What is the most interesting question you can ask to get to know someone?
14.06.2025 04:57
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
* Give a rating for each one (0-100)
Model/Photographer Police/Criminal
33- Beach or Mountains? Or is there another place to like better?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
3- Should Pluto still be considered a planet? 4- How about smoking?
What is the most memorable thing that happened in your college days?
81~ Do you have any kinks and/or fetishes?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Why do I feel worthless most of the time?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
*** Random Questions ***
Why did Donald Trump and Melania Trump sleep in different rooms?
Please share Did you stop?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
9 Things Women’s Health Doctors Would Never Do - HuffPost
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
If YES, was it with 2 men or 2 women? Did you enjoy it?
Have you ever? Care to Share?
How Fast Are You Aging? Neuroscience Says These 3 Simple Tests Can Tell You - Inc.com
7- What if a person smells a certain way? 8- How about smoking?
Do you think this brought you closer together?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How do great movie moments influence how people handle real-life moral dilemmas?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
61~ How willing would you be to try new sexual positions?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
What's an underrated/unknown novel or series that you think deserves more attention?
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?
That one or two things that made you go hmmmm, OMG or wow!
10- What is your favorite family tradition? What’s your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
Master/Slave Boss/Maid
How do you get a teenage boy to care about hygiene?
Family Relation Age Play
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What made you recently say to yourself, “Wait. Really?”
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
*** Questions About Me ***
Do guys prefer big boobs or small boobs? Why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
13- What is the craziest/scariest thing you've ever done?
11~ Have you ever been caught by your parents or children or others while having sex?
What movies have not aged well?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
25~ How do you feel about PDA? (Public Display of Affection)
60~ How important is oral sex? Do you like receiving? Do you like giving?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
26~ What side of the bed do you sleep on?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
10- List 5 of your top pet peeves.
Over time has your thoughts on sex changed?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What have you learned about me that was new and/or surprising?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Do you like the “69” position? Do you prefer to be on top or bottom?
Would you mind if your partner watched it? How about together vs alone?
8- What are your thoughts on politics?
(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…)
If yes, what?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
4- For a pet, Cat, dog or other?
What have you learned about yourself that you did not before this?
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…
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
29~ What are some things that turn you off? What is your biggest turn off?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
30~ What's something unexpected that turns you on?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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)
Do you like it when they show and tell you what they want?
2- What’s your favorite color? 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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13- How about having a certain hair cut/style?
9~ How many times over your lifetime do you think you have had sex so far?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Get this wrong and this could mean the end… :-) some funny, some not…
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?
92~ Everyone needs a “safe” word. What is yours?
7- What are your thoughts on religion? Is there an afterlife?
34~ Do you like the lights on or off during sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
You know that I will be 100% truthful, so ask.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
76~ Have you had a threesome? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
7-What do I do in bed that drives you wild? How about, what turns you off?
How well do you know me? And some of your thoughts about me
How about if they talk dirty and/or call you names?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
13- What’s your favorite drink? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What would you say to prove to yourself that it was really you?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
How many partners have you had oral sex with? Who? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
11- How about if they like a certain sports team? 12-How about drinking too much?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
22- Do you have any birth marks? How about scars? Care to share how you got them?
17- What’s your favorite holiday? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
Would /have you ever given your partner a lap dance and Striptease?
What was the longest? What was the shortest?
*** Deal Breaker Questions ***
19- What’s your favorite fairytale? What’s your least favorite?
49~ How many times have you been married? Why did they end?
Nurse/Patient Celebrity/Fan
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you ever want to be woken up with oral and/or intercourse?
15- What bad habit do you wish you could quit? Do you have any addictions?
50~ How many children do you have? What are their ages?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
3- What Superhero or Superpower would you want to be/have?
21~ What was the best date you ever went on? What has been the worst?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
44~ Care to share something about yourself that no one else knows about you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How old are you? Male or Female?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
11- What's your favorite restaurant? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
1- What was your first impression of me? Has it changed?
10~ How many dates are necessary before you to have sex with someone?
9- If you could have three wishes, what would they be? Why?
36- Do you play video games? What is your favorite? Do you a least favorite?
28- What are some things that people do that irritate you?
12- What is the weirdest thing you've ever eaten?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
51~ Are you willing to play adult games with your partner?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
36~ What is your favorite time of day to have sex/make love?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
67~ Do you like it when your partner moans and/or is vocal during sex?
37- Do you like your name? If you could change it, what would you change it too?
Any that are a turn off?
1- What’s your favorite animal? Do you a least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
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,
27- What was/ is nickname? Does it have a meaning behind it?
89~ Do you like taking showers together?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
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?
83~ How do you feel about Porn?
32- What's your greatest talent? Can I see it right now?
48~ Do you have any siblings? Are you close to your family?
19- Do/have you smoked? What do you prefer? How often?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What is your favorite position? Why?
How many times do you think you have “made love”?
18~ Who/when was your first “crush”?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Doctor/Nurse Stripper/Client
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
If you say it, I will stop, and we can talk about it when you are ready.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
52~ What are your hobbies?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** What’s Your Favorite…? ***
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
The Ice Breaker Questions
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
42~ What’s your biggest regret in life?
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?
5~ When you first started having sex, was it what you thought it would be?
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?
19~ Who/when was your first “heartbreak”?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Nothing too Serious
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
12- What’s your favorite food? What’s your least favorite?
3- What’s your favorite smell? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
Would you do it again, and would you rather 2 females or 2 males?
38~ Share your most embarrassing sexual memory?
47~ What would be your dream job and why?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
18- How often do you drink alcohol? What is your favorite drink?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
23- What is your dream job? What was it as a child?
39~ What are your love languages?
Prisoner/Prison Guard Landlord/Tenant
64~ When was your very first orgasm? When was your first from having sex? Care to share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
I would allow you to do it… What would you do to me?
65~ Describe the best orgasm you’ve ever had? Care to share?
Escort/Client Job Applicant/Hiring Manager
Can you Deep Throat? Do you like the taste of yourself?
22- What is your favorite childhood memory? What is your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
If you win, what will you make them do?
Repairman/Lonely Wife Virgin/Experienced
21- What's your favorite way to spend a weekend or time off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What is your favorite toy? Ever wanted to try a specific toy?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
80~ Share your top three fantasies/desires. (Be detailed) 😊
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
If NO, would you ever have one? Would it be with 2 men or 2 women?
Would you read them together?
9- What’s your favorite season and why? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
20- What’s your favorite candy? What’s your least favorite?
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…
Do you watch it? What is your favorite?
Does the thought excite you? Care to share?
14- What's your favorite dessert? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
82~ Do you have any fantasies involving Role-Playing?
11- List at least 5 things on your bucket list. Have you done any of them already?
15~ Have you ever been “in love”? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
29- How superstitious are you?
5- Have you ever been hypnotized? Would you allow yourself to be?
51~ What tends to bring a smile to your face?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Teacher/Student Stranger/One Night Stand
92~ Have you ever had or have an STD? How many? What was it?
Do you have a favorite? Is it ok if your partner does?
62~ Have you used adult toys?
*** Questions about Relationships/Past ***
What is your view on sex? Meaning, When/Where/ How often/
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
17- Have you ever done drugs? Which ones? How often?
53~ How much can you tell me about the one thing you are most passionate about?
Any that are a turn off?
84~ How do you feel about reading/listening to adult stories?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
28~ What are some things that turn on? What is your biggest turn on?