What is the most interesting question you can ask to get to know someone?
08.06.2025 00:16
60~ How important is oral sex? Do you like receiving? Do you like giving?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
As a teacher, what's the most inappropriate experience you've had with a student?
83~ How do you feel about Porn?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
'Mountainhead' Is Most-Watched HBO Original Film Since 'Bad Education' - Deadline
84~ How do you feel about reading/listening to adult stories?
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?
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)
The Ice Breaker Questions
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
What have you learned about me that was new and/or surprising?
What is your favorite position? Why?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Why do I feel like I want to suck a big dick after injecting meth?
How many partners have you had oral sex with? Who? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Wright State stuns No. 1 Vanderbilt with historic upset in baseball regionals - Yahoo Sports
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What is your view on sex? Meaning, When/Where/ How often/
Broadcom Stock Falls Despite Earnings Beat From AI Chip Maker - Barron's
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
3- Should Pluto still be considered a planet? 4- How about smoking?
19~ Who/when was your first “heartbreak”?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
IndiGo, Delta, Air France-KLM, Virgin Atlantic Announce Partnership - Airways Magazine
Do you shave/trim your pubic hair? For you guys do you shave your balls?
27- What was/ is nickname? Does it have a meaning behind it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Can Djokovic climb the mountain? - Roland Garros
21~ What was the best date you ever went on? What has been the worst?
Will you cheat again? How can, you be sure? Define what cheating is to you.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Supplement health risks to know about, plus a celebrity's 'brutal' infection - Fox News
13- How about having a certain hair cut/style?
What would you say to prove to yourself that it was really you?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
What are some tips for braiding a woman's hair on a date?
Doctor/Nurse Stripper/Client
20- What’s your favorite candy? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
11- What's your favorite restaurant? What’s your least favorite?
2- What’s your favorite color? Do you a least favorite?
Have you ever? Care to Share?
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,
Do you watch it? What is your favorite?
* Give a rating for each one (0-100)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Prisoner/Prison Guard Landlord/Tenant
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
11- How about if they like a certain sports team? 12-How about drinking too much?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Master/Slave Boss/Maid
32- What's your greatest talent? Can I see it right now?
Any that are a turn off?
1~ How old were you when you had your first kiss? Who? Care to Share?
*** Deal Breaker Questions ***
67~ Do you like it when your partner moans and/or is vocal during sex?
92~ Have you ever had or have an STD? How many? What was it?
Do you think this brought you closer together?
65~ Describe the best orgasm you’ve ever had? Care to share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
28- What are some things that people do that irritate you?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
How about if they talk dirty and/or call you names?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
38~ Share your most embarrassing sexual memory?
If NO, would you ever have one? Would it be with 2 men or 2 women?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
29~ What are some things that turn you off? What is your biggest turn off?
How many times do you think you have “made love”?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
61~ How willing would you be to try new sexual positions?
30~ What's something unexpected that turns you on?
53~ How much can you tell me about the one thing you are most passionate about?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
9~ How many times over your lifetime do you think you have had sex so far?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
*** What’s Your Favorite…? ***
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
13- What’s your favorite drink? What’s your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Over time has your thoughts on sex changed?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
If you win, what will you make them do?
40~ What’s the weirdest place you’ve ever had sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
5~ When you first started having sex, was it what you thought it would be?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
7- What are your thoughts on religion? Is there an afterlife?
9- What’s your favorite season and why? What’s your least favorite?
10- List 5 of your top pet peeves.
8- What are your thoughts on politics?
29- How superstitious are you?
*** Random Questions ***
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Escort/Client Job Applicant/Hiring Manager
5- Have you ever been hypnotized? Would you allow yourself to be?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
12- What’s your favorite food? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
22- What is your favorite childhood memory? What is your least favorite?
I would allow you to do it… What would you do to me?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
22- Do you have any birth marks? How about scars? Care to share how you got them?
1- What was your first impression of me? Has it changed?
