What is the most interesting question you can ask to get to know someone?
Last Updated: 17.06.2025 00:24

Master/Slave Boss/Maid
7- What if a person smells a certain way? 8- How about smoking?
48~ Do you have any siblings? Are you close to your family?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
31- If given a chance to be immortal, would you take it? Why?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Do you have a favorite? Is it ok if your partner does?
Why is it called iOS 26? What happened to iOS 19 for iPhone - 9to5Mac
71~ Would you give your partner a hand or foot job? Would you receive one?
How well do you know me? And some of your thoughts about me
11- How about if they like a certain sports team? 12-How about drinking too much?
What are some of the best relationship advice for men?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Would you read them together?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Would /have you ever given your partner a lap dance and Striptease?
32- What's your greatest talent? Can I see it right now?
Why is dating so frustrating and difficult for a guy?
Any that are a turn off?
53~ How much can you tell me about the one thing you are most passionate about?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What did Chandrashekhar Azad say about Hinduism during a podcast?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
52~ Are you willing to make âthose typesâ of bets with your partner?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What is your review of the Redmi 9A? Is it worth buying?
Please share Did you stop?
12- Whatâs your favorite food? Whatâs your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
How did you as a human being change while growing up?
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?
22- What is your favorite childhood memory? What is your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Exactly When Apple Will Launch iPhone 17 And iPhone 17 Pro - Forbes
Doctor/Nurse Stripper/Client
15- What's your favorite saying? What word or phrase is your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
When does a man tell a woman he has feelings for her?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
38~ Share your most embarrassing sexual memory?
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?
28- What are some things that people do that irritate you?
What is your favorite position? Why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
What is the opposite personality type of someone with ASPD (antisocial personality disorder)?
83~ How do you feel about Porn?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
What are some photos of female sexual organs?
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?
What is your view on sex? Meaning, When/Where/ How often/
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)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
76~ Have you had a threesome? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
62~ Have you used adult toys?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
13~ Is there a difference between, making love, having sex, and fucking?
Can you Deep Throat? Do you like the taste of yourself?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
10- What is your favorite family tradition? Whatâs your least favorite?
1- What was your first impression of me? Has it changed?
Family Relation Age Play
*** Deal Breaker Questions ***
What do you dislike about me? I asked you to be 100% honest.
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
7- What are your thoughts on religion? Is there an afterlife?
26~ What side of the bed do you sleep on?
10~ How many dates are necessary before you to have sex with someone?
15- What bad habit do you wish you could quit? Do you have any addictions?
7-What do I do in bed that drives you wild? How about, what turns you off?
Have you ever? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
11- What's your favorite restaurant? Whatâs your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
25~ How do you feel about PDA? (Public Display of Affection)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with 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?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
49~ How many times have you been married? Why did they end?
2- Whatâs your favorite color? Do you a least favorite?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
13- Whatâs your favorite drink? Whatâs your least favorite?
92~ Everyone needs a âsafeâ word. What is yours?
Nothing too Serious
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
50~ How many children do you have? What are their ages?
1~ How old were you when you had your first kiss? Who? Care to Share?
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 âPASSâ 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 yourselfâŚ
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
21~ What was the best date you ever went on? What has been the worst?
45~ How do you feel about me blindfolding you? How about blindfolding me?
3- What Superhero or Superpower would you want to be/have?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
If you lose, are you willing to be their sex slave for a day, (anything goes)?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Does the thought excite you? Care to share?
92~ Have you ever had or have an STD? How many? What was it?
18- How often do you drink alcohol? What is your favorite drink?
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 togetherâŚ
That one or two things that made you go hmmmm, OMG or wow!
The Ice Breaker Questions
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Over time has your thoughts on sex changed?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Would you allow me to clean every part of your body with my soapy hands and fingers?
17- Have you ever done drugs? Which ones? How often?
89~ Do you like taking showers together?
Do you watch it? What is your favorite?
Do you think this brought you closer together?
40~ Whatâs the weirdest place youâve ever had sex?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
37- Do you like your name? If you could change it, what would you change it too?
36~ What is your favorite time of day to have sex/make love?
