What is the most interesting question you can ask to get to know someone?
14.06.2025 07:36
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
53~ How much can you tell me about the one thing you are most passionate about?
27- What was/ is nickname? Does it have a meaning behind it?
How do I become mentally strong?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Would you mind if your partner watched it? How about together vs alone?
81~ Do you have any kinks and/or fetishes?
What is one small habit that has transformed your life in unexpected ways?
Doctor/Nurse Stripper/Client
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
K-pop supergroup BTS nears reunion as two more members end military service - The Washington Post
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would you do it again, and would you rather 2 females or 2 males?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What happens psychologically to a man the first time he gets penetrated anally?
37- Do you like your name? If you could change it, what would you change it too?
Nothing too Serious
Do you think this brought you closer together?
Would you join a gym or workout at home and why?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
83~ How do you feel about Porn?
How about if they talk dirty and/or call you names?
Are LGBT people accepted in Japan?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
52~ Are you willing to make “those types” of bets with your partner?
If you were a writer for HBO, how would you rewrite the final season of Game of Thrones?
61~ How willing would you be to try new sexual positions?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
11~ Have you ever been caught by your parents or children or others while having sex?
Why did my ex move on so fast, we have only been broken up for 2 weeks?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
50~ How many children do you have? What are their ages?
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?
92~ Everyone needs a “safe” word. What is yours?
84~ How do you feel about reading/listening to adult stories?
Do you watch it? What is your favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
What toxic behavior has been normalized by society?
34~ Do you like the lights on or off during sex?
How many partners have you had oral sex with? Who? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
12- What is the weirdest thing you've ever eaten?
* Give a rating for each one (0-100)
Why am I so jealous towards couples? Why am I tired of being single and feel my life is over?
92~ Have you ever had or have an STD? How many? What was it?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
1~ How old were you when you had your first kiss? Who? Care to Share?
3- What Superhero or Superpower would you want to be/have?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
*** What’s Your Favorite…? ***
22- What is your favorite childhood memory? What is your least favorite?
38~ Share your most embarrassing sexual memory?
*** Questions About Me ***
Do you like it when they show and tell you what they want?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
33- Beach or Mountains? Or is there another place to like better?
17- What’s your favorite holiday? What’s your least favorite?
Prisoner/Prison Guard Landlord/Tenant
What have you learned about yourself that you did not before this?
45~ How do you feel about me blindfolding you? How about blindfolding me?
60~ How important is oral sex? Do you like receiving? Do you like giving?
If YES, was it with 2 men or 2 women? Did you enjoy it?
25~ How do you feel about PDA? (Public Display of Affection)
Do you like the “69” position? Do you prefer to be on top or bottom?
44~ Care to share something about yourself that no one else knows about you?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
29- How superstitious are you?
3- What’s your favorite smell? Do you a least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
8- What's your favorite flavor of ice cream? Do you a least favorite?
If yes, what?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
7- What if a person smells a certain way? 8- How about smoking?
Escort/Client Job Applicant/Hiring Manager
65~ Describe the best orgasm you’ve ever had? Care to share?
If you say it, I will stop, and we can talk about it when you are ready.
30~ What's something unexpected that turns you on?
19- Do/have you smoked? What do you prefer? How often?
5- Have you ever been hypnotized? Would you allow yourself to be?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
51~ What tends to bring a smile to your face?
10- What is your favorite family tradition? What’s your least favorite?
Any that are a turn off?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
23- What is your dream job? What was it as a child?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
9- What’s your favorite season and why? What’s your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
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?
10- List 5 of your top pet peeves.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Nurse/Patient Celebrity/Fan
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Would you ever want to be woken up with oral and/or intercourse?
21- What's your favorite way to spend a weekend or time off?
82~ Do you have any fantasies involving Role-Playing?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
89~ Do you like taking showers together?
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?
11- What's your favorite restaurant? What’s your least favorite?
What is your favorite position? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
47~ What would be your dream job and why?
How well do you know me? And some of your thoughts about me
*** Questions about Relationships/Past ***
Over time has your thoughts on sex changed?
What have you learned about me that was new and/or surprising?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
42~ What’s your biggest regret in life?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
If you win, what will you make them do?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
(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…)
13- What’s your favorite drink? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Master/Slave Boss/Maid
48~ Do you have any siblings? Are you close to your family?
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)
13- How about having a certain hair cut/style?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
18~ Who/when was your first “crush”?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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…
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Please share Did you stop?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Family Relation Age Play
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
Can you Deep Throat? Do you like the taste of yourself?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
What was the longest? What was the shortest?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Do you have a favorite? Is it ok if your partner does?
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,
Model/Photographer Police/Criminal
Would you allow me to clean every part of your body with my soapy hands and fingers?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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…
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
The Ice Breaker Questions
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
8- What are your thoughts on politics?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Teacher/Student Stranger/One Night Stand
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
31- If given a chance to be immortal, would you take it? Why?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
49~ How many times have you been married? Why did they end?
18- How often do you drink alcohol? What is your favorite drink?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Any that are a turn off?
13~ Is there a difference between, making love, having sex, and fucking?
17- Have you ever done drugs? Which ones? How often?
6- Do you have dreams? Can you remember them? What do you usually dream about?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
How old are you? Male or Female?
Have you ever? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
4- For a pet, Cat, dog or other?
2- What’s your favorite color? Do you a least favorite?
28- What are some things that people do that irritate you?
21~ What was the best date you ever went on? What has been the worst?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
15- What's your favorite saying? What word or phrase is your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
62~ Have you used adult toys?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Random Questions ***
29~ What are some things that turn you off? What is your biggest turn off?
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?
26~ What side of the bed do you sleep on?
Would /have you ever given your partner a lap dance and Striptease?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
13- What is the craziest/scariest thing you've ever done?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
70~ Would/do you have/like anal sex?
You know that I will be 100% truthful, so ask.
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How many times do you think you have “made love”?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Would you read them together?
What is your view on sex? Meaning, When/Where/ How often/
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
9- If you could have three wishes, what would they be? Why?
5~ When you first started having sex, was it what you thought it would be?
1- What was your first impression of me? Has it changed?
1- What’s your favorite animal? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
22- Do you have any birth marks? How about scars? Care to share how you got them?
What would you say to prove to yourself that it was really you?
7- What are your thoughts on religion? Is there an afterlife?
11- List at least 5 things on your bucket list. Have you done any of them already?
19- What’s your favorite fairytale? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
If NO, would you ever have one? Would it be with 2 men or 2 women?
39~ What are your love languages?
That one or two things that made you go hmmmm, OMG or wow!
12- What’s your favorite food? What’s your least favorite?
Does the thought excite you? Care to share?
36- Do you play video games? What is your favorite? Do you a least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
33- If you could visit any time period, when would you pick? Please explain why?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
76~ Have you had a threesome? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
19~ Who/when was your first “heartbreak”?
14- What's your favorite dessert? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
What do you dislike about me? I asked you to be 100% honest.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Get this wrong and this could mean the end… :-) some funny, some not…
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
*** Deal Breaker Questions ***
80~ Share your top three fantasies/desires. (Be detailed) 😊
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
52~ What are your hobbies?
20- What’s your favorite candy? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
I would allow you to do it… What would you do to me?
51~ Are you willing to play adult games with your partner?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
40~ What’s the weirdest place you’ve ever had sex?
15- What bad habit do you wish you could quit? Do you have any addictions?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
28~ What are some things that turn on? What is your biggest turn on?