What is the most interesting question you can ask to get to know someone?
11.06.2025 13:41
I would allow you to do it… What would you do to me?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Will you cheat again? How can, you be sure? Define what cheating is to you.
5- Have you ever been hypnotized? Would you allow yourself to be?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
How can I control my daily masturbating habit?
67~ Do you like it when your partner moans and/or is vocal during sex?
*** Deal Breaker Questions ***
(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…)
Inhibitory Neurons May Hold the Key to Spatial Learning and Memory - Neuroscience News
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Why do people say "tall, dark, and handsome" when they actually mean "tall, white, and handsome"?
9- If you could have three wishes, what would they be? Why?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Tomatoes Recalled Over 'High Risk of Illness or Death' - Newser
40~ What’s the weirdest place you’ve ever had sex?
Over time has your thoughts on sex changed?
47~ What would be your dream job and why?
The Largest Black Hole Jet Ever Found Is 3 Times the Size of the Milky Way - The Daily Galaxy
Have you ever? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do guys ever want to suck a dick even though they are straight?
22- What is your favorite childhood memory? What is your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Are you happy that soon we will never hear from Kamala Jones again?
Please share Did you stop?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
1- What’s your favorite animal? Do you a least favorite?
3- What Superhero or Superpower would you want to be/have?
Redefining physics to roll a ball vertically - Phys.org
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
1~ How old were you when you had your first kiss? Who? Care to Share?
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)
Jessica Alba sunbathes in tiny bikini while ‘channeling chill’ on wellness getaway - Page Six
36- Do you play video games? What is your favorite? Do you a least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What can you do if you are a full-grown adult, but never experienced being a child?
71~ Would you give your partner a hand or foot job? Would you receive one?
What is your view on sex? Meaning, When/Where/ How often/
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,
Elon Musk’s Neuralink closes a $650M Series E - TechCrunch
14- What's your favorite dessert? Do you a least favorite?
Nurse/Patient Celebrity/Fan
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
70~ Would/do you have/like anal sex?
39~ What are your love languages?
32- What's your greatest talent? Can I see it right now?
Would you mind if your partner watched it? How about together vs alone?
12- What is the weirdest thing you've ever eaten?
81~ Do you have any kinks and/or fetishes?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
What was the longest? What was the shortest?
* Give a rating for each one (0-100)
61~ How willing would you be to try new sexual positions?
What have you learned about me that was new and/or surprising?
27- What was/ is nickname? Does it have a meaning behind it?
65~ Describe the best orgasm you’ve ever had? Care to share?
That one or two things that made you go hmmmm, OMG or wow!
7- What if a person smells a certain way? 8- How about smoking?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Prisoner/Prison Guard Landlord/Tenant
What have you learned about yourself that you did not before this?
If yes, what?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Will you kiss after your partner has gone down on you? Swallow or spit semen?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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?
10~ How many dates are necessary before you to have sex with someone?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
Master/Slave Boss/Maid
52~ Are you willing to make “those types” of bets with your partner?
Do you like it when they show and tell you what they want?
11~ Have you ever been caught by your parents or children or others while having sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
28~ What are some things that turn on? What is your biggest turn on?
51~ What tends to bring a smile to your face?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
If you say it, I will stop, and we can talk about it when you are ready.
48~ Have you ever paid or been paid for sex?
20- What’s your favorite candy? What’s your least favorite?
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?
42~ What’s your biggest regret in life?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
Any that are a turn off?
33- Beach or Mountains? Or is there another place to like better?
You know that I will be 100% truthful, so ask.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
3- Should Pluto still be considered a planet? 4- How about smoking?
5~ When you first started having sex, was it what you thought it would be?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
34- Ever been to a concert? What was your favorite? Who would you like to see?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
82~ Do you have any fantasies involving Role-Playing?
89~ Do you like taking showers together?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would you allow me to clean every part of your body with my soapy hands and fingers?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Escort/Client Job Applicant/Hiring Manager
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
45~ How do you feel about me blindfolding you? How about blindfolding me?
