What is the most interesting question you can ask to get to know someone?
16.06.2025 01:02
Would you do it again, and would you rather 2 females or 2 males?
1~ How old were you when you had your first kiss? Who? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What do you think of Tesla's Model Y coming in ninth among electric cars sales in Europe?
12- What is the weirdest thing you've ever eaten?
15- What's your favorite saying? What word or phrase is your least favorite?
12- What’s your favorite food? What’s your least favorite?
How is a narcissist likely to handle situations when confronted with hard truths about themselves?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What is your favorite toy? Ever wanted to try a specific toy?
How well do you know me? And some of your thoughts about me
Has anyone tried bestiality and been caught?
70~ Would/do you have/like anal sex?
Do you like it when they show and tell you what they want?
3- What’s your favorite smell? Do you a least favorite?
Where and how did ballet originate?
30~ What's something unexpected that turns you on?
15- What bad habit do you wish you could quit? Do you have any addictions?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
39~ What are your love languages?
9~ How many times over your lifetime do you think you have had sex so far?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Is the Las Vegas Grand Prix considered one of the "premier events on the Formula 1 calendar?"
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)
37- Do you like your name? If you could change it, what would you change it too?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How do you leave a relationship when you are still in love?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
48~ Have you ever paid or been paid for sex?
*** Questions about Relationships/Past ***
5- Have you ever been hypnotized? Would you allow yourself to be?
Take the short quiz here @ Discover Your Love Language® - The 5 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?
Model/Photographer Police/Criminal
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
That one or two things that made you go hmmmm, OMG or wow!
Why do I feel sleepy after massage?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
83~ How do you feel about Porn?
13~ Is there a difference between, making love, having sex, and fucking?
Why can't we send flat Earthers to space and show them the shape of Earth?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How do flat earthers explain the Earth being stationary? Is this concept considered impossible?
What do you dislike about me? I asked you to be 100% honest.
15~ Have you ever been “in love”? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Are LGBT people accepted in Japan?
81~ Do you have any kinks and/or fetishes?
Prisoner/Prison Guard Landlord/Tenant
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Why was Nietzsche against essentialism?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would you ever want to be woken up with oral and/or intercourse?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
76~ Have you had a threesome? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
7~ How many times in one day have you had sex? Who/When/Where? 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?
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?
Repairman/Lonely Wife Virgin/Experienced
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
If NO, would you ever have one? Would it be with 2 men or 2 women?
14- What's your favorite dessert? Do you a least favorite?
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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Any that are a turn off?
You know that I will be 100% truthful, so ask.
11- What's your favorite restaurant? What’s your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Over time has your thoughts on sex changed?
What would you say to prove to yourself that it was really you?
51~ What tends to bring a smile to your face?
Nothing too Serious
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
10~ How many dates are necessary before you to have sex with someone?
10- List 5 of your top pet peeves.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
50~ How many children do you have? What are their ages?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Do you watch it? What is your favorite?
51~ Are you willing to play adult games with your partner?
19- What’s your favorite fairytale? What’s your least favorite?
What is your favorite position? Why?
Please share Did you stop?
38~ Share your most embarrassing sexual memory?
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?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
22- Do you have any birth marks? How about scars? Care to share how you got them?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
67~ Do you like it when your partner moans and/or is vocal during sex?
48~ Do you have any siblings? Are you close to your family?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
(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…)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
8- What are your thoughts on politics?
31- If given a chance to be immortal, would you take it? Why?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
Would you mind if your partner watched it? How about together vs alone?
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
44~ Care to share something about yourself that no one else knows about you?
2- What’s your favorite color? Do you a least favorite?
What have you learned about yourself that you did not before this?
34- Ever been to a concert? What was your favorite? Who would you like to see?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Family Relation Age Play
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
28- What are some things that people do that irritate you?
3- What Superhero or Superpower would you want to be/have?
52~ Are you willing to make “those types” of bets with your partner?
