What is the most interesting question you can ask to get to know someone?
Last Updated: 29.06.2025 20:36
61~ How willing would you be to try new sexual positions?
*** Questions about Relationships/Past ***
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Why do North Indians, living in Bangalore, not bother to learn Kannada?
10- What is your favorite family tradition? What’s your least favorite?
What do you dislike about me? I asked you to be 100% honest.
*** Questions About Me ***
Kroger Faces Backlash as Juneteenth Cakes Go Viral - Newser
9~ How many times over your lifetime do you think you have had sex so far?
65~ Describe the best orgasm you’ve ever had? Care to share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
My son flunked his road test because he was driving a Tesla, dad says - NJ.com
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
What would you say to prove to yourself that it was really you?
Common blood pressure drug slows aging and boosts lifespan, even in older animals - Earth.com
7- What if a person smells a certain way? 8- How about smoking?
Prisoner/Prison Guard Landlord/Tenant
Nothing too Serious
26~ What side of the bed do you sleep on?
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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
China extracts critical mineral rubidium from brine for first time - South China Morning Post
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
'Strawberry Moon' 2025: June's full moon is about to break an annual record - Live Science
21- What's your favorite way to spend a weekend or time off?
28~ What are some things that turn on? What is your biggest turn on?
31- If given a chance to be immortal, would you take it? Why?
People are just learning of the most deadly disease that often goes undiagnosed by doctors - UNILAD
10~ How many dates are necessary before you to have sex with someone?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Repairman/Lonely Wife Virgin/Experienced
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
How can I plan a zero-waste vacation without compromising on comfort?
92~ Have you ever had or have an STD? How many? What was it?
15~ Have you ever been “in love”? Who? Care to Share?
39~ What are your love languages?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Teacher/Student Stranger/One Night Stand
49~ How many times have you been married? Why did they end?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
13- What’s your favorite drink? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
27- What was/ is nickname? Does it have a meaning behind it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
51~ What tends to bring a smile to your face?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Would you read them together?
Family Relation Age Play
If you win, what will you make them do?
76~ Have you had a threesome? Care to Share?
Do you watch it? What is your favorite?
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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
23- What is your dream job? What was it as a child?
51~ Are you willing to play adult games with your partner?
52~ What are your hobbies?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What is your favorite position? Why?
Would you ever want to be woken up with oral and/or intercourse?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
5~ When you first started having sex, was it what you thought it would be?
19~ Who/when was your first “heartbreak”?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What is your view on sex? Meaning, When/Where/ How often/
30~ What's something unexpected that turns you on?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Over time has your thoughts on sex changed?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What have you learned about yourself that you did not before this?
9- If you could have three wishes, what would they be? Why?
Doctor/Nurse Stripper/Client
81~ Do you have any kinks and/or fetishes?
52~ Are you willing to make “those types” of bets with your partner?
What have you learned about me that was new and/or surprising?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
34- Ever been to a concert? What was your favorite? Who would you like to see?
How many times do you think you have “made love”?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
11- List at least 5 things on your bucket list. Have you done any of them already?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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…
36- Do you play video games? What is your favorite? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
25~ How do you feel about PDA? (Public Display of Affection)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
13- What is the craziest/scariest thing you've ever done?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
10- List 5 of your top pet peeves.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
12- What’s your favorite food? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
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?
47~ What would be your dream job and why?
Have you ever? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Escort/Client Job Applicant/Hiring Manager
Do you think this brought you closer together?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
9- Is there something you’ve always wanted to ask me but you’re afraid?
3- What Superhero or Superpower would you want to be/have?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If yes, what?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
7-What do I do in bed that drives you wild? How about, what turns you off?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
How well do you know me? And some of your thoughts about me
28- What are some things that people do that irritate you?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
(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…)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
17- Have you ever done drugs? Which ones? How often?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Do you like it when they show and tell you what they want?
Get this wrong and this could mean the end… :-) some funny, some not…
60~ How important is oral sex? Do you like receiving? Do you like giving?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
7- What are your thoughts on religion? Is there an afterlife?
Can you Deep Throat? Do you like the taste of yourself?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
84~ How do you feel about reading/listening to adult stories?
What is your favorite toy? Ever wanted to try a specific toy?
3- What’s your favorite smell? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Master/Slave Boss/Maid
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
* Give a rating for each one (0-100)
12- What is the weirdest thing you've ever eaten?
45~ How do you feel about me blindfolding you? How about blindfolding me?
*** Deal Breaker Questions ***
1- What was your first impression of me? Has it changed?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
How many partners have you had oral sex with? Who? Care to Share?
34~ Do you like the lights on or off during sex?
How about if they talk dirty and/or call you names?
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?
How old are you? Male or Female?
70~ Would/do you have/like anal sex?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
Nurse/Patient Celebrity/Fan
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
3- Should Pluto still be considered a planet? 4- How about smoking?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
18~ Who/when was your first “crush”?
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?
33- Beach or Mountains? Or is there another place to like better?
9- What’s your favorite season and why? What’s your least favorite?
Does the thought excite you? Care to share?
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?
1- What’s your favorite animal? Do you a least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
33- If you could visit any time period, when would you pick? Please explain why?
89~ Do you like taking showers together?
I would allow you to do it… What would you do to me?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
83~ How do you feel about Porn?
11- What's your favorite restaurant? What’s your least favorite?
2- What’s your favorite color? 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?
13- How about having a certain hair cut/style?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
19- What’s your favorite fairytale? What’s your least favorite?
50~ How many children do you have? What are their ages?
21~ What was the best date you ever went on? What has been the worst?
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?
8- What are your thoughts on politics?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Please share Did you stop?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
48~ Do you have any siblings? Are you close to your family?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
If you say it, I will stop, and we can talk about it when you are ready.
11- How about if they like a certain sports team? 12-How about drinking too much?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
44~ Care to share something about yourself that no one else knows about you?
What was the longest? What was the shortest?
Do you like the “69” position? Do you prefer to be on top or bottom?
29~ What are some things that turn you off? What is your biggest turn off?
15- What's your favorite saying? What word or phrase is your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
6- Do you have dreams? Can you remember them? What do you usually dream about?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
5- Have you ever been hypnotized? Would you allow yourself to be?
29- How superstitious are you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
53~ How much can you tell me about the one thing you are most passionate about?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
3- What was the most surprising thing you’ve learned about me throughout our relationship?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
*** What’s Your Favorite…? ***
Would /have you ever given your partner a lap dance and Striptease?
Any that are a turn off?
Model/Photographer Police/Criminal
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
You know that I will be 100% truthful, so ask.
13~ Is there a difference between, making love, having sex, and fucking?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
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,
42~ What’s your biggest regret in life?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
15- What bad habit do you wish you could quit? Do you have any addictions?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
*** Random Questions ***
38~ Share your most embarrassing sexual memory?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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 have a favorite? Is it ok if your partner does?
22- What is your favorite childhood memory? What is your least favorite?
92~ Everyone needs a “safe” word. What is yours?
36~ What is your favorite time of day to have sex/make love?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
18- How often do you drink alcohol? What is your favorite drink?
4- For a pet, Cat, dog or other?
1~ How old were you when you had your first kiss? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
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?
The Ice Breaker Questions
That one or two things that made you go hmmmm, OMG or wow!
18- What’s your favorite way to relax after a long day? What’s your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
32- What's your greatest talent? Can I see it right now?
11~ Have you ever been caught by your parents or children or others while having sex?
62~ Have you used adult toys?
40~ What’s the weirdest place you’ve ever had sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
14- What's your favorite dessert? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
71~ Would you give your partner a hand or foot job? Would you receive one?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?