What is the most interesting question you can ask to get to know someone?
09.06.2025 09:04

What is your favorite position? Why?
22- Do you have any birth marks? How about scars? Care to share how you got them?
18~ Who/when was your first “crush”?
What does it mean when a British person says "I can't be asked"?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
38~ Share your most embarrassing sexual memory?
Do you like wearing short skirts?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What would it take for you to consider yourself a "Swiftie" like Flavor Flav?
36~ What is your favorite time of day to have sex/make love?
23- What is your dream job? What was it as a child?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Screen time and physical activity habits linked to adolescent stress and depression - PsyPost
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
7- What are your thoughts on religion? Is there an afterlife?
Please share Did you stop?
Adam Sandler will cast Derrick Henry in a movie if he rushes for 2,000 yards - NBC Sports
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you have a favorite? Is it ok if your partner does?
13- What’s your favorite drink? What’s your least favorite?
How do I overcome attachment issues?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What have you learned about me that was new and/or surprising?
51~ What tends to bring a smile to your face?
Scientists Just Found the Oldest Barred Spiral Galaxy – And It’s a Monster - SciTechDaily
84~ How do you feel about reading/listening to adult stories?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
9- If you could have three wishes, what would they be? Why?
How does it feel to watch your wife get fucked hard?
If YES, was it with 2 men or 2 women? Did you enjoy it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
3- Should Pluto still be considered a planet? 4- How about smoking?
What are the strangest parts of The Bible?
Model/Photographer Police/Criminal
That one or two things that made you go hmmmm, OMG or wow!
How many partners have you had oral sex with? Who? Care to Share?
When the sun dies, could life survive on the Jupiter ocean moon Europa? - Space
48~ Have you ever paid or been paid for sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
12- What’s your favorite food? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
Master/Slave Boss/Maid
49~ If you could, would you want to be the opposite sex for a day, week, or year?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
89~ Do you like taking showers together?
2- What’s your favorite color? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
65~ Describe the best orgasm you’ve ever had? Care to share?
Can you Deep Throat? Do you like the taste of yourself?
32- What's your greatest talent? Can I see it right now?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7- What if a person smells a certain way? 8- How about smoking?
The Ice Breaker Questions
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
17- What’s your favorite holiday? What’s your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
What do you dislike about me? I asked you to be 100% honest.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
1- What’s your favorite animal? Do you a least favorite?
Nurse/Patient Celebrity/Fan
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?
50~ How many children do you have? What are their ages?
Any that are a turn off?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
21- What's your favorite way to spend a weekend or time off?
11~ Have you ever been caught by your parents or children or others while having sex?
44~ Care to share something about yourself that no one else knows about you?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
13- How about having a certain hair cut/style?
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?
How well do you know me? And some of your thoughts about me
Over time has your thoughts on sex changed?
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?
Have you ever? Care to Share?
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?
10~ How many dates are necessary before you to have sex with someone?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
5- Have you ever been hypnotized? Would you allow yourself to be?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
*** Random Questions ***
9~ How many times over your lifetime do you think you have had sex so far?
30~ What's something unexpected that turns you on?
10- What is your favorite family tradition? What’s your least favorite?
Would you read them together?
81~ Do you have any kinks and/or fetishes?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
17- Have you ever done drugs? Which ones? How often?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What is your favorite toy? Ever wanted to try a specific toy?
* Give a rating for each one (0-100)
Any that are a turn off?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
11- How about if they like a certain sports team? 12-How about drinking too much?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
39~ What are your love languages?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
51~ Are you willing to play adult games with your partner?
3- What Superhero or Superpower would you want to be/have?
45~ How do you feel about me blindfolding you? How about blindfolding me?
83~ How do you feel about Porn?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
(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…)
52~ Are you willing to make “those types” of bets with your partner?
I would allow you to do it… What would you do to me?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
*** Deal Breaker Questions ***
Do you like the “69” position? Do you prefer to be on top or bottom?
