What is the most interesting question you can ask to get to know someone?
Last Updated: 28.06.2025 06:32
46~ Have you ever used furniture, or other types of things to aid you while having sex?
89~ Do you like taking showers together?
48~ Do you have any siblings? Are you close to your family?
Why in my 60s do I have a strong desire to suck cock and swallow?
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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How many partners have you had oral sex with? Who? Care to Share?
Have you ever? Care to Share?
83~ How do you feel about Porn?
2- What’s your favorite color? Do you a least favorite?
Has anyone ever really waited that long and gotten a paper check mailed 20 days ago?
Can you Deep Throat? Do you like the taste of yourself?
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?
29- How superstitious are you?
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3- What was the most surprising thing you’ve learned about me throughout our relationship?
5~ When you first started having sex, was it what you thought it would be?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Can we buy cheap whey protein from an Amazon brand like Nakpro Power US? Is it safe to eat?
What have you learned about me that was new and/or surprising?
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?
*** What’s Your Favorite…? ***
Astronomers see the 1st stars dispel darkness 13 billion years ago at 'Cosmic Dawn' - Space
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…
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
How many downloads does an iOS app need to get into the top charts in education?
11- How about if they like a certain sports team? 12-How about drinking too much?
What have you learned about yourself that you did not before this?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Why is there no great temptress figure in any of Tolkien’s major works?
11~ Have you ever been caught by your parents or children or others while having sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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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?
61~ How willing would you be to try new sexual positions?
How well do you know me? And some of your thoughts about me
Is India currently capable of implementing a multimodal artificial intelligence system?
21- What's your favorite way to spend a weekend or time off?
Any that are a turn off?
36- Do you play video games? What is your favorite? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
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,
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)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
80~ Share your top three fantasies/desires. (Be detailed) 😊
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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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?
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?
Nurse/Patient Celebrity/Fan
21~ What was the best date you ever went on? What has been the worst?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
62~ Have you used adult toys?
60~ How important is oral sex? Do you like receiving? Do you like giving?
51~ What tends to bring a smile to your face?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
13~ Is there a difference between, making love, having sex, and fucking?
14- What's your favorite dessert? Do you a least favorite?
*** Deal Breaker Questions ***
6- Do you have dreams? Can you remember them? What do you usually dream about?
7- What are your thoughts on religion? Is there an afterlife?
22- Do you have any birth marks? How about scars? Care to share how you got them?
82~ Do you have any fantasies involving Role-Playing?
37- Do you like your name? If you could change it, what would you change it too?
25~ How do you feel about PDA? (Public Display of Affection)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
1- What was your first impression of me? Has it changed?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
13- How about having a certain hair cut/style?
20- What’s your favorite candy? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Would you ever want to be woken up with oral and/or intercourse?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
18- How often do you drink alcohol? What is your favorite drink?
What is your favorite position? Why?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
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?
36~ What is your favorite time of day to have sex/make love?
If yes, what?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Model/Photographer Police/Criminal
18~ Who/when was your first “crush”?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
33- If you could visit any time period, when would you pick? Please explain why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
15- What's your favorite saying? What word or phrase is your least favorite?
What was the longest? What was the shortest?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Doctor/Nurse Stripper/Client
Do you think this brought you closer together?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Please share Did you stop?
7-What do I do in bed that drives you wild? How about, what turns you off?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
13- What is the craziest/scariest thing you've ever done?
15~ Have you ever been “in love”? Who? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
23- What is your dream job? What was it as a child?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
12- What is the weirdest thing you've ever eaten?
Nothing too Serious
What do you dislike about me? I asked you to be 100% honest.
28~ What are some things that turn on? What is your biggest turn on?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
5- Have you ever been hypnotized? Would you allow yourself to be?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
Over time has your thoughts on sex changed?
(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- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
*** Random Questions ***
14- What is an embarrassing moment in your life? How about your most embarrassing?
9~ How many times over your lifetime do you think you have had sex so far?
81~ Do you have any kinks and/or fetishes?
49~ How many times have you been married? Why did they end?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Will you cheat again? How can, you be sure? Define what cheating is to you.
