What is the most interesting question you can ask to get to know someone?
Last Updated: 28.06.2025 06:43
Model/Photographer Police/Criminal
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Do you like it when they show and tell you what they want?
33- If you could visit any time period, when would you pick? Please explain why?
29~ What are some things that turn you off? What is your biggest turn off?
Would you allow me to clean every part of your body with my soapy hands and fingers?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
3- What Superhero or Superpower would you want to be/have?
38~ Share your most embarrassing sexual memory?
What is the Replika app, and how does it work?
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?
Prisoner/Prison Guard Landlord/Tenant
Family Relation Age Play
84~ How do you feel about reading/listening to adult stories?
35- Do you like playing board or cards game? What is your favorite? Do you a 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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16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Can you Deep Throat? Do you like the taste of yourself?
Have you ever? Care to Share?
How well do you know me? And some of your thoughts about me
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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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?
21- What's your favorite way to spend a weekend or time off?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Celebrity breast cancer announcements highlight rising rates in young women - NBC News
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
8- What are your thoughts on politics?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
52~ Are you willing to make “those types” of bets with your partner?
89~ Do you like taking showers together?
When the sun dies, could life survive on the Jupiter ocean moon Europa? - Space
9- What’s your favorite season and why? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What is your favorite toy? Ever wanted to try a specific toy?
65~ Describe the best orgasm you’ve ever had? Care to share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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7- What are your thoughts on religion? Is there an afterlife?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
36- Do you play video games? What is your favorite? Do you a least favorite?
Why do so many autistic adults deal with self-hatred?
7-What do I do in bed that drives you wild? How about, what turns you off?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Get this wrong and this could mean the end… :-) some funny, some not…
30~ What's something unexpected that turns you on?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
15- What bad habit do you wish you could quit? Do you have any addictions?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Does the thought excite you? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
27- What was/ is nickname? Does it have a meaning behind it?
15~ Have you ever been “in love”? Who? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Do you think this brought you closer together?
10~ How many dates are necessary before you to have sex with someone?
15- What's your favorite saying? What word or phrase is your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you ever want to be woken up with oral and/or intercourse?
11~ Have you ever been caught by your parents or children or others while having sex?
Nurse/Patient Celebrity/Fan
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
12- What’s your favorite food? What’s your least favorite?
Master/Slave Boss/Maid
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
80~ Share your top three fantasies/desires. (Be detailed) 😊
53~ How much can you tell me about the one thing you are most passionate about?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
29- How superstitious are you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
14- What is an embarrassing moment in your life? How about your most embarrassing?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
31- If given a chance to be immortal, would you take it? Why?
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?
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…
21~ What was the best date you ever went on? What has been the worst?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
(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…)
Over time has your thoughts on sex changed?
5- Have you ever been hypnotized? Would you allow yourself to be?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
20- What’s your favorite candy? What’s your least favorite?
Any that are a turn off?
71~ Would you give your partner a hand or foot job? Would you receive one?
18- How often do you drink alcohol? What is your favorite drink?
48~ Have you ever paid or been paid for sex?
92~ Have you ever had or have an STD? How many? What was it?
47~ What would be your dream job and why?
How old are you? Male or Female?
19~ Who/when was your first “heartbreak”?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
9~ How many times over your lifetime do you think you have had sex so far?
What is your favorite position? Why?
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?
40~ What’s the weirdest place you’ve ever had sex?
5~ When you first started having sex, was it what you thought it would be?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Repairman/Lonely Wife Virgin/Experienced
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
12- What is the weirdest thing you've ever eaten?
44~ Care to share something about yourself that no one else knows about you?
How many times do you think you have “made love”?
If NO, would you ever have one? Would it be with 2 men or 2 women?
14- What's your favorite dessert? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
Do you have a favorite? Is it ok if your partner does?
If you win, what will you make them do?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
42~ What’s your biggest regret in life?
28~ What are some things that turn on? What is your biggest turn on?
