What is the most interesting question you can ask to get to know someone?
09.06.2025 00:30
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
22- Do you have any birth marks? How about scars? Care to share how you got them?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What caused the stock market to crash?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
29~ What are some things that turn you off? What is your biggest turn off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What are the best examples of reverse psychology?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
62~ Have you used adult toys?
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?
How well do you know me? And some of your thoughts about me
9~ How many times over your lifetime do you think you have had sex so far?
Is there an MBTI personality that is more or less likely to handle stress?
4- For a pet, Cat, dog or other?
23- What is your dream job? What was it as a child?
Do you like it when they show and tell you what they want?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
89~ Do you like taking showers together?
What are some of the best photos of your favorite Korean model?
19~ Who/when was your first “heartbreak”?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
71~ Would you give your partner a hand or foot job? Would you receive one?
What are the pros and cons of arranged marriages?
49~ How many times have you been married? Why did they end?
1~ How old were you when you had your first kiss? Who? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
How to use Google's AI-powered NotebookLM — 5 tips to get started - Tom's Guide
92~ Everyone needs a “safe” word. What is yours?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
Why are Boomers so vehemently opposed to student loan forgiveness?
What was the longest? What was the shortest?
36~ What is your favorite time of day to have sex/make love?
5- Have you ever been hypnotized? Would you allow yourself to be?
Why are white women not interested in dating Asian men? Are they not attractive to you at all?
Does the thought excite you? Care to share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Family Relation Age Play
Can I see some saggy tit pics and huge areolas pics?
Do you think this brought you closer together?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
12- What is the weirdest thing you've ever eaten?
Apple Is About to Upgrade Your Current AirPods with Some Neat New Abilities - Gear Patrol
38~ Share your most embarrassing sexual memory?
Do you watch it? What is your favorite?
14- What's your favorite dessert? Do you a least favorite?
9- If you could have three wishes, what would they be? Why?
13- How about having a certain hair cut/style?
*** Deal Breaker Questions ***
*** Questions About Me ***
You know that I will be 100% truthful, so ask.
18- How often do you drink alcohol? What is your favorite drink?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
65~ Describe the best orgasm you’ve ever had? Care to share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain 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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Any that are a turn off?
If yes, what?
52~ What are your hobbies?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Prisoner/Prison Guard Landlord/Tenant
14- What is an embarrassing moment in your life? How about your most embarrassing?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
*** Questions about Relationships/Past ***
50~ How many children do you have? What are their ages?
36- Do you play video games? What is your favorite? Do you a least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
1- What was your first impression of me? Has it changed?
Would you read them together?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
Please share Did you stop?
5~ When you first started having sex, was it what you thought it would be?
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,
Have you ever? Care to Share?
Model/Photographer Police/Criminal
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
1- What’s your favorite animal? Do you a least favorite?
2- What’s your favorite color? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
12- What’s your favorite food? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
26~ What side of the bed do you sleep on?
48~ Have you ever paid or been paid for 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…
What do you dislike about me? I asked you to be 100% honest.
Over time has your thoughts on sex changed?
*** What’s Your Favorite…? ***
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
How old are you? Male or Female?
76~ Have you had a threesome? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- What’s your favorite smell? Do you a least favorite?
Any that are a turn off?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
Repairman/Lonely Wife Virgin/Experienced
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
82~ Do you have any fantasies involving Role-Playing?
Can you Deep Throat? Do you like the taste of yourself?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
13- What’s your favorite drink? What’s your least favorite?
70~ Would/do you have/like anal sex?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
How many partners have you had oral sex with? Who? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
(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…)
15- What's your favorite saying? What word or phrase is your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
How many times do you think you have “made love”?
Nothing too Serious
25~ How do you feel about PDA? (Public Display of Affection)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
7- What are your thoughts on religion? Is there an afterlife?
If you say it, I will stop, and we can talk about it when you are ready.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
18~ Who/when was your first “crush”?
