What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 07:32
49~ If you could, would you want to be the opposite sex for a day, week, or year?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
4- For a pet, Cat, dog or other?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
In what circumstances might a chaperone be appropriate for a medical examination?
22- What is your favorite childhood memory? What is your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Do you have a favorite? Is it ok if your partner does?
Why do people say "tall, dark, and handsome" when they actually mean "tall, white, and handsome"?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
*** Deal Breaker Questions ***
Doctor/Nurse Stripper/Client
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
28- What are some things that people do that irritate you?
10~ How many dates are necessary before you to have sex with someone?
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?
3- What Superhero or Superpower would you want to be/have?
What are examples of real life forced feminization?
Teacher/Student Stranger/One Night Stand
67~ Do you like it when your partner moans and/or is vocal during sex?
Have you ever? Care to Share?
What does the Turkish word çıplak mean?
Do you think this brought you closer together?
13- What’s your favorite drink? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
Who is the greatest light welterweight boxer of all time?
3- What’s your favorite smell? Do you a least favorite?
70~ Would/do you have/like anal sex?
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?
Did you become a cuckold for your wife?
1- What’s your favorite animal? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
17- Have you ever done drugs? Which ones? How often?
Why do narcissists devour so much sugar (candy, ice cream, donuts, etc., in huge amounts at a time)?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Escort/Client Job Applicant/Hiring Manager
You know that I will be 100% truthful, so ask.
Why do men prefer women below the age of 30?
10- What is your favorite family tradition? What’s your least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
28~ What are some things that turn on? What is your biggest turn on?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
*** What’s Your Favorite…? ***
What is your view on sex? Meaning, When/Where/ How often/
Which one is better to guys, boobs or butt?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Nothing too Serious
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
9- If you could have three wishes, what would they be? Why?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Please share Did you stop?
7-What do I do in bed that drives you wild? How about, what turns you off?
That one or two things that made you go hmmmm, OMG or wow!
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If yes, what?
82~ Do you have any fantasies involving Role-Playing?
84~ How do you feel about reading/listening to adult stories?
19~ Who/when was your first “heartbreak”?
9~ How many times over your lifetime do you think you have had sex so far?
13- What is the craziest/scariest thing you've ever done?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
62~ Have you used adult toys?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Nurse/Patient Celebrity/Fan
1~ How old were you when you had your first kiss? Who? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
What is your favorite position? Why?
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,
44~ Care to share something about yourself that no one else knows about you?
11~ Have you ever been caught by your parents or children or others while having sex?
1- What was your first impression of me? Has it changed?
34~ Do you like the lights on or off during sex?
18- How often do you drink alcohol? What is your favorite drink?
Any that are a turn off?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
* 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)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
12- What’s your favorite food? What’s your least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
*** Random Questions ***
19- Do/have you smoked? What do you prefer? How often?
3- Should Pluto still be considered a planet? 4- How about smoking?
71~ Would you give your partner a hand or foot job? Would you receive one?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
76~ Have you had a threesome? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
21- What's your favorite way to spend a weekend or time off?
11- How about if they like a certain sports team? 12-How about drinking too much?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
What have you learned about me that was new and/or surprising?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
If you win, what will you make them do?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Would you do it again, and would you rather 2 females or 2 males?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
38~ Share your most embarrassing sexual memory?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
6- Do you have dreams? Can you remember them? What do you usually dream about?
The Ice Breaker Questions
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
89~ Do you like taking showers together?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you like the “69” position? Do you prefer to be on top or bottom?
33- Beach or Mountains? Or is there another place to like better?
50~ How many children do you have? What are their ages?
18~ Who/when was your first “crush”?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
92~ Everyone needs a “safe” word. What is yours?
*** Questions About Me ***
45~ How do you feel about me blindfolding you? How about blindfolding me?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
9- What’s your favorite season and why? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
80~ Share your top three fantasies/desires. (Be detailed) 😊
52~ What are your hobbies?
81~ Do you have any kinks and/or fetishes?
*** Questions about Relationships/Past ***
Does the thought excite you? Care to share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Can you Deep Throat? Do you like the taste of yourself?
2- What’s your favorite color? Do you a least favorite?
Do you like it when they show and tell you what they want?
60~ How important is oral sex? Do you like receiving? Do you like giving?
27- What was/ is nickname? Does it have a meaning behind it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Repairman/Lonely Wife Virgin/Experienced
14- What is an embarrassing moment in your life? How about your most embarrassing?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Model/Photographer Police/Criminal
42~ What’s your biggest regret in life?
33- If you could visit any time period, when would you pick? Please explain why?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
51~ Are you willing to play adult games with your partner?
What have you learned about yourself that you did not before this?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would /have you ever given your partner a lap dance and Striptease?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
49~ How many times have you been married? Why did they end?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
9- Is there something you’ve always wanted to ask me but you’re afraid?
39~ What are your love languages?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Get this wrong and this could mean the end… :-) some funny, some not…
29~ What are some things that turn you off? What is your biggest turn off?
12- What is the weirdest thing you've ever eaten?
37- Do you like your name? If you could change it, what would you change it too?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
How about if they talk dirty and/or call you names?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
8- What are your thoughts on politics?
14- What's your favorite dessert? Do you a least favorite?
What would you say to prove to yourself that it was really you?
65~ Describe the best orgasm you’ve ever had? Care to share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
20- What’s your favorite candy? What’s your least favorite?
How many partners have you had oral sex with? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
25~ How do you feel about PDA? (Public Display of Affection)
Master/Slave Boss/Maid
11- What's your favorite restaurant? What’s your least favorite?
7- What are your thoughts on religion? Is there an afterlife?
83~ How do you feel about Porn?
How old are you? Male or Female?
7- What if a person smells a certain way? 8- How about smoking?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Over time has your thoughts on sex changed?
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)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
29- How superstitious are you?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
Do you watch it? What is your favorite?
15~ Have you ever been “in love”? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you ever want to be woken up with oral and/or intercourse?
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?
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?
32- What's your greatest talent? Can I see it right now?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
21~ What was the best date you ever went on? What has been the worst?
What do you dislike about me? I asked you to be 100% honest.
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
52~ Are you willing to make “those types” of bets with your partner?
Family Relation Age Play
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
30~ What's something unexpected that turns you on?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
5- Have you ever been hypnotized? Would you allow yourself to be?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would you read them together?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
36~ What is your favorite time of day to have sex/make love?
I would allow you to do it… What would you do to me?
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?
31- If given a chance to be immortal, would you take it? Why?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
11- List at least 5 things on your bucket list. Have you done any of them already?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
17- What’s your favorite holiday? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you mind if your partner watched it? How about together vs alone?
48~ Do you have any siblings? Are you close to your family?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What was the longest? What was the shortest?
51~ What tends to bring a smile to your face?
Prisoner/Prison Guard Landlord/Tenant
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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)
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…
23- What is your dream job? What was it as a child?
10- List 5 of your top pet peeves.
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…
61~ How willing would you be to try new sexual positions?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
(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 well do you know me? And some of your thoughts about me
92~ Have you ever had or have an STD? How many? What was it?
26~ What side of the bed do you sleep on?
If you say it, I will stop, and we can talk about it when you are ready.
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?
13- How about having a certain hair cut/style?
How many times do you think you have “made love”?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?