52~ What are your hobbies?
76~ Have you had a threesome? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
19~ Who/when was your first “heartbreak”?
80~ Share your top three fantasies/desires. (Be detailed) 😊
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
22- What is your favorite childhood memory? What is your least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Do you like it when they show and tell you what they want?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Would you ever want to be woken up with oral and/or intercourse?
26~ What side of the bed do you sleep on?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
19- What’s your favorite fairytale? What’s your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
7-What do I do in bed that drives you wild? How about, what turns you off?
If NO, would you ever have one? Would it be with 2 men or 2 women?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
4- For a pet, Cat, dog or other?
3- What’s your favorite smell? Do you a least favorite?
47~ What would be your dream job and why?
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?
12- What is the weirdest thing you've ever eaten?
Will you cheat again? How can, you be sure? Define what cheating is to you.
34~ Do you like the lights on or off during sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Does the thought excite you? Care to share?
How many times do you think you have “made love”?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
*** What’s Your Favorite…? ***
13- What is the craziest/scariest thing you've ever done?
You know that I will be 100% truthful, so ask.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. 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…
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
If you win, what will you make them do?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Repairman/Lonely Wife Virgin/Experienced
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
28- What are some things that people do that irritate you?
Doctor/Nurse Stripper/Client
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
92~ Have you ever had or have an STD? How many? What was it?
34- Ever been to a concert? What was your favorite? Who would you like to see?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
18- How often do you drink alcohol? What is your favorite drink?
49~ How many times have you been married? Why did they end?
How about if they talk dirty and/or call you names?
71~ Would you give your partner a hand or foot job? Would you receive one?
11- What's your favorite restaurant? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What is your view on sex? Meaning, When/Where/ How often/
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
62~ Have you used adult toys?
What would you say to prove to yourself that it was really you?
31- If given a chance to be immortal, would you take it? Why?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If you say it, I will stop, and we can talk about it when you are ready.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
33- Beach or Mountains? Or is there another place to like better?
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?
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?
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…
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
10- List 5 of your top pet peeves.
Would /have you ever given your partner a lap dance and Striptease?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
15- What's your favorite saying? What word or phrase is your least favorite?
92~ Everyone needs a “safe” word. What is yours?
9- What’s your favorite season and why? 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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
5~ When you first started having sex, was it what you thought it would be?
40~ What’s the weirdest place you’ve ever had sex?
What have you learned about yourself that you did not before this?
Would you do it again, and would you rather 2 females or 2 males?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Get this wrong and this could mean the end… :-) some funny, some not…
If yes, what?
Would you mind if your partner watched it? How about together vs alone?
14- What's your favorite dessert? Do you a least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
33- If you could visit any time period, when would you pick? Please explain why?
13~ Is there a difference between, making love, having sex, and fucking?
19- Do/have you smoked? What do you prefer? How often?
1- What was your first impression of me? Has it changed?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
8- What are your thoughts on politics?
37- Do you like your name? If you could change it, what would you change it too?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Teacher/Student Stranger/One Night Stand
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
*** Questions about Relationships/Past ***
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
11- List at least 5 things on your bucket list. Have you done any of them already?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you allow me to clean every part of your body with my soapy hands and fingers?
20- What’s your favorite candy? What’s your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How old are you? Male or Female?
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
25~ How do you feel about PDA? (Public Display of Affection)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Nothing too Serious
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)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you think this brought you closer together?
70~ Would/do you have/like anal sex?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
61~ How willing would you be to try new sexual positions?
*** Questions About Me ***
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Escort/Client Job Applicant/Hiring Manager
8- What's your favorite flavor of ice cream? Do you a least favorite?
What was the longest? What was the shortest?
29- How superstitious are you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Do you watch it? What is your favorite?
42~ What’s your biggest regret in life?
67~ Do you like it when your partner moans and/or is vocal during sex?
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
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,
48~ Do you have any siblings? Are you close to your family?