What is the most interesting question you can ask to get to know someone?
09.06.2025 02:47
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would /have you ever given your partner a lap dance and Striptease?
29~ What are some things that turn you off? What is your biggest turn off?
Has your mother ever walked in on you at an inappropriate time?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
10- List 5 of your top pet peeves.
What would it take for you to consider yourself a "Swiftie" like Flavor Flav?
83~ How do you feel about Porn?
15- What's your favorite saying? What word or phrase is your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Why is there no great temptress figure in any of Tolkien’s major works?
How many times do you think you have “made love”?
21- What's your favorite way to spend a weekend or time off?
11~ Have you ever been caught by your parents or children or others while having sex?
Why is blood sugar ranging from 70-180 in a day and checked through a glucometer?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
39~ What are your love languages?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Did Trump show us once again that he is a master debater?
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…
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Pokemon Scarlet And Violet's Free Switch 2 Update Is Now Live - GameSpot
Repairman/Lonely Wife Virgin/Experienced
Do you like it when they show and tell you what they want?
52~ What are your hobbies?
How do you get a teenage boy to care about hygiene?
(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…)
52~ Are you willing to make “those types” of bets with your partner?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
iOS 19: All the rumored changes Apple could be bringing to its new operating system - TechCrunch
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Get this wrong and this could mean the end… :-) some funny, some not…
Why can’t my wife just accept the fact that I’m going to cheat?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would you do it again, and would you rather 2 females or 2 males?
48~ Do you have any siblings? Are you close to your family?
A Cosmic Tech Mystery Results in Literal Lost Souls in This Sci-Fi Short Story - Gizmodo
11- How about if they like a certain sports team? 12-How about drinking too much?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What CIA front organizations operated in the United States during the 1960s?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you think this brought you closer together?
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25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
13- How about having a certain hair cut/style?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
80~ Share your top three fantasies/desires. (Be detailed) 😊
1- What’s your favorite animal? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Doctor/Nurse Stripper/Client
How well do you know me? And some of your thoughts about me
3- Should Pluto still be considered a planet? 4- How about smoking?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
If you win, what will you make them do?
27- What was/ is nickname? Does it have a meaning behind it?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
That one or two things that made you go hmmmm, OMG or wow!
Does the thought excite you? Care to share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
22- What is your favorite childhood memory? What is your least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
5- Have you ever been hypnotized? Would you allow yourself to be?
*** Questions About Me ***
*** Deal Breaker Questions ***
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- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
71~ Would you give your partner a hand or foot job? Would you receive one?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What is your favorite position? Why?
What is your view on sex? Meaning, When/Where/ How often/
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Model/Photographer Police/Criminal
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
61~ How willing would you be to try new sexual positions?
You know that I will be 100% truthful, so ask.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Do you have a favorite? Is it ok if your partner does?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
26~ What side of the bed do you sleep on?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
7- What are your thoughts on religion? Is there an afterlife?
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 clean every part of your body with my soapy hands and fingers?
12- What is the weirdest thing you've ever eaten?
Please share Did you stop?
*** What’s Your Favorite…? ***
49~ How many times have you been married? Why did they end?
29- How superstitious are you?
70~ Would/do you have/like anal sex?
1- What was your first impression of me? Has it changed?
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)
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?
36~ What is your favorite time of day to have sex/make love?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
*** Questions about Relationships/Past ***
Would you mind if your partner watched it? How about together vs alone?
76~ Have you had a threesome? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
10- What is your favorite family tradition? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Over time has your thoughts on sex changed?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What have you learned about me that was new and/or surprising?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
5~ When you first started having sex, was it what you thought it would be?
62~ Have you used adult toys?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
23- What is your dream job? What was it as a child?
14- What's your favorite dessert? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
42~ What’s your biggest regret in life?
Do you like the “69” position? Do you prefer to be on top or bottom?
Any that are a turn off?
1~ How old were you when you had your first kiss? Who? Care to Share?
Family Relation Age Play
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
28~ What are some things that turn on? What is your biggest turn on?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Nothing too Serious
What was the longest? What was the shortest?
Any that are a turn off?
33- If you could visit any time period, when would you pick? Please explain why?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
The Ice Breaker Questions
What is your favorite toy? Ever wanted to try a specific toy?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
30~ What's something unexpected that turns you on?
10~ How many dates are necessary before you to have sex with someone?
92~ Everyone needs a “safe” word. What is yours?
3- What Superhero or Superpower would you want to be/have?
How about if they talk dirty and/or call you names?
Prisoner/Prison Guard Landlord/Tenant
19~ Who/when was your first “heartbreak”?
8- What's your favorite flavor of ice cream? Do you a least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
89~ Do you like taking showers together?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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?
28- What are some things that people do that irritate you?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
19- Do/have you smoked? What do you prefer? How often?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
14- What is an embarrassing moment in your life? How about your most embarrassing?
If you say it, I will stop, and we can talk about it when you are ready.
Nurse/Patient Celebrity/Fan
24~ What are your expectations in a relationship? (I know a very big question, take your time)
92~ Have you ever had or have an STD? How many? What was it?
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?
50~ How many children do you have? What are their ages?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
25~ How do you feel about PDA? (Public Display of Affection)
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)
11- List at least 5 things on your bucket list. Have you done any of them already?
15~ Have you ever been “in love”? Who? Care to Share?
33- Beach or Mountains? Or is there another place to like better?
36- Do you play video games? What is your favorite? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Have you ever? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
38~ Share your most embarrassing sexual memory?
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?
9- What’s your favorite season and why? What’s your least favorite?
8- What are your thoughts on politics?
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?
13~ Is there a difference between, making love, having sex, and fucking?
51~ Are you willing to play adult games with your partner?
What would you say to prove to yourself that it was really you?
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?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
45~ How do you feel about me blindfolding you? How about blindfolding me?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
20- What’s your favorite candy? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
48~ Have you ever paid or been paid for sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
Do you watch it? What is your favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What do you dislike about me? I asked you to be 100% honest.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
If yes, what?
4- For a pet, Cat, dog or other?
3- What’s your favorite smell? Do you a least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
18~ Who/when was your first “crush”?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
81~ Do you have any kinks and/or fetishes?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
53~ How much can you tell me about the one thing you are most passionate about?
2- What’s your favorite color? Do you a least favorite?
Master/Slave Boss/Maid
Can you Deep Throat? Do you like the taste of yourself?
Would you read them together?
How old are you? Male or Female?
* Give a rating for each one (0-100)
9- Is there something you’ve always wanted to ask me but you’re afraid?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Escort/Client Job Applicant/Hiring Manager
I would allow you to do it… What would you do to me?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
44~ Care to share something about yourself that no one else knows about you?
*** Random Questions ***
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,
How many partners have you had oral sex with? 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…
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
32- What's your greatest talent? Can I see it right now?
51~ What tends to bring a smile to your face?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
11- What's your favorite restaurant? What’s your least favorite?
12- What’s your favorite food? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
Would you ever want to be woken up with oral and/or intercourse?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
82~ Do you have any fantasies involving Role-Playing?
34~ Do you like the lights on or off during sex?
13- What is the craziest/scariest thing you've ever done?
7- What if a person smells a certain way? 8- How about smoking?
19- What’s your favorite fairytale? What’s your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
13- What’s your favorite drink? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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?
9~ How many times over your lifetime do you think you have had sex so far?
65~ Describe the best orgasm you’ve ever had? Care to share?
9- If you could have three wishes, what would they be? Why?
15- What bad habit do you wish you could quit? Do you have any addictions?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?