What is the most interesting question you can ask to get to know someone?
Last Updated: 23.06.2025 01:39
3- What Superhero or Superpower would you want to be/have?
Can you Deep Throat? Do you like the taste of yourself?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
How many partners have you had oral sex with? Who? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Where did cosmic rays come from? Astrophysicists are closer to finding out - Phys.org
If yes, what?
Model/Photographer Police/Criminal
21~ What was the best date you ever went on? What has been the worst?
The two rules investors need to follow right now as the S&P 500 eyes a return to 6,000 - MarketWatch
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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....)
Weight loss connected to nerve cells in the brain, study finds - The Brighter Side of News
28- What are some things that people do that irritate you?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Would you read them together?
Meta Agreed to Pay up for Scale AI but Then Wanted More for Its Money - The Information
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
10~ How many dates are necessary before you to have sex with someone?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
How do you leave a relationship when you are still in love?
22- What is your favorite childhood memory? What is your least favorite?
13- How about having a certain hair cut/style?
92~ Everyone needs a “safe” word. What is yours?
James Webb Space Telescope unveils fiery origins of a distant, hellish exoplanet - Space
20- What’s your favorite candy? What’s your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would /have you ever given your partner a lap dance and Striptease?
Fear of Uncertainty Held S&P 500 Back From Record. Now It’s Real - Bloomberg.com
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
45~ How do you feel about me blindfolding you? How about blindfolding me?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Outer Worlds 2 Is Xbox's First $80 Video Game - Kotaku
You know that I will be 100% truthful, so ask.
Repairman/Lonely Wife Virgin/Experienced
3- What was the most surprising thing you’ve learned about me throughout our relationship?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What is your favorite toy? Ever wanted to try a specific toy?
Any that are a turn off?
What have you learned about yourself that you did not before this?
7- What are your thoughts on religion? Is there an afterlife?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Is there a specific time frame for therapists to tell their clients they are wrong?
62~ Have you used adult toys?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Why is it difficult to get a job?
51~ Are you willing to play adult games with your partner?
17- What’s your favorite holiday? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What are your main K-pop groups? (Or groups you listen to)?
26~ What side of the bed do you sleep on?
29~ What are some things that turn you off? What is your biggest turn off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Does the thought excite you? 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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
29- How superstitious are you?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
*** Random Questions ***
13- What is the craziest/scariest thing you've ever done?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What was the longest? What was the shortest?
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
3- What’s your favorite smell? Do you a least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How about if they talk dirty and/or call you names?
14- What's your favorite dessert? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
If you win, what will you make them do?
17- Have you ever done drugs? Which ones? How often?
40~ What’s the weirdest place you’ve ever had sex?
7~ How many times in one day have you had sex? Who/When/Where? 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 “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…
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,
47~ What would be your dream job and why?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
Have you ever? Care to Share?
48~ Have you ever paid or been paid for sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Get this wrong and this could mean the end… :-) some funny, some not…
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
2- What’s your favorite color? Do you a least favorite?
1- What was your first impression of me? Has it changed?
Please share Did you stop?
* Give a rating for each one (0-100)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Nurse/Patient Celebrity/Fan
5- Have you ever been hypnotized? Would you allow yourself to be?
Over time has your thoughts on sex changed?
*** Questions about Relationships/Past ***
24~ What are your expectations in a relationship? (I know a very big question, take your time)
The Ice Breaker Questions
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Nothing too Serious
What is your view on sex? Meaning, When/Where/ How often/
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
7- What if a person smells a certain way? 8- How about smoking?
Teacher/Student Stranger/One Night Stand
81~ Do you have any kinks and/or fetishes?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
Will you cheat again? How can, you be sure? Define what cheating is to you.
13~ Is there a difference between, making love, having sex, and fucking?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
38~ Share your most embarrassing sexual memory?
25~ How do you feel about PDA? (Public Display of Affection)
4- For a pet, Cat, dog or other?
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your favorite animal? Do you a least favorite?
30~ What's something unexpected that turns you on?
34~ Do you like the lights on or off during sex?
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
70~ Would/do you have/like anal sex?
That one or two things that made you go hmmmm, OMG or wow!
