What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 03:16
Would you do it again, and would you rather 2 females or 2 males?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
What should I do to stop being angered easily?
9- What’s your favorite season and why? What’s your least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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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3- Should Pluto still be considered a planet? 4- How about smoking?
Over time has your thoughts on sex changed?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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Do you like the “69” position? Do you prefer to be on top or bottom?
81~ Do you have any kinks and/or fetishes?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How come Taiwan is LGBT friendly, yet Japan and South Korea are not?
19- What’s your favorite fairytale? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What is your favorite position? Why?
Are there any penalties for bestiality in the USA and laws prohibiting it?
I would allow you to do it… What would you do to me?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
18~ Who/when was your first “crush”?
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Repairman/Lonely Wife Virgin/Experienced
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
If you say it, I will stop, and we can talk about it when you are ready.
Do most men prefer curvy women or skinny women?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
18- How often do you drink alcohol? What is your favorite drink?
What is the Replika app, and how does it work?
How many partners have you had oral sex with? Who? Care to Share?
What would you say to prove to yourself that it was really you?
15~ Have you ever been “in love”? Who? Care to Share?
Why are men so attracted to big breasts?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
42~ What’s your biggest regret in life?
65~ Describe the best orgasm you’ve ever had? Care to share?
2- What’s your favorite color? Do you a least favorite?
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?
Do you think this brought you closer together?
How old are you? Male or Female?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What are some common examples of condescending behavior?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Prisoner/Prison Guard Landlord/Tenant
14- What is an embarrassing moment in your life? How about your most embarrassing?
Which current F1 drivers should switch teams based on historical patterns?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
12- What’s your favorite food? What’s your least favorite?
What have you learned about me that was new and/or surprising?
Are there any real-life examples of prisoners who escaped from hospitals and were never caught?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
82~ Do you have any fantasies involving Role-Playing?
14- What's your favorite dessert? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
29- How superstitious are you?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
5- Have you ever been hypnotized? Would you allow yourself to be?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
3- What Superhero or Superpower would you want to be/have?
39~ What are your love languages?
33- If you could visit any time period, when would you pick? Please explain why?
10- What is your favorite family tradition? What’s your least favorite?
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
51~ What tends to bring a smile to your face?
Can you Deep Throat? Do you like the taste of yourself?
80~ Share your top three fantasies/desires. (Be detailed) 😊
10~ How many dates are necessary before you to have sex with someone?
If YES, was it with 2 men or 2 women? Did you enjoy it?
61~ How willing would you be to try new sexual positions?
Master/Slave Boss/Maid
If yes, what?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
9- If you could have three wishes, what would they be? Why?
28- What are some things that people do that irritate you?
30~ What's something unexpected that turns you on?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Teacher/Student Stranger/One Night Stand
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
71~ Would you give your partner a hand or foot job? Would you receive one?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
15- What's your favorite saying? What word or phrase is your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
11- What's your favorite restaurant? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
That one or two things that made you go hmmmm, OMG or wow!
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you have a favorite? Is it ok if your partner does?
31- If given a chance to be immortal, would you take it? Why?
How about if they talk dirty and/or call you names?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
49~ How many times have you been married? Why did they end?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
21- What's your favorite way to spend a weekend or time off?
1~ How old were you when you had your first kiss? Who? Care to Share?
Please share Did you stop?
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?
32- What's your greatest talent? Can I see it right now?
23- What is your dream job? What was it as a child?
44~ Care to share something about yourself that no one else knows about you?
22- Do you have any birth marks? How about scars? Care to share how you got them?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
16~ Do you believe in “soulmates”? Have you found yours? 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?
You know that I will be 100% truthful, so ask.
13~ Is there a difference between, making love, having sex, and fucking?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
26~ What side of the bed do you sleep on?
12- What is the weirdest thing you've ever eaten?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would you read them together?
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)
Escort/Client Job Applicant/Hiring Manager
What have you learned about yourself that you did not before this?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
29~ What are some things that turn you off? What is your biggest turn off?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What do you dislike about me? I asked you to be 100% honest.
What’s the longest time you gone without having sex, after, having it? How much time between the others?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
89~ Do you like taking showers together?
How many times do you think you have “made love”?
Nurse/Patient Celebrity/Fan
38~ Share your most embarrassing sexual memory?
27- What was/ is nickname? Does it have a meaning behind it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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…
28~ What are some things that turn on? What is your biggest turn on?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Get this wrong and this could mean the end… :-) some funny, some not…
Will you cheat again? How can, you be sure? Define what cheating is to you.
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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?
*** Questions about Relationships/Past ***
92~ Everyone needs a “safe” word. What is yours?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Model/Photographer Police/Criminal
10- List 5 of your top pet peeves.
The Ice Breaker Questions
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
How well do you know me? And some of your thoughts about me
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?
Family Relation Age Play
54~ Would you ever go skinny dipping 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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Would you mind if your partner watched it? How about together vs alone?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
76~ Have you had a threesome? Care to Share?
(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…)
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
*** Questions About Me ***
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
9~ How many times over your lifetime do you think you have had sex so far?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
50~ How many children do you have? What are their ages?
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…
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
5~ When you first started having sex, was it what you thought it would be?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
8- What's your favorite flavor of ice cream? Do you a least favorite?
Doctor/Nurse Stripper/Client
24~ What are your expectations in a relationship? (I know a very big question, take your time)
19~ Who/when was your first “heartbreak”?
11- List at least 5 things on your bucket list. Have you done any of them already?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
1- What was your first impression of me? Has it changed?
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?
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?
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37- Do you like your name? If you could change it, what would you change it too?
4- For a pet, Cat, dog or other?
Any that are a turn off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
17- Have you ever done drugs? Which ones? How often?
1- What’s your favorite animal? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Nothing too Serious
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** Random Questions ***
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
21~ What was the best date you ever went on? What has been the worst?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
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?
83~ How do you feel about Porn?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
52~ What are your hobbies?
*** What’s Your Favorite…? ***
13- How about having a certain hair cut/style?
Would /have you ever given your partner a lap dance and Striptease?
48~ Do you have any siblings? Are you close to your family?
7- What are your thoughts on religion? Is there an afterlife?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
36~ What is your favorite time of day to have sex/make love?
Do you like it when they show and tell you what they want?
7- What if a person smells a certain way? 8- How about smoking?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
92~ Have you ever had or have an STD? How many? What was it?
Would you ever want to be woken up with oral and/or intercourse?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
34~ Do you like the lights on or off during sex?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What was the longest? What was the shortest?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you watch it? What is your favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
49~ If you could, would you want to be the opposite sex for a day, week, or year?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
8- What are your thoughts on politics?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
62~ Have you used adult toys?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
84~ How do you feel about reading/listening to adult stories?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
60~ How important is oral sex? Do you like receiving? Do you like giving?
11~ Have you ever been caught by your parents or children or others while having sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
25~ How do you feel about PDA? (Public Display of Affection)
15- What bad habit do you wish you could quit? Do you have any addictions?
3- What’s your favorite smell? Do you a least favorite?
51~ Are you willing to play adult games with your partner?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
47~ What would be your dream job and why?
Does the thought excite you? Care to share?
53~ How much can you tell me about the one thing you are most passionate about?
* Give a rating for each one (0-100)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
If you win, what will you make them do?
Any that are a turn off?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
Have you ever? Care to Share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What is your view on sex? Meaning, When/Where/ How often/
70~ Would/do you have/like anal sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
*** Deal Breaker Questions ***
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
22- What is your favorite childhood memory? What is your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
18- What’s your favorite way to relax after a long day? What’s your least favorite?