What is the most interesting question you can ask to get to know someone?
12.06.2025 05:43
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do Flat Earthers exist today? If so, where do they live?
21- What's your favorite way to spend a weekend or time off?
9- If you could have three wishes, what would they be? Why?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Doctor/Nurse Stripper/Client
*** What’s Your Favorite…? ***
Model/Photographer Police/Criminal
89~ Do you like taking showers together?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
48~ Have you ever paid or been paid for sex?
Isn't it a turn on to have sex with a girl in a skirt or in a tight spandex?
Would you read them together?
3- What’s your favorite smell? Do you a 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?
Are landlords allowed to make unreasonable requests?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
7- What are your thoughts on religion? Is there an afterlife?
If you win, what will you make them do?
Oil rallies as Russia-Ukraine tensions offset OPEC+ output hike - Investing.com
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Don’t Try Flying With Erewhon Sunflower Seeds - The Cut
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
A New Law of Nature Attempts to Explain the Complexity of the Universe - WIRED
37- Do you like your name? If you could change it, what would you change it too?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Why do many women wear sleeveless shirts, more so than men?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
51~ What tends to bring a smile to your face?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
It seems that I am cursed with bad luck. How do I break such a curse?
8- What's your favorite flavor of ice cream? Do you a least favorite?
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?
Why do creationists ask for proof of evolution and then ignore the answers?
5~ When you first started having sex, was it what you thought it would be?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
70~ Would/do you have/like anal sex?
The Opener: Teel, Cubs, Tigers, Langeliers - MLB Trade Rumors
What’s the longest time you gone without having sex, after, having it? How much time between the others?
34~ Do you like the lights on or off during sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
Infrared contact lens enables humans to see in dark - DW
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
27- What was/ is nickname? Does it have a meaning behind it?
How old are you? Male or Female?
Why do some films seem to date/age so badly?
81~ Do you have any kinks and/or fetishes?
Do you like it when they show and tell you what they want?
13- What’s your favorite drink? What’s your least favorite?
5 Things to Know Before the Stock Market Opens - Yahoo Finance
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
42~ What’s your biggest regret in life?
22- What is your favorite childhood memory? What is your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Master/Slave Boss/Maid
33- Beach or Mountains? Or is there another place to like better?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
2- What’s your favorite color? Do you a least favorite?
1- What’s your favorite animal? Do you a least favorite?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
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…
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What do you dislike about me? I asked you to be 100% honest.
13- How about having a certain hair cut/style?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
51~ Are you willing to play adult games with your partner?
47~ What would be your dream job and why?
11~ Have you ever been caught by your parents or children or others while having sex?
52~ What are your hobbies?
53~ How much can you tell me about the one thing you are most passionate about?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
25~ How do you feel about PDA? (Public Display of Affection)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
*** Deal Breaker Questions ***
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
8- What are your thoughts on politics?
7- What if a person smells a certain way? 8- How about smoking?
12- What’s your favorite food? What’s your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
7-What do I do in bed that drives you wild? How about, what turns you off?
11- List at least 5 things on your bucket list. Have you done any of them already?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
15- What bad habit do you wish you could quit? Do you have any addictions?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
13~ Is there a difference between, making love, having sex, and fucking?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
20- What’s your favorite candy? What’s your least favorite?
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?
Get this wrong and this could mean the end… :-) some funny, some not…
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Can you Deep Throat? Do you like the taste of yourself?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
* Give a rating for each one (0-100)
46~ Have you ever used furniture, or other types of things to aid you while having sex?
18~ Who/when was your first “crush”?
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 mind if your partner watched it? How about together vs alone?
What have you learned about yourself that you did not before this?
How well do you know me? And some of your thoughts about me
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
The Ice Breaker Questions
Teacher/Student Stranger/One Night Stand
15- What's your favorite saying? What word or phrase is your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you think this brought you closer together?
What have you learned about me that was new and/or surprising?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
1- What was your first impression of me? Has it changed?
You know that I will be 100% truthful, so ask.
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
10- What is your favorite family tradition? What’s your least favorite?
