What is the most interesting question you can ask to get to know someone?
Last Updated: 25.06.2025 01:53
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Why do liberals refuse to define what a woman is and what does that mean for the future of feminism?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Doctor/Nurse Stripper/Client
Can AI render anti-virus software obsolete and unnecessary?
48~ Have you ever paid or been paid for sex?
Over time has your thoughts on sex changed?
Family Relation Age Play
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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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
17- Have you ever done drugs? Which ones? How often?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
92~ Have you ever had or have an STD? How many? What was it?
21~ What was the best date you ever went on? What has been the worst?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Do you have a favorite? Is it ok if your partner does?
48~ Do you have any siblings? Are you close to your family?
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Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
29~ What are some things that turn you off? What is your biggest turn off?
Any that are a turn off?
13- What’s your favorite drink? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
Crunch time—we’ll soon find out if Amazon’s launch providers are up to the job - Ars Technica
If you win, what will you make them do?
7- What if a person smells a certain way? 8- How about smoking?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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Do you watch it? What is your favorite?
Please share Did you stop?
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…
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11- List at least 5 things on your bucket list. Have you done any of them already?
83~ How do you feel about Porn?
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,
61~ How willing would you be to try new sexual positions?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
69~ Are you willing to have sex while you or your partner is on their period? How about oral 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?
53~ How much can you tell me about the one thing you are most passionate about?
32- What's your greatest talent? Can I see it right now?
13- How about having a certain hair cut/style?
15~ Have you ever been “in love”? Who? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
*** Random Questions ***
Master/Slave Boss/Maid
28- What are some things that people do that irritate you?
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…
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
8- What are your thoughts on politics?
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?
How many partners have you had oral sex with? Who? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
What would you say to prove to yourself that it was really you?
52~ What are your hobbies?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
4- For a pet, Cat, dog or other?
44~ Care to share something about yourself that no one else knows about you?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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~ Is there a difference between, making love, having sex, and fucking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
What have you learned about yourself that you did not before this?
What is your favorite position? Why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Prisoner/Prison Guard Landlord/Tenant
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
84~ How do you feel about reading/listening to adult stories?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
67~ Do you like it when your partner moans and/or is vocal during sex?
*** What’s Your Favorite…? ***
*** Deal Breaker Questions ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
9~ How many times over your lifetime do you think you have had sex so far?
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)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
10~ How many dates are necessary before you to have sex with someone?
18- How often do you drink alcohol? What is your favorite drink?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
49~ How many times have you been married? Why did they end?
39~ What are your love languages?
If NO, would you ever have one? Would it be with 2 men or 2 women?
50~ How many children do you have? What are their ages?
22- What is your favorite childhood memory? What is your least favorite?
82~ Do you have any fantasies involving Role-Playing?
How many times do you think you have “made love”?
(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…)
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Model/Photographer Police/Criminal
3- Should Pluto still be considered a planet? 4- How about smoking?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
89~ Do you like taking showers together?
That one or two things that made you go hmmmm, OMG or wow!
If yes, what?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
1~ How old were you when you had your first kiss? Who? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
*** Questions About Me ***
What is your favorite toy? Ever wanted to try a specific toy?
Get this wrong and this could mean the end… :-) some funny, some not…
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
3- What Superhero or Superpower would you want to be/have?
19~ Who/when was your first “heartbreak”?
15- What's your favorite saying? What word or phrase is your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
76~ Have you had a threesome? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
If you say it, I will stop, and we can talk about it when you are ready.
Nothing too Serious
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?
20- What’s your favorite candy? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
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?
13- What is the craziest/scariest thing you've ever done?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
5~ When you first started having sex, was it what you thought it would be?
15- What bad habit do you wish you could quit? Do you have any addictions?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
9- What’s your favorite season and why? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Would you ever want to be woken up with oral and/or intercourse?
36~ What is your favorite time of day to have sex/make love?
Would /have you ever given your partner a lap dance and Striptease?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Would you read them together?
33- Beach or Mountains? Or is there another place to like better?
51~ Are you willing to play adult games with your partner?
5- Have you ever been hypnotized? Would you allow yourself to be?
30~ What's something unexpected that turns you on?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
What have you learned about me that was new and/or surprising?
7-What do I do in bed that drives you wild? How about, what turns you off?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
Do you like it when they show and tell you what they want?
10- List 5 of your top pet peeves.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
51~ What tends to bring a smile to your face?
70~ Would/do you have/like anal sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
26~ What side of the bed do you sleep on?
23- What is your dream job? What was it as a child?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
The Ice Breaker Questions
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
1- What was your first impression of me? Has it changed?
62~ Have you used adult toys?
12- What’s your favorite food? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
34- Ever been to a concert? What was your favorite? Who would you like to see?
81~ Do you have any kinks and/or fetishes?
80~ Share your top three fantasies/desires. (Be detailed) 😊
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
29- How superstitious are you?
Does the thought excite you? Care to share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
19- What’s your favorite fairytale? What’s your least favorite?
*** Questions about Relationships/Past ***
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
9- If you could have three wishes, what would they be? Why?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
42~ What’s your biggest regret in life?
38~ Share your most embarrassing sexual memory?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
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?
21- What's your favorite way to spend a weekend or time off?
If YES, was it with 2 men or 2 women? Did you enjoy it?
11- How about if they like a certain sports team? 12-How about drinking too much?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7- What are your thoughts on religion? Is there an afterlife?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
17- What’s your favorite holiday? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
12- What is the weirdest thing you've ever eaten?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
What do you dislike about me? I asked you to be 100% honest.
14- What's your favorite dessert? Do you a least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What was the longest? What was the shortest?
How old are you? Male or Female?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Have you ever? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
47~ What would be your dream job and why?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Do you think this brought you closer together?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
3- What’s your favorite smell? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
2- What’s your favorite color? Do you a 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?
10- What is your favorite family tradition? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
11- What's your favorite restaurant? What’s your least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
28~ What are some things that turn on? What is your biggest turn on?
92~ Everyone needs a “safe” word. What is yours?
65~ Describe the best orgasm you’ve ever had? Care to share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Escort/Client Job Applicant/Hiring Manager
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
52~ Are you willing to make “those types” of bets with your partner?
You know that I will be 100% truthful, so ask.
33- If you could visit any time period, when would you pick? Please explain why?
Nurse/Patient Celebrity/Fan
22~ What is the best pickup line anyone has ever used on you? What was the worst?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
11~ Have you ever been caught by your parents or children or others while having sex?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
18~ Who/when was your first “crush”?
How about if they talk dirty and/or call you names?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
36- Do you play video games? What is your favorite? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Teacher/Student Stranger/One Night Stand
34~ Do you like the lights on or off during sex?
25~ How do you feel about PDA? (Public Display of Affection)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
* Give a rating for each one (0-100)
Any that are a turn off?
1- What’s your favorite animal? Do you a least favorite?
I would allow you to do it… What would you do to me?