What is the most interesting question you can ask to get to know someone?
Last Updated: 27.06.2025 17:23
14- What is an embarrassing moment in your life? How about your most embarrassing?
What is your view on sex? Meaning, When/Where/ How often/
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If you win, what will you make them do?
39~ What are your love languages?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Doloremque harum est natus ipsum quasi at atque quam.
21~ What was the best date you ever went on? What has been the worst?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
65~ Describe the best orgasm you’ve ever had? Care to share?
50~ How many children do you have? What are their ages?
33- If you could visit any time period, when would you pick? Please explain why?
83~ How do you feel about Porn?
ChatGPT wasn’t built for this, but it’s now the center of my daily routine - Android Authority
Would you mind if your partner watched it? How about together vs alone?
31- If given a chance to be immortal, would you take it? Why?
1~ How old were you when you had your first kiss? Who? Care to Share?
Study shows that early humans climbed trees and worked with stone - Earth.com
Have you ever? 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…)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What are the top 10 AI business ideas to start today?
Do you watch it? What is your favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
19~ Who/when was your first “heartbreak”?
Google quietly released an app that lets you download and run AI models locally - TechCrunch
Over time has your thoughts on sex changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
The #1 Underrated Vegetable with More Vitamin C Than an Orange, According to Dietitians - EatingWell
11- What's your favorite restaurant? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Royals share new photos of Prince William with children - BBC
11- How about if they like a certain sports team? 12-How about drinking too much?
2- What’s your favorite color? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
Helen Hunt on why she's rejecting Hollywood beauty standards - USA Today
3- What Superhero or Superpower would you want to be/have?
9- What’s your favorite season and why? What’s your least favorite?
What have you learned about me that was new and/or surprising?
Would /have you ever given your partner a lap dance and Striptease?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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?
NASA’s Webb Rounds Out Picture of Sombrero Galaxy’s Disk - NASA Science (.gov)
19- What’s your favorite fairytale? What’s your least favorite?
8- What are your thoughts on politics?
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)
9- Is there something you’ve always wanted to ask me but you’re afraid?
51~ What tends to bring a smile to your face?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
29- How superstitious are you?
15- What's your favorite saying? What word or phrase is your least favorite?
Escort/Client Job Applicant/Hiring Manager
36~ What is your favorite time of day to have sex/make love?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
I would allow you to do it… What would you do to me?
61~ How willing would you be to try new sexual positions?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Nurse/Patient Celebrity/Fan
9- If you could have three wishes, what would they be? Why?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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?
How many times do you think you have “made love”?
84~ How do you feel about reading/listening to adult stories?
26~ What side of the bed do you sleep on?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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…
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,
Nothing too Serious
Would you read them together?
67~ Do you like it when your partner moans and/or is vocal during sex?
How old are you? Male or Female?
Would you allow me to clean every part of your body with my soapy hands and fingers?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Please share Did you stop?
11- List at least 5 things on your bucket list. Have you done any of them already?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What was the longest? What was the shortest?
22- What is your favorite childhood memory? What is your least favorite?
34~ Do you like the lights on or off during sex?
7- What if a person smells a certain way? 8- How about smoking?
32- What's your greatest talent? Can I see it right now?
42~ What’s your biggest regret in life?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
52~ Are you willing to make “those types” of bets with your partner?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
44~ Care to share something about yourself that no one else knows about you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
18~ Who/when was your first “crush”?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Family Relation Age Play
Do you shave/trim your pubic hair? For you guys do you shave your balls?
7- What are your thoughts on religion? Is there an afterlife?
Would you do it again, and would you rather 2 females or 2 males?
36- Do you play video games? What is your favorite? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
Any that are a turn off?
* Give a rating for each one (0-100)
10- List 5 of your top pet peeves.
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
12- What is the weirdest thing you've ever eaten?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
7-What do I do in bed that drives you wild? How about, what turns you off?
48~ Do you have any siblings? Are you close to your family?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What have you learned about yourself that you did not before this?
