What is the most interesting question you can ask to get to know someone?
10.06.2025 08:38

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