What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 01:03
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
5- Have you ever been hypnotized? Would you allow yourself to be?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What have you learned about me that was new and/or surprising?
Model/Photographer Police/Criminal
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What are the signs of covert narcissistic abuse that most people miss?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
47~ What would be your dream job and why?
Why do narcissists want to hurt your feelings, even after they discard you?
62~ Have you used adult toys?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
How old are you? Male or Female?
Why do I keep waking up at 4 AM?
7- What are your thoughts on religion? Is there an afterlife?
What was the longest? What was the shortest?
33- If you could visit any time period, when would you pick? Please explain why?
On Which Part of the Body Might One Wear Winklepickers? - Slate Magazine
3- What was the most surprising thing you’ve learned about me throughout our relationship?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Do you like it when they show and tell you what they want?
19~ Who/when was your first “heartbreak”?
14- What's your favorite dessert? Do you a least favorite?
21- What's your favorite way to spend a weekend or time off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What did your mother say that made your jaw drop?
44~ Care to share something about yourself that no one else knows about you?
42~ What’s your biggest regret in life?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
76~ Have you had a threesome? Care to Share?
Nothing too Serious
84~ How do you feel about reading/listening to adult stories?
Doctor/Nurse Stripper/Client
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
48~ Have you ever paid or been paid for sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
What thing happened to you as a child that you haven’t let go of to this day?
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?
11- What's your favorite restaurant? What’s your least favorite?
What would you say to prove to yourself that it was really you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
(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…)
65~ Describe the best orgasm you’ve ever had? Care to share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Family Relation Age Play
1- What was your first impression of me? Has it changed?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
*** Questions About Me ***
20- What’s your favorite candy? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
34- Ever been to a concert? What was your favorite? Who would you like to see?
11~ Have you ever been caught by your parents or children or others while having sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Any that are a turn off?
What have you learned about yourself that you did not before this?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
1- What’s your favorite animal? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Does the thought excite you? Care to share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
7- What if a person smells a certain way? 8- How about smoking?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
13- How about having a certain hair cut/style?
82~ Do you have any fantasies involving Role-Playing?
92~ Have you ever had or have an STD? How many? What was it?
Over time has your thoughts on sex changed?
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?
How many partners have you had oral sex with? Who? Care to Share?
83~ How do you feel about Porn?
50~ How many children do you have? What are their ages?
Master/Slave Boss/Maid
Will you cheat again? How can, you be sure? Define what cheating is to you.
70~ Would/do you have/like anal sex?
56~ Would you ever go to a strip club with your partner? Have you ever been? 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?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
23- What is your dream job? What was it as a child?
25~ How do you feel about PDA? (Public Display of Affection)
Do you have a favorite? Is it ok if your partner does?
11- List at least 5 things on your bucket list. Have you done any of them already?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
18~ Who/when was your first “crush”?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
9- What’s your favorite season and why? What’s your least favorite?
21~ What was the best date you ever went on? What has been the worst?
49~ How many times have you been married? Why did they end?
53~ How much can you tell me about the one thing you are most passionate about?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
52~ Are you willing to make “those types” of bets with your partner?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
10- List 5 of your top pet peeves.
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
15- What's your favorite saying? What word or phrase is your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
8- What are your thoughts on politics?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
15~ Have you ever been “in love”? Who? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
22- What is your favorite childhood memory? What is your least favorite?
36~ What is your favorite time of day to have sex/make love?
19- Do/have you smoked? What do you prefer? How often?
28~ What are some things that turn on? What is your biggest turn on?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Teacher/Student Stranger/One Night Stand
17- What’s your favorite holiday? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
35- Do you like playing board or cards game? What is your favorite? 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?
34~ Do you like the lights on or off during sex?
If you win, what will you make them do?
4- For a pet, Cat, dog or other?
*** Random Questions ***
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
51~ Are you willing to play adult games with your partner?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
18- How often do you drink alcohol? What is your favorite drink?
That one or two things that made you go hmmmm, OMG or wow!
5~ When you first started having sex, was it what you thought it would be?
If YES, was it with 2 men or 2 women? Did you enjoy 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?
9~ How many times over your lifetime do you think you have had sex so far?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
*** Questions about Relationships/Past ***
39~ What are your love languages?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Please share Did you stop?
Would you mind if your partner watched it? How about together vs alone?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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,
How about if they talk dirty and/or call you names?
12- What’s your favorite food? What’s your least favorite?
3- What Superhero or Superpower would you want to be/have?
29~ What are some things that turn you off? What is your biggest turn off?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Repairman/Lonely Wife Virgin/Experienced
If yes, what?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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…
What is your favorite toy? Ever wanted to try a specific toy?
Escort/Client Job Applicant/Hiring Manager
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
61~ How willing would you be to try new sexual positions?
31- If given a chance to be immortal, would you take it? Why?
81~ Do you have any kinks and/or fetishes?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
15- What bad habit do you wish you could quit? Do you have any addictions?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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)
19- What’s your favorite fairytale? What’s your least favorite?
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?
10~ How many dates are necessary before you to have sex with someone?
How many times do you think you have “made love”?
I would allow you to do it… What would you do to me?
17- Have you ever done drugs? Which ones? How often?
*** What’s Your Favorite…? ***
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
You know that I will be 100% truthful, so ask.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
*** Deal Breaker Questions ***
Any that are a turn off?
Can you Deep Throat? Do you like the taste of yourself?
What do you dislike about me? I asked you to be 100% honest.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would /have you ever given your partner a lap dance and Striptease?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
22- Do you have any birth marks? How about scars? Care to share how you got them?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
51~ What tends to bring a smile to your face?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
54~ Would you ever go skinny dipping 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?
Nurse/Patient Celebrity/Fan
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
The Ice 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?
* Give a rating for each one (0-100)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Have you ever? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
30~ What's something unexpected that turns you on?
13- What is the craziest/scariest thing you've ever done?
28- What are some things that people do that irritate you?
What is your view on sex? Meaning, When/Where/ How often/
92~ Everyone needs a “safe” word. What is yours?
13~ Is there a difference between, making love, having sex, and fucking?
Do you think this brought you closer together?
26~ What side of the bed do you sleep on?
8- What's your favorite flavor of ice cream? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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?
Do you watch it? What is 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…
7-What do I do in bed that drives you wild? How about, what turns you off?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
89~ Do you like taking showers together?
33- Beach or Mountains? Or is there another place to like better?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What is your favorite position? Why?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
27- What was/ is nickname? Does it have a meaning behind it?
36- Do you play video games? What is your favorite? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Would you do it again, and would you rather 2 females or 2 males?
48~ Do you have any siblings? Are you close to your family?
2- What’s your favorite color? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you read them together?
How well do you know me? And some of your thoughts about me
60~ How important is oral sex? Do you like receiving? Do you like giving?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
9- If you could have three wishes, what would they be? Why?
32- What's your greatest talent? Can I see it right now?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
1~ How old were you when you had your first kiss? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
If NO, would you ever have one? Would it be with 2 men or 2 women?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
3- What’s your favorite smell? Do you a least favorite?
10- What is your favorite family tradition? What’s your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
13- What’s your favorite drink? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
52~ What are your hobbies?
Would you ever want to be woken up with oral and/or intercourse?
37- Do you like your name? If you could change it, what would you change it too?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?