What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 01:19
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
47~ What would be your dream job and why?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
How can one learn to talk frankly?
22- What is your favorite childhood memory? What is your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
81~ Do you have any kinks and/or fetishes?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
42~ What’s your biggest regret in life?
Do you have a favorite? Is it ok if your partner does?
Digital Workers Have Arrived in Banking - WSJ
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
33- If you could visit any time period, when would you pick? Please explain why?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Teen TikTok skin care craze may be harmful — and expensive, study finds - CNN
Would you do it again, and would you rather 2 females or 2 males?
53~ How much can you tell me about the one thing you are most passionate about?
Doctor/Nurse Stripper/Client
This Vitamin May Lower Your Stroke Risk by 17%, New Study Says - EatingWell
31- If given a chance to be immortal, would you take it? Why?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
15- What bad habit do you wish you could quit? Do you have any addictions?
How well do you know me? And some of your thoughts about me
14- What is an embarrassing moment in your life? How about your most embarrassing?
11- How about if they like a certain sports team? 12-How about drinking too much?
How many partners have you had oral sex with? Who? Care to Share?
5~ When you first started having sex, was it what you thought it would be?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Why do I smell bad even though I have good hygiene?
If yes, what?
20- What’s your favorite candy? What’s your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How to protect yourself from wildfire smoke and poor air quality - The Washington Post
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
James Hagens’ Islanders homecoming is no longer just a pipe dream - New York Post
What do you dislike about me? I asked you to be 100% honest.
28- What are some things that people do that irritate you?
11~ Have you ever been caught by your parents or children or others while having sex?
How come Trump is so weak in backing down from some tariffs?
37- Do you like your name? If you could change it, what would you change it too?
*** Deal Breaker Questions ***
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Any that are a turn off?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
49~ How many times have you been married? Why did they end?
29~ What are some things that turn you off? What is your biggest turn off?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Get this wrong and this could mean the end… :-) some funny, some not…
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
* Give a rating for each one (0-100)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
18- How often do you drink alcohol? What is your favorite drink?
40~ What’s the weirdest place you’ve ever had sex?
33- Beach or Mountains? Or is there another place to like better?
Do you like it when they show and tell you what they want?
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?
48~ Have you ever paid or been paid for sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
13- What’s your favorite drink? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What have you learned about yourself that you did not before this?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
67~ Do you like it when your partner moans and/or is vocal during sex?
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…
82~ Do you have any fantasies involving Role-Playing?
30~ What's something unexpected that turns you on?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
3- What’s your favorite smell? 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?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Questions about Relationships/Past ***
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, 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,
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
7- What if a person smells a certain way? 8- How about smoking?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
52~ What are your hobbies?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
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?
Escort/Client Job Applicant/Hiring Manager
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”?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
I would allow you to do it… What would you do to me?
Teacher/Student Stranger/One Night Stand
Do you shave/trim your pubic hair? For you guys do you shave your balls?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
89~ Do you like taking showers together?
Would /have you ever given your partner a lap dance and Striptease?
9- What’s your favorite season and why? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What was the longest? What was the shortest?
48~ Do you have any siblings? Are you close to your family?
83~ How do you feel about Porn?
18~ Who/when was your first “crush”?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Would you read them together?
17- What’s your favorite holiday? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
10~ How many dates are necessary before you to have sex with someone?
36~ What is your favorite time of day to have sex/make love?
34~ Do you like the lights on or off during sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Nothing too Serious
7-What do I do in bed that drives you wild? How about, what turns you off?
62~ Have you used adult toys?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
29- How superstitious are you?
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)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
If you win, what will you make them do?
If NO, would you ever have one? Would it be with 2 men or 2 women?
34- Ever been to a concert? What was your favorite? Who would you like to see?
9- Is there something you’ve always wanted to ask me but you’re afraid?
44~ Care to share something about yourself that no one else knows about you?
15~ Have you ever been “in love”? Who? Care to Share?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
22- Do you have any birth marks? How about scars? Care to share how you got them?
13~ Is there a difference between, making love, having sex, and fucking?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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?
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?
61~ How willing would you be to try new sexual positions?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
21~ What was the best date you ever went on? What has been the worst?
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?
What is your view on sex? Meaning, When/Where/ How often/
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Would you mind if your partner watched it? How about together vs alone?
Master/Slave Boss/Maid
6- Do you have dreams? Can you remember them? What do you usually dream about?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
7- What are your thoughts on religion? Is there an afterlife?
92~ Everyone needs a “safe” word. What is yours?
23- What is your dream job? What was it as a child?
51~ Are you willing to play adult games with your partner?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
60~ How important is oral sex? Do you like receiving? Do you like giving?
You know that I will be 100% truthful, so ask.
13- What is the craziest/scariest thing you've ever done?
52~ Are you willing to make “those types” of bets with your partner?
25~ How do you feel about PDA? (Public Display of Affection)
What would you say to prove to yourself that it was really you?
Repairman/Lonely Wife Virgin/Experienced
Over time has your thoughts on sex changed?
Do you like the “69” position? Do you prefer to be on top or bottom?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Nurse/Patient Celebrity/Fan
3- What Superhero or Superpower would you want to be/have?
17- Have you ever done drugs? Which ones? How often?
Any that are a turn off?
*** Questions About Me ***
84~ How do you feel about reading/listening to adult stories?
That one or two things that made you go hmmmm, OMG or wow!
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?
1- What’s your favorite animal? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
65~ Describe the best orgasm you’ve ever had? Care to share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
45~ How do you feel about me blindfolding you? How about blindfolding me?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What have you learned about me that was new and/or surprising?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
38~ Share your most embarrassing sexual memory?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
70~ Would/do you have/like anal sex?
Model/Photographer Police/Criminal
How old are you? Male or Female?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Have you ever? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
How about if they talk dirty and/or call you names?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
4- For a pet, Cat, dog or other?
76~ Have you had a threesome? Care to Share?
*** Random Questions ***
9~ How many times over your lifetime do you think you have had sex so far?
Prisoner/Prison Guard Landlord/Tenant
Would you ever want to be woken up with oral and/or intercourse?
Family Relation Age Play
12- What’s your favorite food? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
39~ What are your love languages?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
21- What's your favorite way to spend a weekend or time off?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
15- What's your favorite saying? What word or phrase is your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
51~ What tends to bring a smile to your face?
9- If you could have three wishes, what would they be? Why?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
The Ice Breaker Questions
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
71~ Would you give your partner a hand or foot job? Would you receive one?
10- List 5 of your top pet peeves.
1~ How old were you when you had your first kiss? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
(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…)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
8- What's your favorite flavor of ice cream? Do you a least favorite?
Do you think this brought you closer together?
Do you watch it? What is your favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What is your favorite position? Why?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
26~ What side of the bed do you sleep on?
1- What was your first impression of me? Has it changed?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Will you cheat again? How can, you be sure? Define what cheating is to you.
If YES, was it with 2 men or 2 women? Did you enjoy it?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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?
14- What's your favorite dessert? 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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Can you Deep Throat? Do you like the taste of yourself?
5- Have you ever been hypnotized? Would you allow yourself to be?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
50~ How many children do you have? What are their ages?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What is your favorite toy? Ever wanted to try a specific toy?
Please share Did you stop?
92~ Have you ever had or have an STD? How many? What was it?
*** What’s Your Favorite…? ***
19- What’s your favorite fairytale? What’s your least favorite?
2- What’s your favorite color? Do you a least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
8- What are your thoughts on politics?
13- How about having a certain hair cut/style?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
19~ Who/when was your first “heartbreak”?