What is the most interesting question you can ask to get to know someone?
14.06.2025 07:03
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…
Please share Did you stop?
29- How superstitious are you?
Research suggests Big Bang may have taken place inside a black hole - Hacker News
You know that I will be 100% truthful, so ask.
50~ How many children do you have? What are their ages?
Have you ever? Care to Share?
Who was the actor least deserving of an Academy Award?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
22- Do you have any birth marks? How about scars? Care to share how you got them?
How do you find out who your handler is as a targeted individual?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
9- If you could have three wishes, what would they be? Why?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Who are the archers in Genesis 49:23?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Would you do it again, and would you rather 2 females or 2 males?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
5- Have you ever been hypnotized? Would you allow yourself to be?
What's the most sordid activity you've ever seen or heard about at a bachelorette party?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
89~ Do you like taking showers together?
34~ Do you like the lights on or off during sex?
What's it like to have an IQ of 140 to 170? Do people notice you're different?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What is your favorite toy? Ever wanted to try a specific toy?
Model/Photographer Police/Criminal
These glowing axolotls may hold the secret to human limb regeneration - The Washington Post
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
42~ What’s your biggest regret in life?
33- Beach or Mountains? Or is there another place to like better?
In what ways Indian parents are destroying their children's life?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
48~ Do you have any siblings? Are you close to your family?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
32- What's your greatest talent? Can I see it right now?
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)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
71~ Would you give your partner a hand or foot job? Would you receive one?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
*** Random Questions ***
67~ Do you like it when your partner moans and/or is vocal during sex?
13- What’s your favorite drink? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
*** Deal Breaker Questions ***
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
39~ What are your love languages?
What have you learned about yourself that you did not before this?
25~ How do you feel about PDA? (Public Display of Affection)
34- Ever been to a concert? What was your favorite? Who would you like to see?
1- What’s your favorite animal? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
65~ Describe the best orgasm you’ve ever had? Care to share?
51~ What tends to bring a smile to your face?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
11- How about if they like a certain sports team? 12-How about drinking too much?
18- How often do you drink alcohol? What is your favorite drink?
*** What’s Your Favorite…? ***
2- What’s your favorite color? Do you a least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
49~ How many times have you been married? Why did they end?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1~ How old were you when you had your first kiss? Who? Care to Share?
30~ What's something unexpected that turns you on?
11~ Have you ever been caught by your parents or children or others while having sex?
How well do you know me? And some of your thoughts about me
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What is your view on sex? Meaning, When/Where/ How often/
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
36- Do you play video games? What is your favorite? Do you a least favorite?
What have you learned about me that was new and/or surprising?
9~ How many times over your lifetime do you think you have had sex so far?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
10- What is your favorite family tradition? What’s your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
40~ What’s the weirdest place you’ve ever had sex?
92~ Have you ever had or have an STD? How many? What was it?
I would allow you to do it… What would you do to me?
20- What’s your favorite candy? What’s your least favorite?
1- What was your first impression of me? Has it changed?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
Family Relation Age Play
38~ Share your most embarrassing sexual memory?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
61~ How willing would you be to try new sexual positions?
80~ Share your top three fantasies/desires. (Be detailed) 😊
8- What's your favorite flavor of ice cream? Do you a least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
28- What are some things that people do that irritate you?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Repairman/Lonely Wife Virgin/Experienced
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you like it when they show and tell you what they want?
51~ Are you willing to play adult games with your partner?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
7- What if a person smells a certain way? 8- How about smoking?
Over time has your thoughts on sex changed?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Can you Deep Throat? Do you like the taste of yourself?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
81~ Do you have any kinks and/or fetishes?
19- What’s your favorite fairytale? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Nurse/Patient Celebrity/Fan
Do you have a favorite? Is it ok if your partner does?
If you say it, I will stop, and we can talk about it when you are ready.
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?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
62~ Have you used adult toys?
92~ Everyone needs a “safe” word. What is yours?
Get this wrong and this could mean the end… :-) some funny, some not…
Would you mind if your partner watched it? How about together vs alone?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Teacher/Student Stranger/One Night Stand
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
36~ What is your favorite time of day to have sex/make love?
(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…)
22- What is your favorite childhood memory? What is your least favorite?
26~ What side of the bed do you sleep on?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What do you dislike about me? I asked you to be 100% honest.
19- Do/have you smoked? What do you prefer? How often?
13- How about having a certain hair cut/style?
3- What Superhero or Superpower would you want to be/have?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Would you ever want to be woken up with oral and/or intercourse?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
What was the longest? What was the shortest?
Does the thought excite you? Care to share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
How old are you? Male or Female?
How about if they talk dirty and/or call you names?
19~ Who/when was your first “heartbreak”?
13- What is the craziest/scariest thing you've ever done?
Would you allow me to clean every part of your body with my soapy hands and fingers?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
84~ How do you feel about reading/listening to adult stories?
4- For a pet, Cat, dog or other?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
How many partners have you had oral sex with? Who? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? 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,
3- What’s your favorite smell? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
7-What do I do in bed that drives you wild? How about, what turns you off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
3- Should Pluto still be considered a planet? 4- How about smoking?
14- What's your favorite dessert? Do you a least favorite?
44~ Care to share something about yourself that no one else knows about you?
If you win, what will you make them do?
5~ When you first started having sex, was it what you thought it would be?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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?
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…
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What is your favorite position? Why?
The Ice Breaker Questions
*** Questions about Relationships/Past ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
76~ Have you had a threesome? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
47~ What would be your dream job and why?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
12- What is the weirdest thing you've ever eaten?
Escort/Client Job Applicant/Hiring Manager
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
52~ Are you willing to make “those types” of bets with your partner?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Do you watch it? What is your favorite?
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~ Have you ever been “in love”? Who? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
11- What's your favorite restaurant? What’s your least favorite?
8- What are your thoughts on politics?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
23- What is your dream job? What was it as a child?
Any that are a turn off?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
52~ What are your hobbies?
That one or two things that made you go hmmmm, OMG or wow!
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
If yes, what?
7- What are your thoughts on religion? Is there an afterlife?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
10- List 5 of your top pet peeves.
9- Is there something you’ve always wanted to ask me but you’re afraid?
Do you like the “69” position? Do you prefer to be on top or bottom?
82~ Do you have any fantasies involving Role-Playing?
28~ What are some things that turn on? What is your biggest turn on?
Would /have you ever given your partner a lap dance and Striptease?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What would you say to prove to yourself that it was really you?
15- What bad habit do you wish you could quit? Do you have any addictions?
Any that are a turn off?
Nothing too Serious
15- What's your favorite saying? What word or phrase is your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
83~ How do you feel about Porn?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Master/Slave Boss/Maid
Doctor/Nurse Stripper/Client
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
53~ How much can you tell me about the one thing you are most passionate about?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
* Give a rating for each one (0-100)
17- Have you ever done drugs? Which ones? How often?
21- What's your favorite way to spend a weekend or time off?
10~ How many dates are necessary before you to have sex with someone?
31- If given a chance to be immortal, would you take it? Why?
Would you read them together?
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?
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?
How many times do you think you have “made love”?
14- What is an embarrassing moment in your life? How about your most embarrassing?
12- What’s your favorite food? What’s your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
21~ What was the best date you ever went on? What has been the worst?
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you think this brought you closer together?
37- Do you like your name? If you could change it, what would you change it too?
*** Questions About Me ***
9- What’s your favorite season and why? What’s your least favorite?
Prisoner/Prison Guard Landlord/Tenant
If NO, would you ever have one? Would it be with 2 men or 2 women?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
18~ Who/when was your first “crush”?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?