What is the most interesting question you can ask to get to know someone?
08.06.2025 04:26
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Why do most people care so much about what others think? Are they afraid of society norms?
13- What is the craziest/scariest thing you've ever done?
19~ Who/when was your first “heartbreak”?
18- How often do you drink alcohol? What is your favorite drink?
Scoop: Treasury officials defend "revenge tax" from wary GOP senators - Axios
5~ When you first started having sex, was it what you thought it would be?
80~ Share your top three fantasies/desires. (Be detailed) 😊
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Can Djokovic climb the mountain? - Roland Garros
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
34~ Do you like the lights on or off during sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Apple’s leaked 45W MagSafe charger is first to support Qi2.2 - The Verge
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Family Relation Age Play
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
17 more WA Rite Aid stores, including 4 Bartell Drugs, to shutter - The Seattle Times
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
28- What are some things that people do that irritate you?
*** Random Questions ***
Have you ever had sex with your mother-in-law? If so, how was it and did your wife ever find out?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
36- Do you play video games? What is your favorite? Do you a least favorite?
How many times do you think you have “made love”?
What is the reason for The Acolyte (2024 series) having poor reception among Star Wars fans?
*** What’s Your Favorite…? ***
What would you say to prove to yourself that it was really you?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
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?
Do you like it when they show and tell you what they want?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
13- How about having a certain hair cut/style?
15- What's your favorite saying? What word or phrase is your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
22- Do you have any birth marks? How about scars? Care to share how you got them?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
You know that I will be 100% truthful, so ask.
11- How about if they like a certain sports team? 12-How about drinking too much?
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…
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?
48~ Have you ever paid or been paid for sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Can you Deep Throat? Do you like the taste of yourself?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Any that are a turn off?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
92~ Have you ever had or have an STD? How many? What was it?
Get this wrong and this could mean the end… :-) some funny, some not…
52~ Are you willing to make “those types” of bets with your partner?
18~ Who/when was your first “crush”?
48~ Do you have any siblings? Are you close to your family?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
25~ How do you feel about PDA? (Public Display of Affection)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
70~ Would/do you have/like anal sex?
20- What’s your favorite candy? What’s your least favorite?
Have you ever? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
How many partners have you had oral sex with? Who? Care to Share?
26~ What side of the bed do you sleep on?
82~ Do you have any fantasies involving Role-Playing?
Would you do it again, and would you rather 2 females or 2 males?
10- List 5 of your top pet peeves.
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What do you dislike about me? I asked you to be 100% honest.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
23- What is your dream job? What was it as a child?
What have you learned about yourself that you did not before this?
Master/Slave Boss/Maid
92~ Everyone needs a “safe” word. What is yours?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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…
29- How superstitious are you?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What is your view on sex? Meaning, When/Where/ How often/
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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
*** Deal Breaker Questions ***
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
47~ What would be your dream job and why?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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,
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
9- What’s your favorite season and why? What’s your least favorite?
3- What Superhero or Superpower would you want to be/have?
Do you think this brought you closer together?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
4- For a pet, Cat, dog or other?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
84~ How do you feel about reading/listening to adult stories?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
33- Beach or Mountains? Or is there another place to like better?
What is your favorite toy? Ever wanted to try a specific toy?
76~ Have you had a threesome? Care to Share?
62~ Have you used adult toys?
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)
Please share Did you stop?
21- What's your favorite way to spend a weekend or time off?
44~ Care to share something about yourself that no one else knows about you?
What is your favorite position? Why?
7- What are your thoughts on religion? Is there an afterlife?
6- What’s your favorite TV series? Do you have a favorite genre? 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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Nurse/Patient Celebrity/Fan
89~ Do you like taking showers together?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What was the longest? What was the shortest?
If yes, what?
19- What’s your favorite fairytale? What’s your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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)
45~ How do you feel about me blindfolding you? How about blindfolding me?