13- What is the craziest/scariest thing you've ever done?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
81~ Do you have any kinks and/or fetishes?
1- What’s your favorite animal? Do you a least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
How old are you? Male or Female?
Do you like the “69” position? Do you prefer to be on top or bottom?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would you read them together?
92~ Everyone needs a “safe” word. What is yours?
42~ What’s your biggest regret in life?
Do you have a favorite? Is it ok if your partner does?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Teacher/Student Stranger/One Night Stand
31- If given a chance to be immortal, would you take it? Why?
Would /have you ever given your partner a lap dance and Striptease?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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…
52~ What are your hobbies?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
44~ Care to share something about yourself that no one else knows about you?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
You know that I will be 100% truthful, so ask.
That one or two things that made you go hmmmm, OMG or wow!
11- List at least 5 things on your bucket list. Have you done any of them already?
48~ Have you ever paid or been paid for sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
23- What is your dream job? What was it as a child?
3- What Superhero or Superpower would you want to be/have?
51~ What tends to bring a smile to your face?
39~ What are your love languages?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
12- What is the weirdest thing you've ever eaten?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
50~ How many children do you have? What are their ages?
33- If you could visit any time period, when would you pick? Please explain why?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
Model/Photographer Police/Criminal
What have you learned about yourself that you did not before this?
14- What's your favorite dessert? Do you a least favorite?
36~ What is your favorite time of day to have sex/make love?
Do you like it when they show and tell you what they want?
How well do you know me? And some of your thoughts about me
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
76~ Have you had a threesome? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Family Relation Age Play
25~ How do you feel about PDA? (Public Display of Affection)
10~ How many dates are necessary before you to have sex with someone?
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?
70~ Would/do you have/like anal sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
13~ Is there a difference between, making love, having sex, and fucking?
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…
Nurse/Patient Celebrity/Fan
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you do it again, and would you rather 2 females or 2 males?
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?
33- Beach or Mountains? Or is there another place to like better?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
41~ Are there moments in your past that you would want to change? Please share 3 of them.
28~ What are some things that turn on? What is your biggest turn on?
9- If you could have three wishes, what would they be? Why?
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 allow me to clean every part of your body with my soapy hands and fingers?
Any that are a turn off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What was the longest? What was the shortest?
3- What’s your favorite smell? Do you a least favorite?
62~ Have you used adult toys?
Nothing too Serious
22~ What is the best pickup line anyone has ever used on you? What was the worst?
7- What if a person smells a certain way? 8- How about smoking?
49~ How many times have you been married? Why did they end?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
21- What's your favorite way to spend a weekend or time off?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
If yes, what?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
45~ How do you feel about me blindfolding you? How about blindfolding me?
47~ What would be your dream job and why?
Can you Deep Throat? Do you like the taste of yourself?
4- For a pet, Cat, dog or other?
26~ What side of the bed do you sleep on?
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
(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…)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Repairman/Lonely Wife Virgin/Experienced
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
71~ Would you give your partner a hand or foot job? Would you receive one?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
*** Questions about Relationships/Past ***
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Please share Did you stop?
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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
17- Have you ever done drugs? Which ones? How often?
34~ Do you like the lights on or off during sex?
48~ Do you have any siblings? Are you close to your family?
18~ Who/when was your first “crush”?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
89~ Do you like taking showers together?
15~ Have you ever been “in love”? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Get this wrong and this could mean the end… :-) some funny, some not…
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What do you dislike about me? I asked you to be 100% honest.
51~ Are you willing to play adult games with your partner?
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
37- Do you like your name? If you could change it, what would you change it too?
52~ Are you willing to make “those types” of bets with your partner?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would you mind if your partner watched it? How about together vs alone?
82~ Do you have any fantasies involving Role-Playing?
19- What’s your favorite fairytale? What’s your least favorite?
*** Questions About Me ***
Does the thought excite you? Care to share?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?