36- Do you play video games? What is your favorite? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
13- How about having a certain hair cut/style?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
71~ Would you give your partner a hand or foot job? Would you receive one?
92~ Everyone needs a “safe” word. What is yours?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
21- What's your favorite way to spend a weekend or time off?
19- Do/have you smoked? What do you prefer? How often?
29~ What are some things that turn you off? What is your biggest turn off?
13- What’s your favorite drink? What’s your least favorite?
1- What was your first impression of me? Has it changed?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
The Ice Breaker Questions
11~ Have you ever been caught by your parents or children or others while having sex?
Would you read them together?
How many times do you think you have “made love”?
Nurse/Patient Celebrity/Fan
6- Do you have dreams? Can you remember them? What do you usually dream about?
89~ Do you like taking showers together?
If yes, what?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
53~ How much can you tell me about the one thing you are most passionate about?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What was the longest? What was the shortest?
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?
5~ When you first started having sex, was it what you thought it would be?
Does the thought excite you? Care to share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
62~ Have you used adult toys?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
20- What’s your favorite candy? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
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?
10- What is your favorite family tradition? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you like the “69” position? Do you prefer to be on top or bottom?
19~ Who/when was your first “heartbreak”?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
61~ How willing would you be to try new sexual positions?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
22- What is your favorite childhood memory? What is your least favorite?
9- If you could have three wishes, what would they be? Why?
25~ How do you feel about PDA? (Public Display of Affection)
*** Deal Breaker Questions ***
17- What’s your favorite holiday? What’s your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
What is your view on sex? Meaning, When/Where/ How often/
If you win, what will you make them do?
Do you have a favorite? Is it ok if your partner does?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
47~ What would be your dream job and why?
34~ Do you like the lights on or off during sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
32- What's your greatest talent? Can I see it right now?
17- Have you ever done drugs? Which ones? How often?
42~ What’s your biggest regret in life?
How many partners have you had oral sex with? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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,
Do you shave/trim your pubic hair? For you guys do you shave your balls?
49~ How many times have you been married? Why did they end?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
13- What is the craziest/scariest thing you've ever done?
60~ How important is oral sex? Do you like receiving? Do you like giving?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
18- How often do you drink alcohol? What is your favorite drink?
What have you learned about me that was new and/or surprising?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
* Give a rating for each one (0-100)
Master/Slave Boss/Maid
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How old are you? Male or Female?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
29- How superstitious are you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
33- Beach or Mountains? Or is there another place to like better?
If YES, was it with 2 men or 2 women? Did you enjoy it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
*** Questions About Me ***
8- What's your favorite flavor of ice cream? Do you a 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…
4- For a pet, Cat, dog or other?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
*** Random Questions ***
Would /have you ever given your partner a lap dance and Striptease?
80~ Share your top three fantasies/desires. (Be detailed) 😊
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
9- What’s your favorite season and why? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
7- What are your thoughts on religion? Is there an afterlife?
Will you cheat again? How can, you be sure? Define what cheating is to you.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Any that are a turn off?
40~ What’s the weirdest place you’ve ever had sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
I would allow you to do it… What would you do to me?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
82~ Do you have any fantasies involving Role-Playing?
Doctor/Nurse Stripper/Client
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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…
Do you think this brought you closer together?
*** What’s Your Favorite…? ***
46~ Have you ever used furniture, or other types of things to aid you while having sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
How about if they talk dirty and/or call you names?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
23- What is your dream job? What was it as a child?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Can you Deep Throat? Do you like the taste of yourself?
7- What if a person smells a certain way? 8- How about smoking?
26~ What side of the bed do you sleep on?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
52~ What are your hobbies?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
18~ Who/when was your first “crush”?
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Escort/Client Job Applicant/Hiring Manager
If you say it, I will stop, and we can talk about it when you are ready.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
21~ What was the best date you ever went on? What has been the worst?
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?