What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 00:11
Can you Deep Throat? Do you like the taste of yourself?
Model/Photographer Police/Criminal
42~ What’s your biggest regret in life?
What is your review of the Redmi 9A? Is it worth buying?
Would /have you ever given your partner a lap dance and Striptease?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
1~ How old were you when you had your first kiss? Who? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
84~ How do you feel about reading/listening to adult stories?
15- What bad habit do you wish you could quit? Do you have any addictions?
34~ Do you like the lights on or off during sex?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
14- What is an embarrassing moment in your life? How about your most embarrassing?
If gays can get married, why can't I marry my dog or a cheeseburger?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Teacher/Student Stranger/One Night Stand
12- What is the weirdest thing you've ever eaten?
Analysts revamp forecast for Nvidia-backed AI stock - TheStreet
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
13- What’s your favorite drink? What’s your least favorite?
Thanks to FIFA, Atlanta’s first-ever Club World Cup game was underwhelming - AJC.com
49~ If you could, would you want to be the opposite sex for a day, week, or year?
71~ Would you give your partner a hand or foot job? Would you receive one?
What do you dislike about me? I asked you to be 100% honest.
What is the worst name in Tolkien’s legendarium (meaning and look)?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What have you learned about me that was new and/or surprising?
11~ Have you ever been caught by your parents or children or others while having sex?
Where did Noah build the Ark? Was it in a desert or near water?
If you say it, I will stop, and we can talk about it when you are ready.
30~ What's something unexpected that turns you on?
13- What is the craziest/scariest thing you've ever done?
watchOS 26 Moves Latest Apple Watch Models to New Architecture - MacRumors
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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
37- Do you like your name? If you could change it, what would you change it too?
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 music in the background or silence? Is there a sexy song that tends to get you in the mood?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What are the common formulas for improvising ornaments in bel canto singing?
How old are you? Male or Female?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Joey Chestnut, barred last July, returns to Nathan’s hot dog eating contest - The Washington Post
32- What's your greatest talent? Can I see it right now?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Have you ever? 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…)
*** Questions about Relationships/Past ***
51~ What tends to bring a smile to your face?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
3- Should Pluto still be considered a planet? 4- How about smoking?
61~ How willing would you be to try new sexual positions?
50~ How many children do you have? What are their ages?
28- What are some things that people do that irritate you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
The Ice Breaker Questions
64~ When was your very first orgasm? When was your first from having sex? Care to share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Does the thought excite you? Care to share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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- Do you have dreams? Can you remember them? What do you usually dream about?
48~ Do you have any siblings? Are you close to your family?
27- What was/ is nickname? Does it have a meaning behind it?
23- What is your dream job? What was it as a child?
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
5~ When you first started having sex, was it what you thought it would be?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
Nurse/Patient Celebrity/Fan
81~ Do you have any kinks and/or fetishes?
83~ How do you feel about Porn?
Do you like it when they show and tell you what they want?
How many partners have you had oral sex with? Who? Care to Share?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
18- How often do you drink alcohol? What is your favorite drink?
29~ What are some things that turn you off? What is your biggest turn off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What is your favorite position? Why?
How many times do you think you have “made love”?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
What have you learned about yourself that you did not before this?
51~ Are you willing to play adult games with your partner?
67~ Do you like it when your partner moans and/or is vocal during sex?
What was the longest? What was the shortest?
Master/Slave Boss/Maid
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
7-What do I do in bed that drives you wild? How about, what turns you off?
*** Questions About Me ***
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
21- What's your favorite way to spend a weekend or time off?
Any that are a turn off?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
70~ Would/do you have/like anal sex?
15- What's your favorite saying? What word or phrase is your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
*** What’s Your Favorite…? ***
36- Do you play video games? What is your favorite? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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…
4- For a pet, Cat, dog or other?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
13- How about having a certain hair cut/style?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would you mind if your partner watched it? How about together vs alone?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Would you read them together?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
33- Beach or Mountains? Or is there another place to like better?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
17- What’s your favorite holiday? What’s your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
89~ Do you like taking showers together?
