What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 04:29
92~ Have you ever had or have an STD? How many? What was it?
That one or two things that made you go hmmmm, OMG or wow!
How well do you know me? And some of your thoughts about me
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
84~ How do you feel about reading/listening to adult stories?
What is your favorite position? Why?
Why do I feel like I want to suck a big dick after injecting meth?
Will you cheat again? How can, you be sure? Define what cheating is to you.
What would you say to prove to yourself that it was really you?
*** Questions about Relationships/Past ***
How do you get a teenage boy to care about hygiene?
28~ What are some things that turn on? What is your biggest turn on?
19- What’s your favorite fairytale? What’s your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Do you think this brought you closer together?
18- How often do you drink alcohol? What is your favorite drink?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
When Kundalini is awakened accidentally, what can be done?
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)
9- If you could have three wishes, what would they be? Why?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Family Relation Age Play
Any that are a turn off?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
71~ Would you give your partner a hand or foot job? Would you receive one?
Would you ever want to be woken up with oral and/or intercourse?
What is your secret to glowing skin?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
*** Deal Breaker Questions ***
22~ What is the best pickup line anyone has ever used on you? What was the worst?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
The Ice Breaker Questions
15- What bad habit do you wish you could quit? Do you have any addictions?
Prisoner/Prison Guard Landlord/Tenant
How can I remove decimals in math?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12- What’s your favorite food? What’s your least favorite?
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13~ Is there a difference between, making love, having sex, and fucking?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
10- What is your favorite family tradition? What’s your least favorite?
Where are the gay people in India?
I would allow you to do it… What would you do to me?
Would you read them together?
4- For a pet, Cat, dog or other?
How can I get over a break up?
What have you learned about me that was new and/or surprising?
61~ How willing would you be to try new sexual positions?
What is your favorite toy? Ever wanted to try a specific toy?
9~ How many times over your lifetime do you think you have had sex so far?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
14- What's your favorite dessert? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
If you win, what will you make them do?
89~ Do you like taking showers together?
What have you learned about yourself that you did not before this?
13- What’s your favorite drink? What’s your least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13- What is the craziest/scariest thing you've ever done?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
20- What’s your favorite candy? What’s your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Do you have a favorite? Is it ok if your partner does?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
19~ Who/when was your first “heartbreak”?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
34- Ever been to a concert? What was your favorite? Who would you like to see?
52~ Are you willing to make “those types” of bets with your partner?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
51~ What tends to bring a smile to your face?
Any that are a turn off?
How old are you? Male or Female?
37- Do you like your name? If you could change it, what would you change it too?
33- Beach or Mountains? Or is there another place to like better?
8- What's your favorite flavor of ice cream? Do you a least favorite?
18~ Who/when was your first “crush”?
What is your view on sex? Meaning, When/Where/ How often/
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?
53~ How much can you tell me about the one thing you are most passionate about?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
21~ What was the best date you ever went on? What has been the worst?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Does the thought excite you? Care to share?
34~ Do you like the lights on or off during sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
3- What’s your favorite smell? Do you a least favorite?
29- How superstitious are you?
Nurse/Patient Celebrity/Fan
30~ What's something unexpected that turns you on?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
62~ Have you used adult toys?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Please share Did you stop?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
1- What’s your favorite animal? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
3- What Superhero or Superpower would you want to be/have?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What do you dislike about me? I asked you to be 100% honest.
52~ What are your hobbies?
38~ Share your most embarrassing sexual memory?
83~ How do you feel about Porn?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Teacher/Student Stranger/One Night Stand
82~ Do you have any fantasies involving Role-Playing?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
21- What's your favorite way to spend a weekend or time off?
9- What’s your favorite season and why? What’s your least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
10- List 5 of your top pet peeves.
Master/Slave Boss/Maid
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
8- What are your thoughts on politics?
Over time has your thoughts on sex changed?
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
29~ What are some things that turn you off? What is your biggest turn off?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
80~ Share your top three fantasies/desires. (Be detailed) 😊
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Nothing too Serious
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Would /have you ever given your partner a lap dance and Striptease?
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?
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What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
If yes, what?
51~ Are you willing to play adult games with your partner?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
36- Do you play video games? What is your favorite? 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?
81~ Do you have any kinks and/or fetishes?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you do it again, and would you rather 2 females or 2 males?
44~ Care to share something about yourself that no one else knows about you?
50~ How many children do you have? What are their ages?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
22- What is your favorite childhood memory? What is 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…
2- What’s your favorite color? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
60~ How important is oral sex? Do you like receiving? Do you like giving?
19- Do/have you smoked? What do you prefer? How often?
6- Do you have dreams? Can you remember them? What do you usually dream about?
27- What was/ is nickname? Does it have a meaning behind it?
Have you ever? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
Would you mind if your partner watched it? How about together vs alone?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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?
Escort/Client Job Applicant/Hiring Manager
7-What do I do in bed that drives you wild? How about, what turns you off?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
3- Should Pluto still be considered a planet? 4- How about smoking?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
How many times do you think you have “made love”?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
32- What's your greatest talent? Can I see it right now?
*** What’s Your Favorite…? ***
Do you like it when they show and tell you what they want?
65~ Describe the best orgasm you’ve ever had? Care to share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
How about if they talk dirty and/or call you names?
92~ Everyone needs a “safe” word. What is yours?
40~ What’s the weirdest place you’ve ever had sex?
13- How about having a certain hair cut/style?
You know that I will be 100% truthful, so ask.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
39~ What are your love languages?
Model/Photographer Police/Criminal
If you say it, I will stop, and we can talk about it when you are ready.
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,
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Get this wrong and this could mean the end… :-) some funny, some not…
22- Do you have any birth marks? How about scars? Care to share how you got them?
70~ Would/do you have/like anal sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
26~ What side of the bed do you sleep on?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
31- If given a chance to be immortal, would you take it? Why?
47~ What would be your dream job and why?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
How many partners have you had oral sex with? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
*** Random Questions ***
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…
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
*** Questions About Me ***
23- What is your dream job? What was it as a child?
48~ Have you ever paid or been paid for sex?
7- What are your thoughts on religion? Is there an afterlife?
36~ What is your favorite time of day to have sex/make love?
11- What's your favorite restaurant? What’s your least favorite?
Doctor/Nurse Stripper/Client
12- What is the weirdest thing you've ever eaten?
17- Have you ever done drugs? Which ones? How often?
28- What are some things that people do that irritate you?
17- What’s your favorite holiday? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
1- What was your first impression of me? Has it changed?
10~ How many dates are necessary before you to have sex with someone?
Do you watch it? What is your favorite?
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Repairman/Lonely Wife Virgin/Experienced
25~ How do you feel about PDA? (Public Display of Affection)
15~ Have you ever been “in love”? Who? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
76~ Have you had a threesome? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
11~ Have you ever been caught by your parents or children or others while having sex?
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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
5- Have you ever been hypnotized? Would you allow yourself to be?
11- How about if they like a certain sports team? 12-How about drinking too much?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
42~ What’s your biggest regret in life?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
49~ How many times have you been married? Why did they end?
* Give a rating for each one (0-100)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What was the longest? What was the shortest?
(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…)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)