What is the most interesting question you can ask to get to know someone?
12.06.2025 03:29
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?
13- What is the craziest/scariest thing you've ever done?
Would /have you ever given your partner a lap dance and Striptease?
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 clean every part of your body with my soapy hands and fingers?
'Mission: Impossible 8': Inside How They Shot Underwater Submarine - IndieWire
*** What’s Your Favorite…? ***
Do you like it when they show and tell you what they want?
36- Do you play video games? What is your favorite? Do you a least favorite?
What celebrity do you admire the most?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Trump Media Raises $2.32B—Bitcoin Treasury and Big Moves Ahead - Bitcoin.com News
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
28~ What are some things that turn on? What is your biggest turn on?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What is the worst thing your sibling has done?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
92~ Have you ever had or have an STD? How many? What was it?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
How conservative the Japanese people really is? And the government?
9- What’s your favorite season and why? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
Master/Slave Boss/Maid
We white women don't like white men. Do you have any issue with that?
80~ Share your top three fantasies/desires. (Be detailed) 😊
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What was the longest? What was the shortest?
11- List at least 5 things on your bucket list. Have you done any of them already?
If NO, would you ever have one? Would it be with 2 men or 2 women?
How many partners have you had oral sex with? Who? Care to Share?
Supreme Court lets DOGE access Social Security data of millions of Americans - The Washington Post
9~ How many times over your lifetime do you think you have had sex so far?
Escort/Client Job Applicant/Hiring Manager
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
37~ What is the biggest age gap between you and one of your sexual partners? 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?
Can you Deep Throat? Do you like the taste of yourself?
Doctor/Nurse Stripper/Client
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
(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…)
22- What is your favorite childhood memory? What is your least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Repairman/Lonely Wife Virgin/Experienced
10- List 5 of your top pet peeves.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
8- What are your thoughts on politics?
47~ What would be your dream job and why?
Model/Photographer Police/Criminal
Prisoner/Prison Guard Landlord/Tenant
3- What Superhero or Superpower would you want to be/have?
52~ What are your hobbies?
21~ What was the best date you ever went on? What has been the worst?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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 do you dislike about me? I asked you to be 100% honest.
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
18~ Who/when was your first “crush”?
9- Is there something you’ve always wanted to ask me but you’re afraid?
34- Ever been to a concert? What was your favorite? Who would you like to see?
13- How about having a certain hair cut/style?
21- What's your favorite way to spend a weekend or time off?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
45~ How do you feel about me blindfolding you? How about blindfolding me?
What is your view on sex? Meaning, When/Where/ How often/
82~ Do you have any fantasies involving Role-Playing?
3- What’s your favorite smell? Do you a least favorite?
1- What’s your favorite animal? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
*** Random Questions ***
15- What bad habit do you wish you could quit? Do you have any addictions?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Have you ever? Care to Share?
Family Relation Age Play
Would you do it again, and would you rather 2 females or 2 males?
5- Have you ever been hypnotized? Would you allow yourself to be?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7- What if a person smells a certain way? 8- How about smoking?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
34~ Do you like the lights on or off during sex?
How well do you know me? And some of your thoughts about me
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?
51~ What tends to bring a smile to your face?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
19- What’s your favorite fairytale? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
84~ How do you feel about reading/listening to adult stories?
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)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
22- Do you have any birth marks? How about scars? Care to share how you got them?
17- Have you ever done drugs? Which ones? How often?
I would allow you to do it… What would you do to me?
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?
70~ Would/do you have/like anal sex?
15~ Have you ever been “in love”? Who? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
1~ How old were you when you had your first kiss? 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?
14- What's your favorite dessert? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
1- What was your first impression of me? Has it changed?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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,
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
You know that I will be 100% truthful, so ask.
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?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
What have you learned about yourself that you did not before this?
6- Do you have dreams? Can you remember them? What do you usually dream about?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Do you watch it? What is your favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
If you say it, I will stop, and we can talk about it when you are ready.
What is your favorite toy? Ever wanted to try a specific toy?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Over time has your thoughts on sex changed?
18- How often do you drink alcohol? What is your favorite drink?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
19~ Who/when was your first “heartbreak”?
67~ Do you like it when your partner moans and/or is vocal during sex?
11~ Have you ever been caught by your parents or children or others while having sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
29- How superstitious are you?
25~ How do you feel about PDA? (Public Display of Affection)
Any that are a turn off?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
*** Questions about Relationships/Past ***
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
If you win, what will you make them do?
Does the thought excite you? Care to share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
71~ Would you give your partner a hand or foot job? Would you receive one?
13- What’s your favorite drink? 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?
* Give a rating for each one (0-100)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
92~ Everyone needs a “safe” word. What is yours?
28- What are some things that people do that irritate you?
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?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
12- What is the weirdest thing you've ever eaten?
How old are you? Male or Female?
2- What’s your favorite color? Do you a least favorite?
48~ Do you have any siblings? Are you close to your family?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
That one or two things that made you go hmmmm, OMG or wow!
83~ How do you feel about Porn?
60~ How important is oral sex? Do you like receiving? Do you like giving?
44~ Care to share something about yourself that no one else knows about you?
51~ Are you willing to play adult games with your partner?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
12- What’s your favorite food? What’s your least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Please share Did you stop?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
30~ What's something unexpected that turns you on?
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…
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
7-What do I do in bed that drives you wild? How about, what turns you off?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
36~ What is your favorite time of day to have sex/make love?
How about if they talk dirty and/or call you names?
7- What are your thoughts on religion? Is there an afterlife?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
20- What’s your favorite candy? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
81~ Do you have any kinks and/or fetishes?
38~ Share your most embarrassing sexual memory?
48~ Have you ever paid or been paid for sex?
15- What's your favorite saying? What word or phrase is your least favorite?
5~ When you first started having sex, was it what you thought it would be?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
10~ How many dates are necessary before you to have sex with someone?
Would you ever want to be woken up with oral and/or intercourse?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
4- For a pet, Cat, dog or other?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
23- What is your dream job? What was it as a child?
39~ What are your love languages?
32- What's your greatest talent? Can I see it right now?
65~ Describe the best orgasm you’ve ever had? Care to share?
Teacher/Student Stranger/One Night Stand
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
11- What's your favorite restaurant? What’s your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
17- What’s your favorite holiday? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
*** Questions About Me ***
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Nothing too Serious
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
27- What was/ is nickname? Does it have a meaning behind it?
What is your favorite position? Why?
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…
What would you say to prove to yourself that it was really you?
What have you learned about me that was new and/or surprising?
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?
If yes, what?
62~ Have you used adult toys?
Get this wrong and this could mean the end… :-) some funny, some not…
76~ Have you had a threesome? Care to Share?
9- If you could have three wishes, what would they be? Why?
Would you read them together?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
The Ice Breaker Questions
42~ What’s your biggest regret in life?
89~ Do you like taking showers together?
Nurse/Patient Celebrity/Fan
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
3- Should Pluto still be considered a planet? 4- How about smoking?
11- How about if they like a certain sports team? 12-How about drinking too much?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you think this brought you closer together?
*** Deal Breaker Questions ***
Would you mind if your partner watched it? How about together vs alone?
29~ What are some things that turn you off? What is your biggest turn off?
31- If given a chance to be immortal, would you take it? Why?
Any that are a turn off?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
Will you cheat again? How can, you be sure? Define what cheating is to you.
How many times do you think you have “made love”?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
26~ What side of the bed do you sleep on?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
37- Do you like your name? If you could change it, what would you change it too?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…