What is the most interesting question you can ask to get to know someone?
14.06.2025 06:27
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
51~ Are you willing to play adult games with your partner?
19~ Who/when was your first “heartbreak”?
Have you been with a stranger yet?
21~ What was the best date you ever went on? What has been the worst?
How many times do you think you have “made love”?
18- How often do you drink alcohol? What is your favorite drink?
Is heroin really as good as people say it is?
5- Have you ever been hypnotized? Would you allow yourself to be?
47~ What would be your dream job and why?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Why do narcissists devour so much sugar (candy, ice cream, donuts, etc., in huge amounts at a time)?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
19- What’s your favorite fairytale? What’s your least favorite?
9- If you could have three wishes, what would they be? Why?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
10- List 5 of your top pet peeves.
Over time has your thoughts on sex changed?
14- What is an embarrassing moment in your life? How about your most embarrassing?
37- Do you like your name? If you could change it, what would you change it too?
We've Been Misreading a Major Law of Physics For Nearly 300 Years - ScienceAlert
Would you read them together?
Any that are a turn off?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What do people aim for when they meditate, and how do they do it properly?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What do you dislike about me? I asked you to be 100% honest.
19- Do/have you smoked? What do you prefer? How often?
How does someone start doing urban exploration?
44~ Care to share something about yourself that no one else knows about you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
As a woman, what would be you response to a male friend’s offer of a full body massage?
Any that are a turn off?
10~ How many dates are necessary before you to have sex with someone?
Model/Photographer Police/Criminal
Is LGBTQ destroying the world?
11- How about if they like a certain sports team? 12-How about drinking too much?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
17- Have you ever done drugs? Which ones? How often?
What is the Replika app, and how does it work?
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?
51~ What tends to bring a smile to your face?
40~ What’s the weirdest place you’ve ever had sex?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Can you share 100 facts about yourself?
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?
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?
Do leftists understand why young men are becoming more right-wing?
What is your favorite toy? Ever wanted to try a specific toy?
Would you ever want to be woken up with oral and/or intercourse?
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)
12- What is the weirdest thing you've ever eaten?
14- What's your favorite dessert? Do you a least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
42~ What’s your biggest regret in life?
52~ Are you willing to make “those types” of bets with your partner?
7- What if a person smells a certain way? 8- How about smoking?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Family Relation Age Play
65~ Describe the best orgasm you’ve ever had? 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,
21- What's your favorite way to spend a weekend or time off?
70~ Would/do you have/like anal sex?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Can you Deep Throat? Do you like the taste of yourself?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
27- What was/ is nickname? Does it have a meaning behind it?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
The Ice Breaker Questions
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
62~ Have you used adult toys?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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?
28- What are some things that people do that irritate you?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Prisoner/Prison Guard Landlord/Tenant
Will you cheat again? How can, you be sure? Define what cheating is to you.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
61~ How willing would you be to try new sexual positions?
22- What is your favorite childhood memory? What is your least favorite?
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…
89~ Do you like taking showers together?
25~ How do you feel about PDA? (Public Display of Affection)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What is your view on sex? Meaning, When/Where/ How often/
84~ How do you feel about reading/listening to adult stories?
28~ What are some things that turn on? What is your biggest turn on?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
13- What’s your favorite drink? What’s your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you like the “69” position? Do you prefer to be on top or bottom?
15~ Have you ever been “in love”? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Does the thought excite you? Care to share?
33- If you could visit any time period, when would you pick? Please explain why?
*** Questions about Relationships/Past ***
Would you mind if your partner watched it? How about together vs alone?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
39~ What are your love languages?
82~ Do you have any fantasies involving Role-Playing?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
92~ Everyone needs a “safe” word. What is yours?
10- What is your favorite family tradition? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
How many partners have you had oral sex with? Who? Care to Share?
Teacher/Student Stranger/One Night Stand
3- What’s your favorite smell? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
49~ How many times have you been married? Why did they end?
17- What’s your favorite holiday? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
36~ What is your favorite time of day to have sex/make love?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
29- How superstitious are you?
That one or two things that made you go hmmmm, OMG or wow!
*** Random Questions ***
32- What's your greatest talent? Can I see it right now?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
18~ Who/when was your first “crush”?
9- What’s your favorite season and why? What’s your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
How old are you? Male or Female?
50~ How many children do you have? What are their ages?
11~ Have you ever been caught by your parents or children or others while having sex?
53~ How much can you tell me about the one thing you are most passionate about?
20- What’s your favorite candy? What’s your least favorite?
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?
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- What is the craziest/scariest thing you've ever done?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
2- What’s your favorite color? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Do you have a favorite? Is it ok if your partner does?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
33- Beach or Mountains? Or is there another place to like better?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What would you say to prove to yourself that it was really you?
7- What are your thoughts on religion? Is there an afterlife?
Get this wrong and this could mean the end… :-) some funny, some not…
15- What's your favorite saying? What word or phrase is your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
30~ What's something unexpected that turns you on?
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 you say it, I will stop, and we can talk about it when you are ready.
83~ How do you feel about Porn?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would you do it again, and would you rather 2 females or 2 males?
13~ Is there a difference between, making love, having sex, and fucking?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
4- For a pet, Cat, dog or other?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Nurse/Patient Celebrity/Fan
48~ Do you have any siblings? Are you close to your family?
Please share Did you stop?
*** Questions About Me ***
31- If given a chance to be immortal, would you take it? Why?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
What have you learned about yourself that you did not before this?
23- What is your dream job? What was it as a child?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
What have you learned about me that was new and/or surprising?
*** Deal Breaker Questions ***
52~ What are your hobbies?
8- What are your thoughts on politics?
You know that I will be 100% truthful, so ask.
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?
Nothing too Serious
5~ When you first started having sex, was it what you thought it would be?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
38~ Share your most embarrassing sexual memory?
81~ Do you have any kinks and/or fetishes?
*** What’s Your Favorite…? ***
Do you like it when they show and tell you what they want?
92~ Have you ever had or have an STD? How many? What was it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
1~ How old were you when you had your first kiss? 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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How about if they talk dirty and/or call you names?
12- What’s your favorite food? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
34~ Do you like the lights on or off during sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Repairman/Lonely Wife Virgin/Experienced
60~ How important is oral sex? Do you like receiving? Do you like giving?
What was the longest? What was the shortest?
26~ What side of the bed do you sleep on?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Do you watch it? What is your favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
76~ Have you had a threesome? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
13- How about having a certain hair cut/style?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
34- Ever been to a concert? What was your favorite? Who would you like to see?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
(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…)
15- What bad habit do you wish you could quit? Do you have any addictions?
48~ Have you ever paid or been paid for sex?
If you win, what will you make them do?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
If yes, what?
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?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
11- List at least 5 things on your bucket list. Have you done any of them already?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would /have you ever given your partner a lap dance and Striptease?
3- What Superhero or Superpower would you want to be/have?
22- Do you have any birth marks? How about scars? Care to share how you got them?
11- What's your favorite restaurant? What’s your least favorite?
* Give a rating for each one (0-100)
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What is your favorite position? Why?
Doctor/Nurse Stripper/Client
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Do you think this brought you closer together?
I would allow you to do it… What would you do to me?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
29~ What are some things that turn you off? What is your biggest turn off?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Master/Slave Boss/Maid
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
1- What was your first impression of me? Has it changed?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
80~ Share your top three fantasies/desires. (Be detailed) 😊
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How well do you know me? And some of your thoughts about me
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Have you ever? Care to Share?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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…