they end?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you allow me to clean every part of your body with my soapy hands and fingers?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Does the thought excite you? Care to share?
25~ How do you feel about PDA? (Public Display of Affection)
Any that are a turn off?
52~ Are you willing to make “those types” of bets with your partner?
48~ Do you have any siblings? Are you close to your family?
Do you have a favorite? Is it ok if your partner does?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
20- What’s your favorite candy? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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?
44~ Care to share something about yourself that no one else knows about you?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If you win, what will you make them do?
21- What's your favorite way to spend a weekend or time off?
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How well do you know me? And some of your thoughts about me
9- What’s your favorite season and why? What’s your least favorite?
26~ What side of the bed do you sleep on?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
15~ Have you ever been “in love”? Who? Care to Share?
You know that I will be 100% truthful, so ask.
That one or two things that made you go hmmmm, OMG or wow!
Will you kiss after your partner has gone down on you? Swallow or spit semen?
10- List 5 of your top pet peeves.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Family Relation Age Play
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Over time has your thoughts on sex changed?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
22- Do you have any birth marks? How about scars? Care to share how you got them?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
81~ Do you have any kinks and/or fetishes?
What do you dislike about me? I asked you to be 100% honest.
3- Should Pluto still be considered a planet? 4- How about smoking?
7-What do I do in bed that drives you wild? How about, what turns you off?
17- Have you ever done drugs? Which ones? How often?
37- Do you like your name? If you could change it, what would you change it too?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
27- What was/ is nickname? Does it have a meaning behind it?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Master/Slave Boss/Maid
12- What’s your favorite food? What’s your least favorite?
1- What’s your favorite animal? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
36- Do you play video games? What is your favorite? Do you a least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
46~ Have you ever used furniture, or other types of things to aid you while having 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…
Escort/Client Job Applicant/Hiring Manager
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How many partners have you had oral sex with? Who? Care to Share?
How old are you? Male or Female?
51~ What tends to bring a smile to your face?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?