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