30~ What's something unexpected that turns you on?
5- Have you ever been hypnotized? Would you allow yourself to be?
Have you ever? Care to Share?
26~ What side of the bed do you sleep on?
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?
Would you ever want to be woken up with oral and/or intercourse?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
40~ What’s the weirdest place you’ve ever had sex?
17- Have you ever done drugs? Which ones? How often?
21~ What was the best date you ever went on? What has been the worst?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
83~ How do you feel about Porn?
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 do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
44~ Care to share something about yourself that no one else knows about you?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What is your favorite toy? Ever wanted to try a specific toy?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
Do you watch it? What is your favorite?
What would you say to prove to yourself that it was really you?
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,
9- Is there something you’ve always wanted to ask me but you’re afraid?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Nurse/Patient Celebrity/Fan
49~ How many times have you been married? Why did they end?
Escort/Client Job Applicant/Hiring Manager
36~ What is your favorite time of day to have sex/make love?
12- What is the weirdest thing you've ever eaten?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
28- What are some things that people do that irritate you?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
14- What's your favorite dessert? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
How many times do you think you have “made love”?
38~ Share your most embarrassing sexual memory?
Would you do it again, and would you rather 2 females or 2 males?
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?
28~ What are some things that turn on? What is your biggest turn on?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
If yes, what?
How about if they talk dirty and/or call you names?
65~ Describe the best orgasm you’ve ever had? Care to share?
23- What is your dream job? What was it as a child?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
19~ Who/when was your first “heartbreak”?
Repairman/Lonely Wife Virgin/Experienced
Family Relation Age Play
10- List 5 of your top pet peeves.
If NO, would you ever have one? Would it be with 2 men or 2 women?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
What is your favorite position? Why?
1~ How old were you when you had your first kiss? Who? Care to Share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Over time has your thoughts on sex changed?
Any that are a turn off?
4- For a pet, Cat, dog or other?
6- Do you have dreams? Can you remember them? What do you usually dream about?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Any that are a turn off?
80~ Share your top three fantasies/desires. (Be detailed) 😊
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Do you like the “69” position? Do you prefer to be on top or bottom?
What is your view on sex? Meaning, When/Where/ How often/
84~ How do you feel about reading/listening to adult stories?
11- How about if they like a certain sports team? 12-How about drinking too much?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Does the thought excite you? Care to share?
61~ How willing would you be to try new sexual positions?
9~ How many times over your lifetime do you think you have had sex so far?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
11- What's your favorite restaurant? What’s your least favorite?
50~ How many children do you have? What are their ages?
19- Do/have you smoked? What do you prefer? How often?
If you say it, I will stop, and we can talk about it when you are ready.
62~ Have you used adult toys?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
29- How superstitious are you?
If YES, was it with 2 men or 2 women? Did you enjoy it?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Do you have a favorite? Is it ok if your partner does?
Nothing too Serious
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Please share Did you stop?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
*** Random Questions ***
3- What Superhero or Superpower would you want to be/have?
22- Do you have any birth marks? How about scars? Care to share how you got them?
32- What's your greatest talent? Can I see it right now?
52~ Are you willing to make “those types” of bets with your partner?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
*** Questions About Me ***
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
What was the longest? What was the shortest?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
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…
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
48~ Do you have any siblings? Are you close to your family?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
13- What is the craziest/scariest thing you've ever done?
39~ What are your love languages?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
71~ Would you give your partner a hand or foot job? Would you receive one?
14- What is an embarrassing moment in your life? How about your most embarrassing?
*** Questions about Relationships/Past ***
92~ Everyone needs a “safe” word. What is yours?
(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…)
34- Ever been to a concert? What was your favorite? Who would you like to see?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
9- What’s your favorite season and why? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
29~ What are some things that turn you off? What is your biggest turn off?
92~ Have you ever had or have an STD? How many? What was it?
10~ How many dates are necessary before you to have sex with someone?
76~ Have you had a threesome? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
33- If you could visit any time period, when would you pick? Please explain why?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
That one or two things that made you go hmmmm, OMG or wow!