What is the most interesting question you can ask to get to know someone?
09.06.2025 23:53
9- What’s your favorite season and why? What’s your least favorite?
*** Random Questions ***
22- Do you have any birth marks? How about scars? Care to share how you got them?
Why do old men think young women and girls would want them over guys their own age?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What do you dislike about me? I asked you to be 100% honest.
52~ What are your hobbies?
How do I overcome attachment issues?
76~ Have you had a threesome? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
2- What’s your favorite color? Do you a least favorite?
Why have Indian girls almost stopped wearing sarees?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
25~ How do you feel about PDA? (Public Display of Affection)
I would allow you to do it… What would you do to me?
My friend asked my crush and he said my crush hates me but not in a rude way. What does that mean?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Do you have a favorite? Is it ok if your partner does?
Get this wrong and this could mean the end… :-) some funny, some not…
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21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
33- If you could visit any time period, when would you pick? Please explain why?
51~ Are you willing to play adult games with your partner?
How do you recognize when your mental health might need attention?
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)
10~ How many dates are necessary before you to have sex with someone?
29- How superstitious are you?
Any that are a turn off?
44~ Care to share something about yourself that no one else knows about you?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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How well do you know me? And some of your thoughts about me
13- What is the craziest/scariest thing you've ever done?
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?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would you mind if your partner watched it? How about together vs alone?
Master/Slave Boss/Maid
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52~ Are you willing to make “those types” of bets with your partner?
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?
How do you leave a relationship when you are still in love?
67~ Do you like it when your partner moans and/or is vocal during sex?
14- What is an embarrassing moment in your life? How about your most embarrassing?
30~ What's something unexpected that turns you on?
Why do only ugly women like me on Tinder? Is it because I'm an ugly man?
21- What's your favorite way to spend a weekend or time off?
17- What’s your favorite holiday? What’s your least favorite?
38~ Share your most embarrassing sexual memory?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Do you watch it? What is your favorite?
19- Do/have you smoked? What do you prefer? How often?
What is the difference between the Bible and the Qur'an?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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…
71~ Would you give your partner a hand or foot job? Would you receive one?
7- What are your thoughts on religion? Is there an afterlife?
11~ Have you ever been caught by your parents or children or others while having sex?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
1- What was your first impression of me? Has it changed?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
20- What’s your favorite candy? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
32- What's your greatest talent? Can I see it right now?
36~ What is your favorite time of day to have sex/make love?
15~ Have you ever been “in love”? Who? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
18~ Who/when was your first “crush”?
39~ What are your love languages?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you think this brought you closer together?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
29~ What are some things that turn you off? What is your biggest turn off?
81~ Do you have any kinks and/or fetishes?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
4- For a pet, Cat, dog or other?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
47~ What would be your dream job and why?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
The Ice Breaker Questions
51~ What tends to bring a smile to your face?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you like it when they show and tell you what they want?
22- What is your favorite childhood memory? What is your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? 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?
Would you read them together?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
53~ How much can you tell me about the one thing you are most passionate about?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
19- What’s your favorite fairytale? What’s your least favorite?
82~ Do you have any fantasies involving Role-Playing?
60~ How important is oral sex? Do you like receiving? Do you like giving?
*** Deal Breaker Questions ***
Would you do it again, and would you rather 2 females or 2 males?
28~ What are some things that turn on? What is your biggest turn on?
Family Relation Age Play
92~ Have you ever had or have an STD? How many? What was it?
*** What’s Your 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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
92~ Everyone needs a “safe” word. What is yours?
*** Questions about Relationships/Past ***
7- What if a person smells a certain way? 8- How about smoking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
48~ Have you ever paid or been paid for sex?
If yes, what?
37- Do you like your name? If you could change it, what would you change it too?
3- What Superhero or Superpower would you want to be/have?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
You know that I will be 100% truthful, so ask.
11- List at least 5 things on your bucket list. Have you done any of them already?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
10- What is your favorite family tradition? What’s your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What was the longest? What was the shortest?
1~ How old were you when you had your first kiss? Who? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
How many times do you think you have “made love”?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
What would you say to prove to yourself that it was really you?
*** Questions About Me ***
Teacher/Student Stranger/One Night Stand
10- List 5 of your top pet peeves.
What is your view on sex? Meaning, When/Where/ How often/
89~ Do you like taking showers together?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
48~ Do you have any siblings? Are you close to your family?
50~ How many children do you have? What are their ages?
7-What do I do in bed that drives you wild? How about, what turns you off?
83~ How do you feel about Porn?
Would you allow me to clean every part of your body with my soapy hands and fingers?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What is your favorite position? Why?
9- If you could have three wishes, what would they be? Why?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
15- What's your favorite saying? What word or phrase is your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
14- What's your favorite dessert? Do you a least favorite?
49~ How many times have you been married? Why did they end?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
13- How about having a certain hair cut/style?
Any that are a turn off?
34- Ever been to a concert? What was your favorite? Who would you like to see?
If you say it, I will stop, and we can talk about it when you are ready.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
70~ Would/do you have/like anal sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
How old are you? Male or Female?
That one or two things that made you go hmmmm, OMG or wow!
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?
Would /have you ever given your partner a lap dance and Striptease?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Would you ever want to be woken up with oral and/or intercourse?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
27- What was/ is nickname? Does it have a meaning behind it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
26~ What side of the bed do you sleep on?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Model/Photographer Police/Criminal
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
40~ What’s the weirdest place you’ve ever had sex?
9~ How many times over your lifetime do you think you have had sex so far?
What is your favorite toy? Ever wanted to try a specific toy?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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?
* Give a rating for each one (0-100)
13~ Is there a difference between, making love, having sex, and fucking?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
18- How often do you drink alcohol? What is your favorite drink?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
36- Do you play video games? What is your favorite? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
12- What is the weirdest thing you've ever eaten?
Escort/Client Job Applicant/Hiring Manager
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Have you ever? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What have you learned about yourself that you did not before this?
Please share Did you stop?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
How many partners have you had oral sex with? Who? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
Nothing too Serious
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you like the “69” position? Do you prefer to be on top or bottom?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
34~ Do you like the lights on or off during sex?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
28- What are some things that people do that irritate you?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
9- Is there something you’ve always wanted to ask me but you’re afraid?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
3- Should Pluto still be considered a planet? 4- How about smoking?
Can you Deep Throat? Do you like the taste of yourself?
Doctor/Nurse Stripper/Client
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What have you learned about me that was new and/or surprising?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
5- Have you ever been hypnotized? Would you allow yourself to be?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Will you cheat again? How can, you be sure? Define what cheating is to you.
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
19~ Who/when was your first “heartbreak”?
Repairman/Lonely Wife Virgin/Experienced
Over time has your thoughts on sex changed?
15- What bad habit do you wish you could quit? Do you have any addictions?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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,
62~ Have you used adult toys?
8- What are your thoughts on politics?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If you win, what will you make them do?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
23- What is your dream job? What was it as a child?
Prisoner/Prison Guard Landlord/Tenant
How about if they talk dirty and/or call you names?
3- What’s your favorite smell? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
Nurse/Patient Celebrity/Fan
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?
1- What’s your favorite animal? Do you a least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
(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…)
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
84~ How do you feel about reading/listening to adult stories?
17- Have you ever done drugs? Which ones? How often?
45~ How do you feel about me blindfolding you? How about blindfolding me?
31- If given a chance to be immortal, would you take it? Why?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
42~ What’s your biggest regret in life?
6- Do you have dreams? Can you remember them? What do you usually dream about?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
61~ How willing would you be to try new sexual positions?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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- What’s your favorite food? What’s your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)