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