7-What do I do in bed that drives you wild? How about, what turns you off?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
48~ Do you have any siblings? Are you close to your family?
I would allow you to do it… What would you do to me?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
92~ Have you ever had or have an STD? How many? What was it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
21- What's your favorite way to spend a weekend or time off?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If you win, what will you make them do?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Would you mind if your partner watched it? How about together vs alone?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
19- What’s your favorite fairytale? What’s your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
19- Do/have you smoked? What do you prefer? How often?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If NO, would you ever have one? Would it be with 2 men or 2 women?
15~ Have you ever been “in love”? Who? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
33- Beach or Mountains? Or is there another place to like better?
67~ Do you like it when your partner moans and/or is vocal during sex?
*** Random Questions ***
Will you kiss after your partner has gone down on you? Swallow or spit semen?
84~ How do you feel about reading/listening to adult stories?
Escort/Client Job Applicant/Hiring Manager
40~ What’s the weirdest place you’ve ever had sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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?
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…
Nurse/Patient Celebrity/Fan
61~ How willing would you be to try new sexual positions?
13~ Is there a difference between, making love, having sex, and fucking?
What have you learned about yourself that you did not before this?
13- What is the craziest/scariest thing you've ever done?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
3- What Superhero or Superpower would you want to be/have?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
39~ What are your love languages?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you allow me to clean every part of your body with my soapy hands and fingers?
81~ Do you have any kinks and/or fetishes?
What is your favorite toy? Ever wanted to try a specific toy?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
8- What are your thoughts on politics?
7- What if a person smells a certain way? 8- How about smoking?
53~ How much can you tell me about the one thing you are most passionate about?
37- Do you like your name? If you could change it, what would you change it too?
Would you do it again, and would you rather 2 females or 2 males?
What have you learned about me that was new and/or surprising?
Doctor/Nurse Stripper/Client
29- How superstitious are you?
11~ Have you ever been caught by your parents or children or others while having sex?
Master/Slave Boss/Maid
27- What was/ is nickname? Does it have a meaning behind it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
The Ice Breaker Questions
22- What is your favorite childhood memory? What is your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
21~ What was the best date you ever went on? What has been the worst?
11- How about if they like a certain sports team? 12-How about drinking too much?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
30~ What's something unexpected that turns you on?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would /have you ever given your partner a lap dance and Striptease?
60~ How important is oral sex? Do you like receiving? Do you like giving?
28~ What are some things that turn on? What is your biggest turn on?
28- What are some things that people do that irritate you?
* Give a rating for each one (0-100)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Get this wrong and this could mean the end… :-) some funny, some not…
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
33- If you could visit any time period, when would you pick? Please explain why?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
17- What’s your favorite holiday? What’s your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would you ever want to be woken up with oral and/or intercourse?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
47~ What would be your dream job and why?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
51~ What tends to bring a smile to your face?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
44~ Care to share something about yourself that no one else knows about you?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
83~ How do you feel about Porn?
10- List 5 of your top pet peeves.
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)
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What would you say to prove to yourself that it was really you?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you like the “69” position? Do you prefer to be on top or bottom?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
34~ Do you like the lights on or off during sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
How about if they talk dirty and/or call you names?
That one or two things that made you go hmmmm, OMG or wow!
20- What’s your favorite candy? What’s your least favorite?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you have a favorite? Is it ok if your partner does?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
11- List at least 5 things on your bucket list. Have you done any of them already?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What is your view on sex? Meaning, When/Where/ How often/
17- Have you ever done drugs? Which ones? How often?
34- Ever been to a concert? What was your favorite? Who would you like to see?
What is your favorite position? Why?
9- Is there something you’ve always wanted to ask me but you’re afraid?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
31- If given a chance to be immortal, would you take it? Why?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
11- What's your favorite restaurant? What’s your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
51~ Are you willing to play adult games with your partner?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
42~ What’s your biggest regret in life?
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?