What is the most interesting question you can ask to get to know someone?
09.06.2025 02:46

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