What is the most interesting question you can ask to get to know someone?
09.06.2025 00:02
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
84~ How do you feel about reading/listening to adult stories?
Can you Deep Throat? Do you like the taste of yourself?
Can people who have never met you tell if you are a covert narcissist?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Teacher/Student Stranger/One Night Stand
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Why do foolish atheists think their strange delusional theories are facts?
71~ Would you give your partner a hand or foot job? Would you receive one?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How do I express sarcasm in non-dialogue text when writing a fiction novel?
Prisoner/Prison Guard Landlord/Tenant
Over time has your thoughts on sex changed?
50~ How many children do you have? What are their ages?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
The "Tooth Hurty" Joke Has Its Origins In Ancient, Armored Fish - Defector
28~ What are some things that turn on? What is your biggest turn on?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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)
NYC’s Noisy Skies Get Electric With Beta’s Demo Flight Into JFK - Bloomberg.com
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?
Nurse/Patient Celebrity/Fan
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
I would allow you to do it… What would you do to me?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
How about if they talk dirty and/or call you names?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What is the cost of implementing synchronized traffic lights in a mid-sized city?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What is it like to have an insanely beautiful girlfriend?
65~ Describe the best orgasm you’ve ever had? Care to share?
35- Do you like playing board or cards game? What is your favorite? 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?
Apple issues urgent warning to all 1.8 billion iPhone users - ladbible.com
Will you cheat again? How can, you be sure? Define what cheating is to you.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
6- Do you have dreams? Can you remember them? What do you usually dream about?
What did Chandrashekhar Azad say about Hinduism during a podcast?
Please share Did you stop?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
5~ When you first started having sex, was it what you thought it would be?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
13- What is the craziest/scariest thing you've ever done?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
What is your view on sex? Meaning, When/Where/ How often/
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
76~ Have you had a threesome? Care to Share?
Any that are a turn off?
89~ Do you like taking showers together?
9~ How many times over your lifetime do you think you have had sex so far?
21- What's your favorite way to spend a weekend or time off?
What have you learned about me that was new and/or surprising?
22- Do you have any birth marks? How about scars? Care to share how you got them?
What was the longest? What was the shortest?
21~ What was the best date you ever went on? What has been the worst?
18~ Who/when was your first “crush”?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
25~ How do you feel about PDA? (Public Display of Affection)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
51~ What tends to bring a smile to your face?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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,
Repairman/Lonely Wife Virgin/Experienced
12- What’s your favorite food? What’s your least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
38~ Share your most embarrassing sexual memory?
47~ What would be your dream job and why?
4- For a pet, Cat, dog or other?
67~ Do you like it when your partner moans and/or is vocal during sex?
Get this wrong and this could mean the end… :-) some funny, some not…
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
81~ Do you have any kinks and/or fetishes?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
3- What’s your favorite smell? Do you a least favorite?
8- What are your thoughts on politics?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Does the thought excite you? Care to share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
1~ How old were you when you had your first kiss? Who? 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?
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?
Escort/Client Job Applicant/Hiring Manager
What is your favorite position? Why?
9- If you could have three wishes, what would they be? Why?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
19~ Who/when was your first “heartbreak”?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
10~ How many dates are necessary before you to have sex with someone?
Nothing too Serious
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
28- What are some things that people do that irritate you?
Do you like the “69” position? Do you prefer to be on top or bottom?
20- What’s your favorite candy? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
80~ Share your top three fantasies/desires. (Be detailed) 😊
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
19- Do/have you smoked? What do you prefer? How often?
42~ What’s your biggest regret in life?
Would you ever want to be woken up with oral and/or intercourse?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
61~ How willing would you be to try new sexual positions?
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?
10- List 5 of your top pet peeves.
11- How about if they like a certain sports team? 12-How about drinking too much?
32- What's your greatest talent? Can I see it right now?
29- How superstitious are you?
1- What was your first impression of me? Has it changed?
Any that are a turn off?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
48~ Have you ever paid or been paid for sex?
15~ Have you ever been “in love”? Who? Care to Share?
83~ How do you feel about Porn?
Would you read them together?
Do you have a favorite? Is it ok if your partner does?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
30~ What's something unexpected that turns you on?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
*** Deal Breaker Questions ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
51~ Are you willing to play adult games with your partner?
