What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 13:44
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
18~ Who/when was your first “crush”?
How many times do you think you have “made love”?
Why do nice guys rarely or never win?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
48~ Do you have any siblings? Are you close to your family?
(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…)
What does the Bible say about the Antichrist? How will we know when he arrives on the scene?
52~ Are you willing to make “those types” of bets with your partner?
Over time has your thoughts on sex changed?
29- How superstitious are you?
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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.
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
39~ What are your love languages?
How did you become popular in school?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
10- What is your favorite family tradition? What’s your least favorite?
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What are some hard rock or heavy metal bands that are overrated?
23- What is your dream job? What was it as a child?
32- What's your greatest talent? Can I see it right now?
5~ When you first started having sex, was it what you thought it would be?
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Would you do it again, and would you rather 2 females or 2 males?
25~ How do you feel about PDA? (Public Display of Affection)
22- Do you have any birth marks? How about scars? Care to share how you got them?
37- Do you like your name? If you could change it, what would you change it too?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
*** What’s Your Favorite…? ***
I'm pretty sure that my dog is transgender, how would I go about transitioning it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
1~ How old were you when you had your first kiss? Who? Care to Share?
What is the gayest experience you have seen in prison?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
53~ How much can you tell me about the one thing you are most passionate about?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Why do some of those who believe in a god refuse to consider the possibility they could be wrong?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Repairman/Lonely Wife Virgin/Experienced
Why is it so hard to date nowadays?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Doctor/Nurse Stripper/Client
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
14- What's your favorite dessert? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Please share Did you stop?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
7- What if a person smells a certain way? 8- How about smoking?
How old are you? Male or Female?
89~ Do you like taking showers together?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
22- What is your favorite childhood memory? What is your least favorite?
13- How about having a certain hair cut/style?
*** Random Questions ***
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you like it when they show and tell you what they want?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Do you think this brought you closer together?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Nothing too Serious
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
What is your favorite position? Why?
82~ Do you have any fantasies involving Role-Playing?
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…
12- What’s your favorite food? What’s your least favorite?
Would you read them together?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
3- What Superhero or Superpower would you want to be/have?
92~ Have you ever had or have an STD? How many? What was it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Have you ever? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
28~ What are some things that turn on? What is your biggest turn on?
65~ Describe the best orgasm you’ve ever had? Care to share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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,
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
36~ What is your favorite time of day to have sex/make love?
34~ Do you like the lights on or off during sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
17- Have you ever done drugs? Which ones? How often?
Prisoner/Prison Guard Landlord/Tenant
9- Is there something you’ve always wanted to ask me but you’re afraid?
18- How often do you drink alcohol? What is your favorite drink?
If you win, what will you make them do?
61~ How willing would you be to try new sexual positions?
92~ Everyone needs a “safe” word. What is yours?
9- What’s your favorite season and why? What’s your least favorite?
How well do you know me? And some of your thoughts about me
49~ If you could, would you want to be the opposite sex for a day, week, or year?
51~ What tends to bring a smile to your face?
27- What was/ is nickname? Does it have a meaning behind it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
11- What's your favorite restaurant? What’s your least favorite?
8- What are your thoughts on politics?
If you say it, I will stop, and we can talk about it when you are ready.
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
13- What is the craziest/scariest thing you've ever done?
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…
19- Do/have you smoked? What do you prefer? How often?
How about if they talk dirty and/or call you names?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
44~ Care to share something about yourself that no one else knows about you?
* Give a rating for each one (0-100)
Master/Slave Boss/Maid
19- What’s your favorite fairytale? What’s your least favorite?
10~ How many dates are necessary before you to have sex with someone?
20- What’s your favorite candy? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
Model/Photographer Police/Criminal
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
7-What do I do in bed that drives you wild? How about, what turns you off?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13~ Is there a difference between, making love, having sex, and fucking?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
19~ Who/when was your first “heartbreak”?
52~ What are your hobbies?
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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
*** Questions about Relationships/Past ***
50~ How many children do you have? What are their ages?
What have you learned about yourself that you did not before this?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Any that are a turn off?
28- What are some things that people do that irritate you?
You know that I will be 100% truthful, so ask.
81~ Do you have any kinks and/or fetishes?
9- If you could have three wishes, what would they be? Why?
31- If given a chance to be immortal, would you take it? Why?
17- What’s your favorite holiday? What’s your least favorite?
30~ What's something unexpected that turns you on?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
What was the longest? What was the shortest?
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?
4- For a pet, Cat, dog or other?
*** Questions About Me ***
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
33- Beach or Mountains? Or is there another place to like better?
Any that are a turn off?
That one or two things that made you go hmmmm, OMG or wow!
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
8- What's your favorite flavor of ice cream? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you ever want to be woken up with oral and/or intercourse?
What would you say to prove to yourself that it was really you?
13- What’s your favorite drink? What’s your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
11- List at least 5 things on your bucket list. Have you done any of them already?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
7- What are your thoughts on religion? Is there an afterlife?
70~ Would/do you have/like anal sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
38~ Share your most embarrassing sexual memory?
Would you mind if your partner watched it? How about together vs alone?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you watch it? What is your favorite?
Do you have a favorite? Is it ok if your partner does?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
*** Deal Breaker Questions ***
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
11- How about if they like a certain sports team? 12-How about drinking too much?
The Ice Breaker Questions
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
84~ How do you feel about reading/listening to adult stories?
What is your favorite toy? Ever wanted to try a specific toy?
21~ What was the best date you ever went on? What has been the worst?
Does the thought excite you? Care to share?
Nurse/Patient Celebrity/Fan
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Do you like the “69” position? Do you prefer to be on top or bottom?
76~ Have you had a threesome? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
What is your view on sex? Meaning, When/Where/ How often/
If YES, was it with 2 men or 2 women? Did you enjoy it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
12- What is the weirdest thing you've ever eaten?
42~ What’s your biggest regret in life?
83~ How do you feel about Porn?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Escort/Client Job Applicant/Hiring Manager
11~ Have you ever been caught by your parents or children or others while having sex?
What have you learned about me that was new and/or surprising?
21- What's your favorite way to spend a weekend or time off?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
49~ How many times have you been married? Why did they end?
What do you dislike about me? I asked you to be 100% honest.
48~ Have you ever paid or been paid for sex?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
2- What’s your favorite color? Do you a least favorite?
26~ What side of the bed do you sleep on?
Get this wrong and this could mean the end… :-) some funny, some not…
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
1- What’s your favorite animal? Do you a least favorite?
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)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Can you Deep Throat? Do you like the taste of yourself?
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?
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?
10- List 5 of your top pet peeves.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
67~ Do you like it when your partner moans and/or is vocal during sex?
How many partners have you had oral sex with? Who? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If yes, what?
34- Ever been to a concert? What was your favorite? Who would you like to see?
71~ Would you give your partner a hand or foot job? Would you receive one?
29~ What are some things that turn you off? What is your biggest turn off?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
40~ What’s the weirdest place you’ve ever had sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
14- What is an embarrassing moment in your life? How about your most embarrassing?
3- What’s your favorite smell? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
9~ How many times over your lifetime do you think you have had sex so far?
I would allow you to do it… What would you do to me?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
51~ Are you willing to play adult games with your partner?
47~ What would be your dream job and why?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Family Relation Age Play
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?
62~ Have you used adult toys?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
15~ Have you ever been “in love”? Who? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?