28~ What are some things that turn on? What is your biggest turn on?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Repairman/Lonely Wife Virgin/Experienced
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
21- What's your favorite way to spend a weekend or time off?
82~ Do you have any fantasies involving Role-Playing?
41~ Are there moments in your past that you would want to change? Please share 3 of 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?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
92~ Have you ever had or have an STD? How many? What was it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
92~ Everyone needs a “safe” word. What is yours?
If NO, would you ever have one? Would it be with 2 men or 2 women?
11~ Have you ever been caught by your parents or children or others while having sex?
How many partners have you had oral sex with? Who? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
23- What is your dream job? What was it as a child?
5- Have you ever been hypnotized? Would you allow yourself to be?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
3- What’s your favorite smell? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
27- What was/ is nickname? Does it have a meaning behind it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Any that are a turn off?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
48~ Have you ever paid or been paid for sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
13- What is the craziest/scariest thing you've ever done?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
10~ How many dates are necessary before you to have sex with someone?
25~ How do you feel about PDA? (Public Display of Affection)
Can you Deep Throat? Do you like the taste of yourself?
What would you say to prove to yourself that it was really you?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
5~ When you first started having sex, was it what you thought it would be?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
*** Questions About Me ***
Do you like it when they show and tell you what they want?
What is your favorite toy? Ever wanted to try a specific toy?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
28- What are some things that people do that irritate you?
If you say it, I will stop, and we can talk about it when you are ready.
Do you have a favorite? Is it ok if your partner does?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
18- How often do you drink alcohol? What is your favorite drink?
What is your favorite position? Why?
12- What’s your favorite food? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
40~ What’s the weirdest place you’ve ever had sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
1- What’s your favorite animal? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
19- Do/have you smoked? What do you prefer? How often?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
8- What's your favorite flavor of ice cream? Do you a least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
20- What’s your favorite candy? What’s your least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Doctor/Nurse Stripper/Client
70~ Would/do you have/like anal sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If YES, was it with 2 men or 2 women? Did you enjoy it?
47~ What would be your dream job and why?
4- For a pet, Cat, dog or other?
You know that I will be 100% truthful, so ask.
53~ How much can you tell me about the one thing you are most passionate about?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
*** What’s Your Favorite…? ***
49~ How many times have you been married? Why did they end?
Model/Photographer Police/Criminal
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…
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
71~ Would you give your partner a hand or foot job? Would you receive one?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
1- What was your first impression of me? Has it changed?
81~ Do you have any kinks and/or fetishes?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Does the thought excite you? Care to share?
How about if they talk dirty and/or call you names?
37- Do you like your name? If you could change it, what would you change it too?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Get this wrong and this could mean the end… :-) some funny, some not…
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
30~ What's something unexpected that turns you on?
Prisoner/Prison Guard Landlord/Tenant
13- How about having a certain hair cut/style?
13- What’s your favorite drink? What’s your least favorite?
If yes, what?
9~ How many times over your lifetime do you think you have had sex so far?
13~ Is there a difference between, making love, having sex, and fucking?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What do you dislike about me? I asked you to be 100% honest.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
That one or two things that made you go hmmmm, OMG or wow!
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
22- Do you have any birth marks? How about scars? Care to share how you got them?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
The Ice Breaker Questions
51~ Are you willing to play adult games with your partner?
17- Have you ever done drugs? Which ones? How often?
Would you ever want to be woken up with oral and/or intercourse?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
52~ What are your hobbies?
Master/Slave Boss/Maid
Teacher/Student Stranger/One Night Stand
Do you think this brought you closer together?
*** Questions about Relationships/Past ***
80~ Share your top three fantasies/desires. (Be detailed) 😊
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
38~ Share your most embarrassing sexual memory?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
15~ Have you ever been “in love”? Who? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
15- What bad habit do you wish you could quit? Do you have any addictions?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Do you like the “69” position? Do you prefer to be on top or bottom?
How well do you know me? And some of your thoughts about me
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
*** Deal Breaker Questions ***
*** Random Questions ***
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
10- What is your favorite family tradition? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?