* Give a rating for each one (0-100)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
34~ Do you like the lights on or off during sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
Model/Photographer Police/Criminal
14- What's your favorite dessert? Do you a least favorite?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
You know that I will be 100% truthful, so ask.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
*** Questions about Relationships/Past ***
22- Do you have any birth marks? How about scars? Care to share how you got them?
I would allow you to do it⌠What would you do to me?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
51~ Are you willing to play adult games with your partner?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
47~ What would be your dream job and why?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
33- If you could visit any time period, when would you pick? Please explain why?
67~ Do you like it when your partner moans and/or is vocal during sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
28~ What are some things that turn on? What is your biggest turn on?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
9- Whatâs your favorite season and why? Whatâs your least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Do you like the â69â position? Do you prefer to be on top or bottom?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If you win, what will you make them do?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
If you say it, I will stop, and we can talk about it when you are ready.
Would you ever want to be woken up with oral and/or intercourse?
*** Whatâs Your FavoriteâŚ? ***
44~ Care to share something about yourself that no one else knows about you?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What have you learned about yourself that you did not before this?
82~ Do you have any fantasies involving Role-Playing?
8- What are your thoughts on politics?
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?
11~ Have you ever been caught by your parents or children or others while having sex?
Would you do it again, and would you rather 2 females or 2 males?
51~ What tends to bring a smile to your face?
36- Do you play video games? What is your favorite? Do you a least favorite?
What have you learned about me that was new and/or surprising?
33- Beach or Mountains? Or is there another place to like better?
70~ Would/do you have/like anal sex?
Would you mind if your partner watched it? How about together vs alone?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
19- Do/have you smoked? What do you prefer? How often?
61~ How willing would you be to try new sexual positions?
5~ When you first started having sex, was it what you thought it would be?
29~ What are some things that turn you off? What is your biggest turn off?
If NO, would you ever have one? Would it be with 2 men or 2 women?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Escort/Client Job Applicant/Hiring Manager
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Any that are a turn off?
9- Is there something youâve always wanted to ask me but youâre afraid?
13- How about having a certain hair cut/style?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Questions About Me ***
Teacher/Student Stranger/One Night Stand
Do you like it when they show and tell you what they want?
11- List at least 5 things on your bucket list. Have you done any of them already?
How many times do you think you have âmade loveâ?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
23- What is your dream job? What was it as a child?
Nurse/Patient Celebrity/Fan
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
80~ Share your top three fantasies/desires. (Be detailed) đ
19- Whatâs your favorite fairytale? Whatâs your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
18~ Who/when was your first âcrushâ?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How old are you? Male or Female?
12- What is the weirdest thing you've ever eaten?
30~ What's something unexpected that turns you on?
Prisoner/Prison Guard Landlord/Tenant
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŚ)
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
What was the longest? What was the shortest?
How many partners have you had oral sex with? Who? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Repairman/Lonely Wife Virgin/Experienced
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
What is your favorite toy? Ever wanted to try a specific toy?
34- Ever been to a concert? What was your favorite? Who would you like to see?
20- Whatâs your favorite candy? Whatâs your least favorite?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
84~ How do you feel about reading/listening to adult stories?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
65~ Describe the best orgasm youâve ever had? Care to share?
42~ Whatâs your biggest regret in life?
5- Have you ever been hypnotized? Would you allow yourself to be?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
4- For a pet, Cat, dog or other?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
81~ Do you have any kinks and/or fetishes?
6- Do you have dreams? Can you remember them? What do you usually dream about?
27- What was/ is nickname? Does it have a meaning behind it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
52~ What are your hobbies?
9- If you could have three wishes, what would they be? Why?
39~ What are your love languages?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
48~ Have you ever paid or been paid for sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
15~ Have you ever been âin loveâ? Who? Care to Share?
19~ Who/when was your first âheartbreakâ?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What would you say to prove to yourself that it was really you?
21- What's your favorite way to spend a weekend or time off?
How about if they talk dirty and/or call you names?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
If yes, what?
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
1- Whatâs your favorite animal? Do you a least favorite?
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
*** Random Questions ***
29- How superstitious are you?
3- What was the most surprising thing youâve learned about me throughout our relationship?
60~ How important is oral sex? Do you like receiving? Do you like giving?
10- List 5 of your top pet peeves.
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?
17- Whatâs your favorite holiday? Whatâs your least favorite?
3- Whatâs your favorite smell? Do you a least favorite?