What is the most interesting question you can ask to get to know someone?
11.06.2025 09:15
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)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Master/Slave Boss/Maid
39~ What are your love languages?
22- Do you have any birth marks? How about scars? Care to share how you got them?
31- If given a chance to be immortal, would you take it? Why?
How do you feel about Donald Trump signing an executive order that says there are only two genders?
25~ How do you feel about PDA? (Public Display of Affection)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Will you share your wife? Can she take both of us at the same time?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
61~ How willing would you be to try new sexual positions?
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?
What is your favorite toy? Ever wanted to try a specific toy?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Why do narcissists and especially covert narcissists always play the victim?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Get this wrong and this could mean the end… :-) some funny, some not…
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
What is something you have to share?
18- How often do you drink alcohol? What is your favorite drink?
Would /have you ever given your partner a lap dance and Striptease?
Would you ever want to be woken up with oral and/or intercourse?
Why did Donald Trump and Melania Trump sleep in different rooms?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
If yes, what?
32- What's your greatest talent? Can I see it right now?
Chris Conley announces his retirement - NBC Sports
Can you Deep Throat? Do you like the taste of yourself?
You know that I will be 100% truthful, so ask.
11- What's your favorite restaurant? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Jonathan Anderson has been appointed sole creative director of Dior - Vogue Business
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?
15- What's your favorite saying? What word or phrase is your least favorite?
Model/Photographer Police/Criminal
First Day of Roots Picnic Was an "Absolute Disaster," Fans Say - Philadelphia Magazine
81~ Do you have any kinks and/or fetishes?
84~ How do you feel about reading/listening to adult stories?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
70~ Would/do you have/like anal sex?
19- Do/have you smoked? What do you prefer? How often?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
34~ Do you like the lights on or off during sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
48~ Do you have any siblings? Are you close to your family?
1- What’s your favorite animal? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? 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?
Have you ever? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
42~ What’s your biggest regret in life?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Any that are a turn off?
That one or two things that made you go hmmmm, OMG or wow!
*** Questions about Relationships/Past ***
45~ How do you feel about me blindfolding you? How about blindfolding me?
Family Relation Age Play
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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?
14- What's your favorite dessert? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
65~ Describe the best orgasm you’ve ever had? Care to share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Do you like it when they show and tell you what they want?
17- What’s your favorite holiday? What’s your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
26~ What side of the bed do you sleep on?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
38~ Share your most embarrassing sexual memory?
Prisoner/Prison Guard Landlord/Tenant
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If YES, was it with 2 men or 2 women? Did you enjoy it?
47~ What would be your dream job and why?
51~ Are you willing to play adult games with your partner?
1- What was your first impression of me? Has it changed?
28~ What are some things that turn on? What is your biggest turn on?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Will you cheat again? How can, you be sure? Define what cheating is to you.
29- How superstitious are you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
76~ Have you had a threesome? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Do you have a favorite? Is it ok if your partner does?
7- What if a person smells a certain way? 8- How about smoking?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
92~ Have you ever had or have an STD? How many? What was it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
The Ice Breaker Questions
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
Nothing too Serious
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Nurse/Patient Celebrity/Fan
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
5~ When you first started having sex, was it what you thought it would be?
3- What Superhero or Superpower would you want to be/have?
What was the longest? What was the shortest?
28- What are some things that people do that irritate you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
33- Beach or Mountains? Or is there another place to like better?
What have you learned about me that was new and/or surprising?
44~ Care to share something about yourself that no one else knows about you?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
80~ Share your top three fantasies/desires. (Be detailed) 😊
18- What’s your favorite way to relax after a long day? What’s your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
10~ How many dates are necessary before you to have sex with someone?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
36~ What is your favorite time of day to have sex/make love?
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…
Over time has your thoughts on sex changed?
4- For a pet, Cat, dog or other?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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~ How many times over your lifetime do you think you have had sex so far?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How many times do you think you have “made love”?
33- If you could visit any time period, when would you pick? Please explain why?
21~ What was the best date you ever went on? What has been the worst?
13- What is the craziest/scariest thing you've ever done?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
49~ How many times have you been married? Why did they end?
What is your view on sex? Meaning, When/Where/ How often/
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
12- What is the weirdest thing you've ever eaten?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
89~ Do you like taking showers together?
11~ Have you ever been caught by your parents or children or others while having sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
*** Questions About Me ***
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?
82~ Do you have any fantasies involving Role-Playing?
53~ How much can you tell me about the one thing you are most passionate about?
If you say it, I will stop, and we can talk about it when you are ready.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Any that are a turn off?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
37- Do you like your name? If you could change it, what would you change it too?
Do you think this brought you closer together?
Doctor/Nurse Stripper/Client
Does the thought excite you? Care to share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
92~ Everyone needs a “safe” word. What is yours?
Would you mind if your partner watched it? How about together vs alone?
* Give a rating for each one (0-100)
8- What are your thoughts on politics?
6- Do you have dreams? Can you remember them? What do you usually dream about?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
62~ Have you used adult toys?
What do you dislike about me? I asked you to be 100% honest.
83~ How do you feel about Porn?
71~ Would you give your partner a hand or foot job? Would you receive one?
9- Is there something you’ve always wanted to ask me but you’re afraid?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
9- What’s your favorite season and why? What’s your least favorite?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
5- Have you ever been hypnotized? Would you allow yourself to be?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
40~ What’s the weirdest place you’ve ever had sex?
How about if they talk dirty and/or call you names?
22- What is your favorite childhood memory? What is your least favorite?
*** What’s Your 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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
19~ Who/when was your first “heartbreak”?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
11- How about if they like a certain sports team? 12-How about drinking too much?
Do you like the “69” position? Do you prefer to be on top or bottom?
15- What bad habit do you wish you could quit? Do you have any addictions?
36- Do you play video games? What is your favorite? Do you a least favorite?
17- Have you ever done drugs? Which ones? How often?
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?
30~ What's something unexpected that turns you on?
Would you read them together?
If NO, would you ever have one? Would it be with 2 men or 2 women?
12- What’s your favorite food? What’s your least favorite?
6- What’s your favorite TV series? 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)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
7- What are your thoughts on religion? Is there an afterlife?
What would you say to prove to yourself that it was really you?
*** Deal Breaker Questions ***
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
9- If you could have three wishes, what would they be? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
What is your favorite position? Why?
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 old are you? Male or Female?
Do you watch it? What is your favorite?
23- What is your dream job? What was it as a child?
If you win, what will you make them do?
21- What's your favorite way to spend a weekend or time off?
Teacher/Student Stranger/One Night Stand
What have you learned about yourself that you did not before this?
13- How about having a certain hair cut/style?
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…
1~ How old were you when you had your first kiss? Who? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Escort/Client Job Applicant/Hiring Manager
34- Ever been to a concert? What was your favorite? Who would you like to see?
48~ Have you ever paid or been paid for sex?
51~ What tends to bring a smile to your face?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Please share Did you stop?
52~ Are you willing to make “those types” of bets with your partner?
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
(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…)
10- List 5 of your top pet peeves.
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
I would allow you to do it… What would you do to me?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
2- What’s your favorite color? Do you a least favorite?
*** Random Questions ***
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
19- What’s your favorite fairytale? What’s your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
50~ How many children do you have? What are their ages?
How many partners have you had oral sex with? Who? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How well do you know me? And some of your thoughts about me
15~ Have you ever been “in love”? Who? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
27- What was/ is nickname? Does it have a meaning behind it?
52~ What are your hobbies?
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?