40~ What’s the weirdest place you’ve ever had sex?
Any that are a turn off?
34- Ever been to a concert? What was your favorite? Who would you like to see?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
1~ How old were you when you had your first kiss? Who? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
(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…)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
11~ Have you ever been caught by your parents or children or others while having sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8- What are your thoughts on politics?
9- If you could have three wishes, what would they be? Why?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
53~ How much can you tell me about the one thing you are most passionate about?
How well do you know me? And some of your thoughts about me
49~ How many times have you been married? Why did they end?
36~ What is your favorite time of day to have sex/make love?
17- What’s your favorite holiday? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
8- What's your favorite flavor of ice cream? Do you a least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
15~ Have you ever been “in love”? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3- What’s your favorite smell? Do you a least favorite?
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
42~ What’s your biggest regret in life?
How old are you? Male or Female?
7- What if a person smells a certain way? 8- How about smoking?
14- What's your favorite dessert? Do you a least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
22- What is your favorite childhood memory? What is your least favorite?
83~ How do you feel about Porn?
11- What's your favorite restaurant? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
30~ What's something unexpected that turns you on?
5- Have you ever been hypnotized? Would you allow yourself to be?
That one or two things that made you go hmmmm, OMG or wow!
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
21~ What was the best date you ever went on? What has been the worst?
I would allow you to do it… What would you do to me?
Would /have you ever given your partner a lap dance and Striptease?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
29~ What are some things that turn you off? What is your biggest turn off?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Model/Photographer Police/Criminal
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
Teacher/Student Stranger/One Night Stand
38~ Share your most embarrassing sexual memory?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you allow me to clean every part of your body with my soapy hands and fingers?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
67~ Do you like it when your partner moans and/or is vocal during sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
12- What’s your favorite food? What’s your least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
81~ Do you have any kinks and/or fetishes?
50~ How many children do you have? What are their ages?
11- List at least 5 things on your bucket list. Have you done any of them already?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
32- What's your greatest talent? Can I see it right now?
How about if they talk dirty and/or call you names?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
19- Do/have you smoked? What do you prefer? How often?
Nothing too Serious
Does the thought excite you? Care to share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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.
13- What’s your favorite drink? What’s your least favorite?
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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Repairman/Lonely Wife Virgin/Experienced
If you win, what will you make them do?
Do you like the “69” position? Do you prefer to be on top or bottom?
The Ice Breaker Questions
60~ How important is oral sex? Do you like receiving? Do you like giving?
9~ How many times over your lifetime do you think you have had sex so far?
12- What is the weirdest thing you've ever eaten?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
* Give a rating for each one (0-100)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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~ Is there a difference between, making love, having sex, and fucking?
39~ What are your love languages?
Doctor/Nurse Stripper/Client
Do you watch it? What is your favorite?
17- Have you ever done drugs? Which ones? How often?
*** Questions About Me ***
51~ What tends to bring a smile to your face?
If you say it, I will stop, and we can talk about it when you are ready.
52~ What are your hobbies?
65~ Describe the best orgasm you’ve ever had? Care to share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
61~ How willing would you be to try new sexual positions?
1- What was your first impression of me? Has it changed?
71~ Would you give your partner a hand or foot job? Would you receive one?
2- What’s your favorite color? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
*** Questions about Relationships/Past ***
Would you read them together?
27- What was/ is nickname? Does it have a meaning behind it?
Over time has your thoughts on sex changed?
What have you learned about me that was new and/or surprising?
10- What is your favorite family tradition? What’s your least favorite?
51~ Are you willing to play adult games with your partner?
If NO, would you ever have one? Would it be with 2 men or 2 women?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Will you cheat again? How can, you be sure? Define what cheating is to you.
Would you mind if your partner watched it? How about together vs alone?
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)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Do you have a favorite? Is it ok if your partner does?
28~ What are some things that turn on? What is your biggest turn on?