What is the most interesting question you can ask to get to know someone?
08.06.2025 06:21
19- What’s your favorite fairytale? What’s your least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How about if they talk dirty and/or call you names?
Any that are a turn off?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Model/Photographer Police/Criminal
He said he loves me, but why is it difficult for him to leave his wife?
8- What's your favorite flavor of ice cream? Do you a least favorite?
61~ How willing would you be to try new sexual positions?
7- What if a person smells a certain way? 8- How about smoking?
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68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would /have you ever given your partner a lap dance and Striptease?
The Ice Breaker Questions
Escort/Client Job Applicant/Hiring Manager
84~ How do you feel about reading/listening to adult stories?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What would happen if Kakashi and Naruto switched places?
9- If you could have three wishes, what would they be? Why?
9~ How many times over your lifetime do you think you have had sex so far?
38~ Share your most embarrassing sexual memory?
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?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
67~ Do you like it when your partner moans and/or is vocal during sex?
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20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
10- List 5 of your top pet peeves.
Earth's atmosphere hasn't had this much CO2 in millions of years - NBC News
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Please share Did you stop?
11- How about if they like a certain sports team? 12-How about drinking too much?
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58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
How many partners have you had oral sex with? Who? Care to Share?
What are some downsides to living in Newfoundland and Labrador (besides the weather)?
Would you mind if your partner watched it? How about together vs alone?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
29~ What are some things that turn you off? What is your biggest turn off?
What was the longest? What was the shortest?
Why do the majority of feminists hate men (not all feminists)?
26~ What side of the bed do you sleep on?
30~ What's something unexpected that turns you on?
If yes, what?
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
40~ What’s the weirdest place you’ve ever had sex?
What were your fantasies when you reached puberty?
7- What are your thoughts on religion? Is there an afterlife?
19~ Who/when was your first “heartbreak”?
Any that are a turn off?
Teacher/Student Stranger/One Night Stand
17- What’s your favorite holiday? What’s your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
28- What are some things that people do that irritate you?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
50~ How many children do you have? What are their ages?
*** Deal Breaker Questions ***
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
Master/Slave Boss/Maid
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
71~ Would you give your partner a hand or foot job? Would you receive one?
83~ How do you feel about Porn?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
19- Do/have you smoked? What do you prefer? How often?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
13- What is the craziest/scariest thing you've ever done?
3- What’s your favorite smell? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
62~ Have you used adult toys?
*** Questions about Relationships/Past ***
82~ Do you have any fantasies involving Role-Playing?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
I would allow you to do it… What would you do to me?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
65~ Describe the best orgasm you’ve ever had? Care to share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
10~ How many dates are necessary before you to have sex with someone?
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?
18~ Who/when was your first “crush”?
Would you do it again, and would you rather 2 females or 2 males?
47~ What would be your dream job and why?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
33- Beach or Mountains? Or is there another place to like better?
48~ Do you have any siblings? Are you close to your family?
92~ Have you ever had or have an STD? How many? What was it?
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,
23- What is your dream job? What was it as a child?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
Do you have a favorite? Is it ok if your partner does?
25~ How do you feel about PDA? (Public Display of Affection)
What is your view on sex? Meaning, When/Where/ How often/
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?
Have you ever? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Doctor/Nurse Stripper/Client
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
13- How about having a certain hair cut/style?
How old are you? Male or Female?
3- What Superhero or Superpower would you want to be/have?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
76~ Have you had a threesome? 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.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Would you allow me to clean every part of your body with my soapy hands and fingers?
48~ Have you ever paid or been paid for sex?
11~ Have you ever been caught by your parents or children or others while having sex?
15~ Have you ever been “in love”? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What would you say to prove to yourself that it was really you?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
52~ Are you willing to make “those types” of bets with your partner?
* 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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you watch it? What is your favorite?
You know that I will be 100% truthful, so ask.
44~ Care to share something about yourself that no one else knows about you?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Do you think this brought you closer together?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
92~ Everyone needs a “safe” word. What is yours?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
36- Do you play video games? What is your favorite? Do you a least favorite?
Over time has your thoughts on sex changed?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
34~ Do you like the lights on or off during sex?
9- What’s your favorite season and why? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
1- What’s your favorite animal? Do you a least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
11- What's your favorite restaurant? What’s your least favorite?
What have you learned about me that was new and/or surprising?
That one or two things that made you go hmmmm, OMG or wow!
17- Have you ever done drugs? Which ones? How often?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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)
36~ What is your favorite time of day to have sex/make love?
51~ Are you willing to play adult games with your partner?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
21~ What was the best date you ever went on? What has been the worst?
*** What’s Your Favorite…? ***
What is your favorite position? Why?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
How well do you know me? And some of your thoughts about me
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…
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
What do you dislike about me? I asked you to be 100% honest.
Family Relation Age Play
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What is your favorite toy? Ever wanted to try a specific toy?
21- What's your favorite way to spend a weekend or time off?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
How many times do you think you have “made love”?
Would you ever want to be woken up with oral and/or intercourse?
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?
Does the thought excite you? Care to share?
10- What is your favorite family tradition? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
29- How superstitious are you?
18- How often do you drink alcohol? What is your favorite drink?
1~ How old were you when you had your first kiss? Who? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
If YES, was it with 2 men or 2 women? Did you enjoy it?
8- What are your thoughts on politics?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Nothing too Serious
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
15- What's your favorite saying? What word or phrase is your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
42~ What’s your biggest regret in life?
9- Is there something you’ve always wanted to ask me but you’re afraid?
27- What was/ is nickname? Does it have a meaning behind it?
Do you like it when they show and tell you what they want?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Can you Deep Throat? Do you like the taste of yourself?
6- Do you have dreams? Can you remember them? What do you usually dream about?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
32- What's your greatest talent? Can I see it right now?
22- What is your favorite childhood memory? What is your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
1- What was your first impression of me? Has it changed?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
5~ When you first started having sex, was it what you thought it would be?
Repairman/Lonely Wife Virgin/Experienced
What have you learned about yourself that you did not before this?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
37- Do you like your name? If you could change it, what would you change it too?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
*** Random Questions ***
70~ Would/do you have/like anal sex?
*** Questions About Me ***
52~ What are your hobbies?
Get this wrong and this could mean the end… :-) some funny, some not…
89~ Do you like taking showers together?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
49~ How many times have you been married? Why did they end?
Nurse/Patient Celebrity/Fan
60~ How important is oral sex? Do you like receiving? Do you like giving?
39~ What are your love languages?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
Would you read them together?
3- Should Pluto still be considered a planet? 4- How about smoking?
Prisoner/Prison Guard Landlord/Tenant
If you say it, I will stop, and we can talk about it when you are ready.
12- What’s your favorite food? What’s your least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
33- If you could visit any time period, when would you pick? Please explain why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
28~ What are some things that turn on? What is your biggest turn on?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
2- What’s your favorite color? Do you a least favorite?
12- What is the weirdest thing you've ever eaten?
20- What’s your favorite candy? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
81~ Do you have any kinks and/or fetishes?
Do you like the “69” position? Do you prefer to be on top or bottom?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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…)
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)
51~ What tends to bring a smile to your face?