Master/Slave Boss/Maid
52~ What are your hobbies?
19- What’s your favorite fairytale? What’s your least favorite?
Family Relation Age Play
* Give a rating for each one (0-100)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
62~ Have you used adult toys?
8- What's your favorite flavor of ice cream? Do you a least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
Do you like it when they show and tell you what they want?
How old are you? Male or Female?
29~ What are some things that turn you off? What is your biggest turn off?
2- What’s your favorite color? Do you a least favorite?
The Ice Breaker Questions
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
33- Beach or Mountains? Or is there another place to like better?
23- What is your dream job? What was it as a child?
14- What's your favorite dessert? Do you a least favorite?
82~ Do you have any fantasies involving Role-Playing?
49~ How many times have you been married? Why did they end?
Do you think this brought you closer together?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
13~ Is there a difference between, making love, having sex, and fucking?
Doctor/Nurse Stripper/Client
36- Do you play video games? What is your favorite? Do you a least favorite?
34~ Do you like the lights on or off during sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
70~ Would/do you have/like anal sex?
What would you say to prove to yourself that it was really 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.
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
92~ Everyone needs a “safe” word. What is yours?
Model/Photographer Police/Criminal
(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…)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
31- If given a chance to be immortal, would you take it? Why?
36~ What is your favorite time of day to have sex/make love?
5- Have you ever been hypnotized? Would you allow yourself to be?
If you say it, I will stop, and we can talk about it when you are ready.
*** Questions about Relationships/Past ***
11~ Have you ever been caught by your parents or children or others while having sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
60~ How important is oral sex? Do you like receiving? Do you like giving?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What do you dislike about me? I asked you to be 100% honest.
53~ How much can you tell me about the one thing you are most passionate about?
15- What bad habit do you wish you could quit? Do you have any addictions?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
*** Random Questions ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
40~ What’s the weirdest place you’ve ever had sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
If yes, what?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
What is your favorite toy? Ever wanted to try a specific toy?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
11- List at least 5 things on your bucket list. Have you done any of them already?
39~ What are your love languages?
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?
13- What’s your favorite drink? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- Should Pluto still be considered a planet? 4- How about smoking?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
52~ Are you willing to make “those types” of bets with your partner?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
10- What is your favorite family tradition? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
27- What was/ is nickname? Does it have a meaning behind it?
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…
How many times do you think you have “made love”?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
7- What are your thoughts on religion? Is there an afterlife?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
1- What’s your favorite animal? Do you a least favorite?
13- How about having a certain hair cut/style?
18- How often do you drink alcohol? What is your favorite drink?
*** What’s Your Favorite…? ***
Would you allow me to clean every part of your body with my soapy hands and fingers?
Would /have you ever given your partner a lap dance and Striptease?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
45~ How do you feel about me blindfolding you? How about blindfolding me?
*** Questions About Me ***
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
37~ What is the biggest age gap between you and one of your sexual partners? 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 “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…
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
Would you do it again, and would you rather 2 females or 2 males?
You know that I will be 100% truthful, so ask.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
22- What is your favorite childhood memory? What is your least favorite?
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?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
Do you watch it? What is your favorite?
If you win, what will you make them do?
What have you learned about yourself that you did not before this?
12- What is the weirdest thing you've ever eaten?
Have you ever? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
26~ What side of the bed do you sleep on?
11- What's your favorite restaurant? What’s your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
How many partners have you had oral sex with? Who? Care to Share?
How well do you know me? And some of your thoughts about me
37- Do you like your name? If you could change it, what would you change it too?
34- Ever been to a concert? What was your favorite? Who would you like to see?
44~ Care to share something about yourself that no one else knows about you?
92~ Have you ever had or have an STD? How many? What was it?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
That one or two things that made you go hmmmm, OMG or wow!
7-What do I do in bed that drives you wild? How about, what turns you off?
3- What Superhero or Superpower would you want to be/have?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
15- What's your favorite saying? What word or phrase is your least favorite?
17- Have you ever done drugs? Which ones? How often?
21- Do you have any piercings? 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)
Will you kiss after your partner has gone down on you? Swallow or spit semen?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?