What is the most interesting question you can ask to get to know someone?
Last Updated: 28.06.2025 01:16
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
What are the most shocking facts about the Bollywood industry?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
53~ How much can you tell me about the one thing you are most passionate about?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Lexi Wood Exits Bravo’s ‘Summer House’ After 1 Season - Deadline
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
65~ Describe the best orgasm you’ve ever had? Care to share?
12- What is the weirdest thing you've ever eaten?
US lawmakers fire back a response to Trump's NASA cuts - theregister.com
11- List at least 5 things on your bucket list. Have you done any of them already?
Would you ever want to be woken up with oral and/or intercourse?
If YES, was it with 2 men or 2 women? Did you enjoy it?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3- What Superhero or Superpower would you want to be/have?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Volcanic Eruptions Can Create Ice in The Sky, And We Finally Know How - ScienceAlert
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)
Repairman/Lonely Wife Virgin/Experienced
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
James Bond game 007 First Light gets first trailer - The Verge
51~ What tends to bring a smile to your face?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
10~ How many dates are necessary before you to have sex with someone?
How powerful is LinkedIn for job ads?
Would you read them together?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Mars isn’t Red? The Planet is Actually… - The Daily Galaxy
28- What are some things that people do that irritate you?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
Aphantasia: Why Some Minds Are Blind to Images - Neuroscience News
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Poll: Is Xbox heading in the right direction? Cast your vote here! - Windows Central
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
How well do you know me? And some of your thoughts about me
Do very hot men ever feel attracted to an ugly woman? Why?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
34~ Do you like the lights on or off during sex?
When gallery photos are deleted at the same time, why are Google photos also deleted?
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?
Doctor/Nurse Stripper/Client
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
7- What are your thoughts on religion? Is there an afterlife?
38~ Share your most embarrassing sexual memory?
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?
What have you learned about me that was new and/or surprising?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
29~ What are some things that turn you off? What is your biggest turn off?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Have you ever? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
21~ What was the best date you ever went on? What has been the worst?
*** Deal Breaker Questions ***
61~ How willing would you be to try new sexual positions?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
34- Ever been to a concert? What was your favorite? Who would you like to see?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
I would allow you to do it… What would you do to me?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Teacher/Student Stranger/One Night Stand
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
If yes, what?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
67~ Do you like it when your partner moans and/or is vocal during sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Nurse/Patient Celebrity/Fan
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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~ Are you willing to play adult games with your partner?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
What would you say to prove to yourself that it was really you?
17- Have you ever done drugs? Which ones? How often?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Master/Slave Boss/Maid
*** Questions About Me ***
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
36~ What is your favorite time of day to have sex/make love?
5- Have you ever been hypnotized? Would you allow yourself to be?
11~ Have you ever been caught by your parents or children or others while having sex?
13- What’s your favorite drink? What’s your least favorite?
Do you like it when they show and tell you what they want?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What was the longest? What was the shortest?
32- What's your greatest talent? Can I see it right now?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
3- What’s your favorite smell? Do you a least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
42~ What’s your biggest regret in life?
10- List 5 of your top pet peeves.
4- For a pet, Cat, dog or other?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would /have you ever given your partner a lap dance and Striptease?
81~ Do you have any kinks and/or fetishes?
Do you like the “69” position? Do you prefer to be on top or bottom?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
7- What if a person smells a certain way? 8- How about smoking?
How many times do you think you have “made love”?
19- What’s your favorite fairytale? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
39~ What are your love languages?
13- What is the craziest/scariest thing you've ever done?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Escort/Client Job Applicant/Hiring Manager
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Will you cheat again? How can, you be sure? Define what cheating is to you.
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
19~ Who/when was your first “heartbreak”?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
29- How superstitious are you?
Do you think this brought you closer together?
If you win, what will you make them do?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
47~ What would be your dream job and why?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
13- How about having a certain hair cut/style?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
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…
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
25~ How do you feel about PDA? (Public Display of Affection)
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?
15- What's your favorite saying? What word or phrase is your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Do you watch it? What is your favorite?
How old are you? Male or Female?
1~ How old were you when you had your first kiss? Who? Care to Share?
Model/Photographer Police/Criminal
What have you learned about yourself that you did not before this?
18~ Who/when was your first “crush”?
92~ Have you ever had or have an STD? How many? What was it?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
21- What's your favorite way to spend a weekend or time off?
89~ Do you like taking showers together?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
9- If you could have three wishes, what would they be? Why?
92~ Everyone needs a “safe” word. What is yours?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Family Relation Age Play
* Give a rating for each one (0-100)
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
27- What was/ is nickname? Does it have a meaning behind it?
37- Do you like your name? If you could change it, what would you change it too?
If NO, would you ever have one? Would it be with 2 men or 2 women?
10- What is your favorite family tradition? What’s your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Over time has your thoughts on sex changed?
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 is your favorite toy? Ever wanted to try a specific toy?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
What do you dislike about me? I asked you to be 100% honest.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
62~ Have you used adult toys?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
52~ Are you willing to make “those types” of bets with your partner?
*** Random Questions ***
14- What's your favorite dessert? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
19- Do/have you smoked? What do you prefer? How often?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Does the thought excite you? Care to share?
2- What’s your favorite color? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
6- Do you have dreams? Can you remember them? What do you usually dream about?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Any that are a turn off?
Would you do it again, and would you rather 2 females or 2 males?
48~ Have you ever paid or been paid for sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
49~ How many times have you been married? Why did they end?
1- What was your first impression of me? Has it changed?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Nothing too Serious
83~ How do you feel about Porn?
Do you have a favorite? Is it ok if your partner does?
52~ What are your hobbies?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
84~ How do you feel about reading/listening to adult stories?
Prisoner/Prison Guard Landlord/Tenant
12- What’s your favorite food? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
50~ How many children do you have? What are their ages?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
30~ What's something unexpected that turns you on?
What is your favorite position? 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.
That one or two things that made you go hmmmm, OMG or wow!
Any that are a turn off?
70~ Would/do you have/like anal sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
33- Beach or Mountains? Or is there another place to like better?
*** Questions about Relationships/Past ***
3- Should Pluto still be considered a planet? 4- How about smoking?
76~ Have you had a threesome? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
1- What’s your favorite animal? Do you a least favorite?
The Ice Breaker Questions
28~ What are some things that turn on? What is your biggest turn on?
7-What do I do in bed that drives you wild? How about, what turns you off?
23- What is your dream job? What was it as a child?
9- What’s your favorite season and why? What’s your least favorite?
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?
40~ What’s the weirdest place you’ve ever had sex?
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,
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Get this wrong and this could mean the end… :-) some funny, some not…
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
48~ Do you have any siblings? Are you close to your family?
What is your view on sex? Meaning, When/Where/ How often/
44~ Care to share something about yourself that no one else knows about you?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How about if they talk dirty and/or call you names?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
26~ What side of the bed do you sleep on?
31- If given a chance to be immortal, would you take it? Why?
20- What’s your favorite candy? What’s your least favorite?
You know that I will be 100% truthful, so ask.
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you allow me to clean every part of your body with my soapy hands and fingers?
(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…)
Would you mind if your partner watched it? How about together vs alone?
22- What is your favorite childhood memory? What is your least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Can you Deep Throat? Do you like the taste of yourself?
8- What are your thoughts on politics?
Please share Did you stop?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
*** What’s Your Favorite…? ***
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…
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?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How many partners have you had oral sex with? Who? Care to Share?