19- Do/have you smoked? What do you prefer? How often?
If YES, was it with 2 men or 2 women? Did you enjoy it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
13- What’s your favorite drink? What’s your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
4- For a pet, Cat, dog or other?
Prisoner/Prison Guard Landlord/Tenant
1- What’s your favorite animal? Do you a least favorite?
12- What’s your favorite food? What’s your least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Get this wrong and this could mean the end… :-) some funny, some not…
92~ Have you ever had or have an STD? How many? What was it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
92~ Everyone needs a “safe” word. What is yours?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Do you watch it? What is your favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
10- List 5 of your top pet peeves.
* Give a rating for each one (0-100)
What is your favorite toy? Ever wanted to try a specific toy?
3- Should Pluto still be considered a planet? 4- How about smoking?
27- What was/ is nickname? Does it have a meaning behind it?
10~ How many dates are necessary before you to have sex with someone?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
17- Have you ever done drugs? Which ones? How often?
8- What are your thoughts on politics?
Would you allow me to clean every part of your body with my soapy hands and fingers?
How about if they talk dirty and/or call you names?
39~ What are your love languages?
Do you like it when they show and tell you what they want?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you mind if your partner watched it? How about together vs alone?
If you win, what will you make them do?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
31- If given a chance to be immortal, would you take it? Why?
3- What Superhero or Superpower would you want to be/have?
Any that are a turn off?
51~ Are you willing to play adult games with your partner?
50~ How many children do you have? What are their ages?
Would /have you ever given your partner a lap dance and Striptease?
28- What are some things that people do that irritate you?
Family Relation Age Play
You know that I will be 100% truthful, so ask.
40~ What’s the weirdest place you’ve ever had sex?
65~ Describe the best orgasm you’ve ever had? Care to share?
11- List at least 5 things on your bucket list. Have you done any of them already?
What is your view on sex? Meaning, When/Where/ How often/
*** Questions About Me ***
15- What bad habit do you wish you could quit? Do you have any addictions?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
9- What’s your favorite season and why? What’s your least favorite?
Do you have a favorite? Is it ok if your partner does?
34- Ever been to a concert? What was your favorite? Who would you like to see?
11- What's your favorite restaurant? What’s your least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
19- What’s your favorite fairytale? What’s your least favorite?
30~ What's something unexpected that turns you on?
*** Questions about Relationships/Past ***
9- If you could have three wishes, what would they be? Why?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Escort/Client Job Applicant/Hiring Manager
10- What is your favorite family tradition? What’s your least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
52~ What are your hobbies?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
22- What is your favorite childhood memory? What is your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
47~ What would be your dream job and why?
Would you do it again, and would you rather 2 females or 2 males?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
44~ Care to share something about yourself that no one else knows about you?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Repairman/Lonely Wife Virgin/Experienced
What would you say to prove to yourself that it was really you?
52~ Are you willing to make “those types” of bets with your partner?
Would you read them together?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
19~ Who/when was your first “heartbreak”?
9- Is there something you’ve always wanted to ask me but you’re afraid?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
The Ice Breaker Questions
Do you like the “69” position? Do you prefer to be on top or bottom?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
3- What’s your favorite smell? Do you a least favorite?
76~ Have you had a threesome? Care to Share?
I would allow you to do it… What would you do to me?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
67~ Do you like it when your partner moans and/or is vocal during sex?
70~ Would/do you have/like anal sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
1~ How old were you when you had your first kiss? Who? Care to Share?
34~ Do you like the lights on or off during sex?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
48~ Have you ever paid or been paid for sex?
32- What's your greatest talent? Can I see it right now?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Master/Slave Boss/Maid
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
How old are you? Male or Female?
33- Beach or Mountains? Or is there another place to like better?
Teacher/Student Stranger/One Night Stand
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
26~ What side of the bed do you sleep on?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
42~ What’s your biggest regret in life?
How many times do you think you have “made love”?
7- What if a person smells a certain way? 8- How about smoking?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
29~ What are some things that turn you off? What is your biggest turn off?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
84~ How do you feel about reading/listening to adult stories?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Does the thought excite you? Care to share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?