What is the most interesting question you can ask to get to know someone?
12.06.2025 00:27
17- What’s your favorite holiday? What’s your 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,
Master/Slave Boss/Maid
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
62~ Have you used adult toys?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? 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?
10- What is your favorite family tradition? What’s your least favorite?
Do you like it when they show and tell you what they want?
China fast tracks rare earth export licences for European companies - Financial Times
11- How about if they like a certain sports team? 12-How about drinking too much?
11~ Have you ever been caught by your parents or children or others while having sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Will you cheat again? How can, you be sure? Define what cheating is to you.
*** Deal Breaker Questions ***
I'm pretty sure that my dog is transgender, how would I go about transitioning it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13- What’s your favorite drink? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Are Indian youths conservative or liberal?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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?
12- What is the weirdest thing you've ever eaten?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
28~ What are some things that turn on? What is your biggest turn on?
How does the narcissist react when he realizes you no longer care?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How can we become the best humans? How can we trust each other?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
92~ Everyone needs a “safe” word. What is yours?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
5~ When you first started having sex, was it what you thought it would be?
5- Have you ever been hypnotized? Would you allow yourself to be?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Do you remember one day, you put a deep smile on someone's face and made them very happy?
Please share Did you stop?
(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…)
9- What’s your favorite season and why? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
67~ Do you like it when your partner moans and/or is vocal during 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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
47~ What would be your dream job and why?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
53~ How much can you tell me about the one thing you are most passionate about?
13- How about having a certain hair cut/style?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Nurse/Patient Celebrity/Fan
45~ How do you feel about me blindfolding you? How about blindfolding me?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
27- What was/ is nickname? Does it have a meaning behind it?
33- If you could visit any time period, when would you pick? Please explain why?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
1- What was your first impression of me? Has it changed?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
11- What's your favorite restaurant? What’s your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Have you ever? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
If yes, what?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
40~ What’s the weirdest place you’ve ever had sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
The Ice Breaker Questions
34- Ever been to a concert? What was your favorite? Who would you like to see?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Any that are a turn off?
18- How often do you drink alcohol? What is your favorite drink?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
2- What’s your favorite color? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
48~ Do you have any siblings? Are you close to your family?
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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
* Give a rating for each one (0-100)
Teacher/Student Stranger/One Night Stand
70~ Would/do you have/like anal sex?
Family Relation Age Play
18~ Who/when was your first “crush”?
12- What’s your favorite food? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What have you learned about me that was new and/or surprising?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
14- What's your favorite dessert? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
*** What’s Your Favorite…? ***
1~ How old were you when you had your first kiss? Who? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
You know that I will be 100% truthful, so ask.
Any that are a turn off?
Would you mind if your partner watched it? How about together vs alone?
11- List at least 5 things on your bucket list. Have you done any of them already?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
I would allow you to do it… What would you do to me?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would you read them together?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
30~ What's something unexpected that turns you on?
52~ Are you willing to make “those types” of bets with your partner?
29- How superstitious are you?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
6- Do you have dreams? Can you remember them? What do you usually dream about?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
10~ How many dates are necessary before you to have sex with someone?
Nothing too Serious
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
3- Should Pluto still be considered a planet? 4- How about smoking?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
39~ What are your love languages?
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
61~ How willing would you be to try new sexual positions?
What is your favorite toy? Ever wanted to try a specific toy?
How about if they talk dirty and/or call you names?
51~ Are you willing to play adult games with your partner?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
34~ Do you like the lights on or off during sex?
21- What's your favorite way to spend a weekend or time off?
42~ What’s your biggest regret in life?
If NO, would you ever have one? Would it be with 2 men or 2 women?
19- What’s your favorite fairytale? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
13~ Is there a difference between, making love, having sex, and fucking?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
7- What if a person smells a certain way? 8- How about smoking?
How well do you know me? And some of your thoughts about me
Would you ever want to be woken up with oral and/or intercourse?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
9- If you could have three wishes, what would they be? Why?
What would you say to prove to yourself that it was really you?
25~ How do you feel about PDA? (Public Display of Affection)
32- What's your greatest talent? Can I see it right now?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
83~ How do you feel about Porn?
*** Random Questions ***
15- What's your favorite saying? What word or phrase is your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
31- If given a chance to be immortal, would you take it? Why?
Escort/Client Job Applicant/Hiring Manager
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
26~ What side of the bed do you sleep on?
Doctor/Nurse Stripper/Client
19- Do/have you smoked? What do you prefer? How often?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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?
17- Have you ever done drugs? Which ones? How often?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Can you Deep Throat? Do you like the taste of yourself?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
If you win, what will you make them do?
29~ What are some things that turn you off? What is your biggest turn off?
50~ How many children do you have? What are their ages?
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?
Prisoner/Prison Guard Landlord/Tenant
4- For a pet, Cat, dog or other?
92~ Have you ever had or have an STD? How many? What was it?
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?
7- What are your thoughts on religion? Is there an afterlife?
If you say it, I will stop, and we can talk about it when you are ready.
Do you watch it? What is your favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
89~ Do you like taking showers together?
How many partners have you had oral sex with? Who? Care to Share?
33- Beach or Mountains? Or is there another place to like better?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What is your view on sex? Meaning, When/Where/ How often/
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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…
36- Do you play video games? What is your favorite? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
71~ Would you give your partner a hand or foot job? Would you receive one?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
23- What is your dream job? What was it as a child?
How many times do you think you have “made love”?
38~ Share your most embarrassing sexual memory?
Do you like the “69” position? Do you prefer to be on top or bottom?
65~ Describe the best orgasm you’ve ever had? Care to share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
3- What Superhero or Superpower would you want to be/have?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
9~ How many times over your lifetime do you think you have had sex so far?
What was the longest? What was the shortest?
That one or two things that made you go hmmmm, OMG or wow!
8- What's your favorite flavor of ice cream? Do you a least favorite?
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?
3- What’s your favorite smell? Do you a least favorite?
49~ How many times have you been married? Why did they end?
8- What are your thoughts on politics?
How old are you? Male or Female?
15~ Have you ever been “in love”? Who? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
76~ Have you had a threesome? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
82~ Do you have any fantasies involving Role-Playing?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you think this brought you closer together?
28- What are some things that people do that irritate you?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Model/Photographer Police/Criminal
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
14- What is an embarrassing moment in your life? How about your most embarrassing?
51~ What tends to bring a smile to your face?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
52~ What are your hobbies?
44~ Care to share something about yourself that no one else knows about you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
84~ How do you feel about reading/listening to adult stories?
Would you do it again, and would you rather 2 females or 2 males?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
10- List 5 of your top pet peeves.
41~ Are there moments in your past that you would want to change? Please share 3 of them.
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you have a favorite? Is it ok if your partner does?
What is your favorite position? Why?
80~ Share your top three fantasies/desires. (Be detailed) 😊
*** Questions about Relationships/Past ***
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Over time has your thoughts on sex changed?
37- Do you like your name? If you could change it, what would you change it too?
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)
What have you learned about yourself that you did not before this?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
13- What is the craziest/scariest thing you've ever done?
Does the thought excite you? Care to share?
What do you dislike about me? I asked you to be 100% honest.
22- What is your favorite childhood memory? What is your least favorite?
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…
19~ Who/when was your first “heartbreak”?
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?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
*** Questions About Me ***
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Repairman/Lonely Wife Virgin/Experienced
15- What bad habit do you wish you could quit? Do you have any addictions?
81~ Do you have any kinks and/or fetishes?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?