Doctor/Nurse Stripper/Client
44~ Care to share something about yourself that no one else knows about you?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
52~ Are you willing to make “those types” of bets with your partner?
Would you ever want to be woken up with oral and/or intercourse?
52~ What are your hobbies?
If you win, what will you make them do?
10~ How many dates are necessary before you to have sex with someone?
48~ Have you ever paid or been paid for sex?
3- What Superhero or Superpower would you want to be/have?
10- List 5 of your top pet peeves.
3- What’s your favorite smell? Do you a least favorite?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
53~ How much can you tell me about the one thing you are most passionate about?
39~ What are your love languages?
34- Ever been to a concert? What was your favorite? Who would you like to see?
92~ Have you ever had or have an STD? How many? What was it?
Any that are a turn off?
Do you watch it? What is your favorite?
2- What’s your favorite color? Do you a least favorite?
Family Relation Age Play
26~ What side of the bed do you sleep on?
9- What’s your favorite season and why? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
12- What’s your favorite food? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
10- What is your favorite family tradition? What’s your least favorite?
What would you say to prove to yourself that it was really you?
82~ Do you have any fantasies involving Role-Playing?
* Give a rating for each one (0-100)
What is your favorite toy? Ever wanted to try a specific toy?
80~ Share your top three fantasies/desires. (Be detailed) 😊
If YES, was it with 2 men or 2 women? Did you enjoy it?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Over time has your thoughts on sex changed?
Do you have a favorite? Is it ok if your partner does?
8- What are your thoughts on politics?
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?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
1- What’s your favorite animal? Do you a least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
14- What's your favorite dessert? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
9- If you could have three wishes, what would they be? Why?
38~ Share your most embarrassing sexual memory?
19- Do/have you smoked? What do you prefer? How often?
33- If you could visit any time period, when would you pick? Please explain why?
18~ Who/when was your first “crush”?
19~ Who/when was your first “heartbreak”?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
62~ Have you used adult toys?
Would you do it again, and would you rather 2 females or 2 males?
How well do you know me? And some of your thoughts about me
8- What's your favorite flavor of ice cream? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
Please share Did you stop?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
How about if they talk dirty and/or call you names?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
21~ What was the best date you ever went on? What has been the worst?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
25~ How do you feel about PDA? (Public Display of Affection)
11- What's your favorite restaurant? What’s your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
Do you think this brought you closer together?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
92~ Everyone needs a “safe” word. What is yours?
28~ What are some things that turn on? What is your biggest turn on?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
*** Random Questions ***
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Escort/Client Job Applicant/Hiring Manager
60~ How important is oral sex? Do you like receiving? Do you like giving?
17- Have you ever done drugs? Which ones? How often?
15~ Have you ever been “in love”? Who? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
Prisoner/Prison Guard Landlord/Tenant
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
47~ What would be your dream job and why?
Nothing too Serious
11- How about if they like a certain sports team? 12-How about drinking too much?
That one or two things that made you go hmmmm, OMG or wow!
49~ How many times have you been married? Why did they end?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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~ Is there a difference between, making love, having sex, and fucking?
I would allow you to do it… What would you do to me?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
29- How superstitious are you?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
*** Deal Breaker Questions ***
22- What is your favorite childhood memory? What is your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
7- What are your thoughts on religion? Is there an afterlife?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
31- If given a chance to be immortal, would you take it? Why?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
76~ Have you had a threesome? Care to Share?
1- What was your first impression of me? Has it changed?
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?
36~ What is your favorite time of day to have sex/make love?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If yes, what?
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…
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Get this wrong and this could mean the end… :-) some funny, some not…
Do you like the “69” position? Do you prefer to be on top or bottom?
You know that I will be 100% truthful, so ask.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)