60~ How important is oral sex? Do you like receiving? Do you like giving?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
64~ When was your very first orgasm? When was your first from having sex? 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)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What would you say to prove to yourself that it was really you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7-What do I do in bed that drives you wild? How about, what turns you off?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
27- What was/ is nickname? Does it have a meaning behind it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
82~ Do you have any fantasies involving Role-Playing?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Escort/Client Job Applicant/Hiring Manager
What do you dislike about me? I asked you to be 100% honest.
52~ What are your hobbies?
8- What are your thoughts on politics?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
18- How often do you drink alcohol? What is your favorite drink?
12- What is the weirdest thing you've ever eaten?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
11- What's your favorite restaurant? What’s your least favorite?
What have you learned about me that was new and/or surprising?
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?
Would you ever want to be woken up with oral and/or intercourse?
19~ Who/when was your first “heartbreak”?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
67~ Do you like it when your partner moans and/or is vocal during sex?
15- What's your favorite saying? What word or phrase is your least favorite?
44~ Care to share something about yourself that no one else knows about you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
11- List at least 5 things on your bucket list. Have you done any of them already?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
48~ Do you have any siblings? Are you close to your family?
22- Do you have any birth marks? How about scars? Care to share how you got them?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
3- Should Pluto still be considered a planet? 4- How about smoking?
39~ What are your love languages?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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…
15~ Have you ever been “in love”? Who? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
71~ Would you give your partner a hand or foot job? Would you receive one?
*** What’s Your Favorite…? ***
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Master/Slave Boss/Maid
How many times do you think you have “made love”?
76~ Have you had a threesome? Care to Share?
Do you think this brought you closer together?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How well do you know me? And some of your thoughts about me
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
If you say it, I will stop, and we can talk about it when you are ready.
28~ What are some things that turn on? What is your biggest turn on?
18~ Who/when was your first “crush”?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you do it again, and would you rather 2 females or 2 males?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** Deal Breaker Questions ***
80~ Share your top three fantasies/desires. (Be detailed) 😊
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
34- Ever been to a concert? What was your favorite? Who would you like to see?
19- What’s your favorite fairytale? What’s your least favorite?
89~ Do you like taking showers together?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
9- If you could have three wishes, what would they be? Why?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
50~ How many children do you have? What are their ages?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Doctor/Nurse Stripper/Client
46~ Have you ever used furniture, or other types of things to aid you while having sex?
I would allow you to do it… What would you do to me?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you like it when they show and tell you what they want?
49~ How many times have you been married? Why did they end?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
11~ Have you ever been caught by your parents or children or others while having sex?
37- Do you like your name? If you could change it, what would you change it too?
Prisoner/Prison Guard Landlord/Tenant
36~ What is your favorite time of day to have sex/make love?
51~ What tends to bring a smile to your face?
12- What’s your favorite food? What’s your least favorite?
(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…)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
10- List 5 of your top pet peeves.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
84~ How do you feel about reading/listening to adult stories?
33- Beach or Mountains? Or is there another place to like better?
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?
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?
13- What’s your favorite drink? What’s your least favorite?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
1~ How old were you when you had your first kiss? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Family Relation Age Play
19- Do/have you smoked? What do you prefer? How often?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
61~ How willing would you be to try new sexual positions?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
5~ When you first started having sex, was it what you thought it would be?
How old are you? Male or Female?
23- What is your dream job? What was it as a child?
8- What's your favorite flavor of ice cream? Do you a least favorite?
42~ What’s your biggest regret in life?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
52~ Are you willing to make “those types” of bets with your partner?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Do you have a favorite? Is it ok if your partner does?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
11- How about if they like a certain sports team? 12-How about drinking too much?
83~ How do you feel about Porn?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Any that are a turn off?
35- Do you like playing board or cards game? 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 mind if your partner watched it? How about together vs alone?
What is your favorite position? Why?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
*** Questions About Me ***
32- What's your greatest talent? Can I see it right now?
53~ How much can you tell me about the one thing you are most passionate about?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
21- What's your favorite way to spend a weekend or time off?
Do you like the “69” position? Do you prefer to be on top or bottom?
18- What’s your favorite way to relax after a long day? What’s your least favorite?