13- How about having a certain hair cut/style?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
18- How often do you drink alcohol? What is your favorite drink?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
9- Is there something you’ve always wanted to ask me but you’re afraid?
21- What's your favorite way to spend a weekend or time off?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
*** Questions about Relationships/Past ***
2- What’s your favorite color? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
17- Have you ever done drugs? Which ones? How often?
83~ How do you feel about Porn?
Do you like the “69” position? Do you prefer to be on top or bottom?
21~ What was the best date you ever went on? What has been the worst?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What is your favorite toy? Ever wanted to try a specific toy?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Do you have a favorite? Is it ok if your partner does?
9- What’s your favorite season and why? What’s your least favorite?
28- What are some things that people do that irritate you?
How about if they talk dirty and/or call you names?
10- List 5 of your top pet peeves.
What would you say to prove to yourself that it was really you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
60~ How important is oral sex? Do you like receiving? Do you like giving?
*** Questions About Me ***
48~ Do you have any siblings? Are you close to your family?
44~ Care to share something about yourself that no one else knows about you?
19- What’s your favorite fairytale? What’s your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
15- What's your favorite saying? What word or phrase is your least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Model/Photographer Police/Criminal
17- What’s your favorite holiday? What’s your least favorite?
Do you think this brought you closer together?
*** What’s Your Favorite…? ***
The Ice Breaker Questions
11- What's your favorite restaurant? What’s your least favorite?
51~ Are you willing to play adult games with your partner?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
19- Do/have you smoked? What do you prefer? How often?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
If YES, was it with 2 men or 2 women? Did you enjoy it?
15- What bad habit do you wish you could quit? Do you have any addictions?
37- Do you like your name? If you could change it, what would you change it too?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How many times do you think you have “made love”?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
7- What are your thoughts on religion? Is there an afterlife?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
30~ What's something unexpected that turns you on?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
1- What was your first impression of me? Has it changed?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
62~ Have you used adult toys?
4- For a pet, Cat, dog or other?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
If you win, what will you make them do?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How well do you know me? And some of your thoughts about me
Nothing too Serious
How old are you? Male or Female?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
18~ Who/when was your first “crush”?
13- What is the craziest/scariest thing you've ever done?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
*** Random Questions ***
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…
84~ How do you feel about reading/listening to adult stories?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Repairman/Lonely Wife Virgin/Experienced
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
80~ Share your top three fantasies/desires. (Be detailed) 😊
19~ Who/when was your first “heartbreak”?
29~ What are some things that turn you off? What is your biggest turn off?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Teacher/Student Stranger/One Night Stand
Do you shave/trim your pubic hair? For you guys do you shave your balls?
29- How superstitious are you?
26~ What side of the bed do you sleep on?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Does the thought excite you? Care to share?
Family Relation Age Play
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
11- List at least 5 things on your bucket list. Have you done any of them already?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
34~ Do you like the lights on or off during sex?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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 position? Why?
3- What’s your favorite smell? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
12- What’s your favorite food? What’s your least favorite?
52~ What are your hobbies?
50~ How many children do you have? What are their ages?
8- What are your thoughts on politics?
92~ Everyone needs a “safe” word. What is yours?
13- What’s your favorite drink? What’s your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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…
38~ Share your most embarrassing sexual memory?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Do you watch it? What is your favorite?
49~ How many times have you been married? Why did they end?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
25~ How do you feel about PDA? (Public Display of Affection)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Doctor/Nurse Stripper/Client
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
9~ How many times over your lifetime do you think you have had sex so far?
Would you read them together?
10- What is your favorite family tradition? What’s your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
76~ Have you had a threesome? Care to Share?
Any that are a turn off?
36~ What is your favorite time of day to have sex/make love?
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
31- If given a chance to be immortal, would you take it? Why?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
23- What is your dream job? What was it as a child?