What is the most interesting question you can ask to get to know someone?
Last Updated: 27.06.2025 22:29
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If NO, would you ever have one? Would it be with 2 men or 2 women?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
If there is an abandoned house with no owner, can I live in it?
If YES, was it with 2 men or 2 women? Did you enjoy it?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
19~ Who/when was your first “heartbreak”?
Prisoner/Prison Guard Landlord/Tenant
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
What nonsense did you hear today in India that made you laugh?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
28~ What are some things that turn on? What is your biggest turn on?
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23- What is your dream job? What was it as a child?
61~ How willing would you be to try new sexual positions?
How old are you? Male or Female?
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26~ What side of the bed do you sleep on?
14- What is an embarrassing moment in your life? How about your most embarrassing?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
11- List at least 5 things on your bucket list. Have you done any of them already?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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80~ Share your top three fantasies/desires. (Be detailed) 😊
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would Taylor Swift want to be as rich as Trump? This why she vote for Kamala?
Do you like the “69” position? Do you prefer to be on top or bottom?
Over time has your thoughts on sex changed?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What were the reasons for Stalin and Brezhnev's dislike of Khrushchev?
82~ Do you have any fantasies involving Role-Playing?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
The Ice Breaker Questions
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What is your favorite toy? Ever wanted to try a specific toy?
Doctor/Nurse Stripper/Client
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What are your controversial and hot takes on Naruto?
20- What’s your favorite candy? What’s your least favorite?
You know that I will be 100% truthful, so ask.
64~ When was your very first orgasm? When was your first from having sex? Care to share?
15~ Have you ever been “in love”? Who? Care to Share?
Do you think this brought you closer together?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What have you learned about me that was new and/or surprising?
8- What's your favorite flavor of ice cream? Do you a least favorite?
7- What are your thoughts on religion? Is there an afterlife?
Can you Deep Throat? Do you like the taste of yourself?
Please share Did you stop?
15- What's your favorite saying? What word or phrase is your least favorite?
50~ How many children do you have? What are their ages?
How well do you know me? And some of your thoughts about me
12- What’s your favorite food? What’s your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
I would allow you to do it… What would you do to me?
17- Have you ever done drugs? Which ones? How often?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would /have you ever given your partner a lap dance and Striptease?
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)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
52~ Are you willing to make “those types” of bets with your partner?
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?
13- What’s your favorite drink? What’s your least favorite?
21~ What was the best date you ever went on? What has been the worst?
81~ Do you have any kinks and/or fetishes?
28- What are some things that people do that irritate you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you watch it? What is your favorite?
10- What is your favorite family tradition? What’s your least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
*** Questions About Me ***
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
38~ Share your most embarrassing sexual memory?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
9- What’s your favorite season and why? What’s your least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
24~ What are your expectations in a relationship? (I know a very big question, take your time)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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,
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
If you say it, I will stop, and we can talk about it when you are ready.
9~ How many times over your lifetime do you think you have had sex so far?
84~ How do you feel about reading/listening to adult stories?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
13- How about having a certain hair cut/style?
11- What's your favorite restaurant? What’s your least favorite?
8- What are your thoughts on politics?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Have you ever? Care to Share?
If you win, what will you make them do?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
10~ How many dates are necessary before you to have sex with someone?
Escort/Client Job Applicant/Hiring Manager
11~ Have you ever been caught by your parents or children or others while having sex?
21- What's your favorite way to spend a weekend or time off?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
48~ Do you have any siblings? Are you close to your family?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How about if they talk dirty and/or call you names?
How many partners have you had oral sex with? Who? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Any that are a turn off?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
89~ Do you like taking showers together?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
3- What Superhero or Superpower would you want to be/have?
2- What’s your favorite color? Do you a least favorite?
Would you mind if your partner watched it? How about together vs alone?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
29~ What are some things that turn you off? What is your biggest turn off?
Do you have a favorite? Is it ok if your partner does?
42~ What’s your biggest regret in life?
92~ Everyone needs a “safe” word. What is yours?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
39~ What are your love languages?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
14- What's your favorite dessert? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
34~ Do you like the lights on or off during sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
4- For a pet, Cat, dog or other?
Nurse/Patient Celebrity/Fan
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Teacher/Student Stranger/One Night Stand
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
33- Beach or Mountains? Or is there another place to like better?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Would you ever want to be woken up with oral and/or intercourse?
7- What if a person smells a certain way? 8- How about smoking?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
83~ How do you feel about Porn?
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…
62~ Have you used adult toys?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
13~ Is there a difference between, making love, having sex, and fucking?
Would you read them together?
Does the thought excite you? Care to share?
1~ How old were you when you had your first kiss? Who? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- If you could have three wishes, what would they be? Why?
How many times do you think you have “made love”?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
92~ Have you ever had or have an STD? How many? What was it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** Random Questions ***
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
*** Deal Breaker Questions ***
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Family Relation Age Play
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
11- How about if they like a certain sports team? 12-How about drinking too much?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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…
What have you learned about yourself that you did not before this?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Any that are a turn off?
*** Questions about Relationships/Past ***
17- What’s your favorite holiday? What’s your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
18~ Who/when was your first “crush”?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
12- What is the weirdest thing you've ever eaten?
76~ Have you had a threesome? Care to Share?
Nothing too Serious
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
48~ Have you ever paid or been paid for sex?
36~ What is your favorite time of day to have sex/make love?
36- Do you play video games? What is your favorite? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Do you like it when they show and tell you what they want?
49~ How many times have you been married? Why did they end?
Model/Photographer Police/Criminal
53~ How much can you tell me about the one thing you are most passionate about?
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?
31- If given a chance to be immortal, would you take it? Why?
51~ What tends to bring a smile to your face?
If yes, what?
37- Do you like your name? If you could change it, what would you change it too?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
1- What was your first impression of me? Has it changed?
3- What’s your favorite smell? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
19- Do/have you smoked? What do you prefer? How often?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
22- What is your favorite childhood memory? What is your least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
47~ What would be your dream job and why?
30~ What's something unexpected that turns you on?
27- What was/ is nickname? Does it have a meaning behind it?
44~ Care to share something about yourself that no one else knows about you?
What is your view on sex? Meaning, When/Where/ How often/
What would you say to prove to yourself that it was really you?
34- Ever been to a concert? What was your favorite? Who would you like to see?
10- List 5 of your top pet peeves.
What do you dislike about me? I asked you to be 100% honest.
33- If you could visit any time period, when would you pick? Please explain why?
70~ Would/do you have/like anal sex?
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?
51~ Are you willing to play adult games with your partner?
40~ What’s the weirdest place you’ve ever had sex?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
* Give a rating for each one (0-100)
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you do it again, and would you rather 2 females or 2 males?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
29- How superstitious are you?
19- What’s your favorite fairytale? What’s your least favorite?
52~ What are your hobbies?
25~ How do you feel about PDA? (Public Display of Affection)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
60~ How important is oral sex? Do you like receiving? Do you like giving?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
9- Is there something you’ve always wanted to ask me but you’re afraid?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
6- Do you have dreams? Can you remember them? What do you usually dream about?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
*** What’s Your Favorite…? ***
Repairman/Lonely Wife Virgin/Experienced
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
That one or two things that made you go hmmmm, OMG or wow!
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
Will you cheat again? How can, you be sure? Define what cheating is to you.
13- What is the craziest/scariest thing you've ever done?
5~ When you first started having sex, was it what you thought it would be?
32- What's your greatest talent? Can I see it right now?
Master/Slave Boss/Maid
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What is your favorite position? Why?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
65~ Describe the best orgasm you’ve ever had? Care to share?