19- Do/have you smoked? What do you prefer? How often?
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
If you say it, I will stop, and we can talk about it when you are ready.
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
49~ How many times have you been married? Why did they end?
*** Questions about Relationships/Past ***
83~ How do you feel about Porn?
62~ Have you used adult toys?
10- What is your favorite family tradition? What’s your least favorite?
50~ How many children do you have? What are their ages?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
51~ Are you willing to play adult games with your partner?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
13- What’s your favorite drink? What’s your least favorite?
What have you learned about yourself that you did not before this?
9- If you could have three wishes, what would they be? Why?
I would allow you to do it… What would you do to me?
1- What’s your favorite animal? Do you a least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How many partners have you had oral sex with? Who? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
39~ What are your love languages?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
22- What is your favorite childhood memory? What is your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
What have you learned about me that was new and/or surprising?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
2- What’s your favorite color? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Doctor/Nurse Stripper/Client
61~ How willing would you be to try new sexual positions?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
That one or two things that made you go hmmmm, OMG or wow!
22- Do you have any birth marks? How about scars? Care to share how you got them?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
* Give a rating for each one (0-100)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Nothing too Serious
What is your view on sex? Meaning, When/Where/ How often/
19- What’s your favorite fairytale? What’s your least favorite?
*** Random Questions ***
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Any that are a turn off?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
34~ Do you like the lights on or off during sex?
Please share Did you stop?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
48~ Do you have any siblings? Are you close to your family?
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…
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
3- What’s your favorite smell? Do you a least favorite?
Would you read them together?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
1- What was your first impression of me? Has it changed?
*** Questions About Me ***
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
13- What is the craziest/scariest thing you've ever done?
37- Do you like your name? If you could change it, what would you change it too?
67~ Do you like it when your partner moans and/or is vocal during sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do you like the “69” position? Do you prefer to be on top or bottom?
26~ What side of the bed do you sleep on?
76~ Have you had a threesome? Care to Share?
28- What are some things that people do that irritate you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
92~ Everyone needs a “safe” word. What is yours?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Escort/Client Job Applicant/Hiring Manager
70~ Would/do you have/like anal sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
The Ice Breaker Questions
25~ How do you feel about PDA? (Public Display of Affection)
82~ Do you have any fantasies involving Role-Playing?
33- Beach or Mountains? Or is there another place to like better?
13~ Is there a difference between, making love, having sex, and fucking?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Do you watch it? What is your favorite?
11- What's your favorite restaurant? What’s your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
11- List at least 5 things on your bucket list. Have you done any of them already?
18~ Who/when was your first “crush”?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
*** What’s Your Favorite…? ***
24~ What are your expectations in a relationship? (I know a very big question, take your time)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
36~ What is your favorite time of day to have sex/make love?
You know that I will be 100% truthful, so ask.
60~ How important is oral sex? Do you like receiving? Do you like giving?
32- What's your greatest talent? Can I see it right now?
What was the longest? What was the shortest?
52~ What are your hobbies?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you mind if your partner watched it? How about together vs alone?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
10- List 5 of your top pet peeves.
81~ Do you have any kinks and/or fetishes?
51~ What tends to bring a smile to your face?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
17- Have you ever done drugs? Which ones? How often?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What would you say to prove to yourself that it was really you?
13- How about having a certain hair cut/style?
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?
Teacher/Student Stranger/One Night Stand
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
23- What is your dream job? What was it as a child?
*** Deal Breaker Questions ***
What do you dislike about me? I asked you to be 100% honest.
If yes, what?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
6- Do you have dreams? Can you remember them? What do you usually dream about?
4- For a pet, Cat, dog or other?
3- Should Pluto still be considered a planet? 4- How about smoking?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
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,
8- What's your favorite flavor of ice cream? Do you a least favorite?
How about if they talk dirty and/or call you names?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you do it again, and would you rather 2 females or 2 males?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?