What is the most interesting question you can ask to get to know someone?
Last Updated: 23.06.2025 10:05
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
22- Do you have any birth marks? How about scars? Care to share how you got them?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
*** Questions about Relationships/Past ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
18~ Who/when was your first “crush”?
Dementia risk begins in childhood, not old age, scientists warn - PsyPost
12- What’s your favorite food? What’s your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
If You Fit Into One Of These 6 Categories, You Should Be Taking Creatine - MindBodyGreen
You know that I will be 100% truthful, so ask.
47~ What would be your dream job and why?
Prisoner/Prison Guard Landlord/Tenant
52~ What are your hobbies?
25~ How do you feel about PDA? (Public Display of Affection)
44~ Care to share something about yourself that no one else knows about you?
‘Elio’ Is A Box Office Disaster, Pixar’s Lowest Opening Of All Time - Cartoon Brew
26~ What side of the bed do you sleep on?
9~ How many times over your lifetime do you think you have had sex so far?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
36- Do you play video games? What is your favorite? Do you a least favorite?
Telescope Captures First-Ever Ultra-Fine Magnetic Stripes on the Sun’s Surface! - The Daily Galaxy
13- How about having a certain hair cut/style?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you read them together?
19~ Who/when was your first “heartbreak”?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
21- What's your favorite way to spend a weekend or time off?
Sam Darnold on final games in Minnesota: "We laid an egg on offense" - NBC Sports
Repairman/Lonely Wife Virgin/Experienced
What do you dislike about me? I asked you to be 100% honest.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Does Trump have the authority to order U.S. strikes on Iran? - PBS
What is your favorite position? Why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Master/Slave Boss/Maid
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
14- What's your favorite dessert? Do you a least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
13~ Is there a difference between, making love, having sex, and fucking?
Teacher/Student Stranger/One Night Stand
37- Do you like your name? If you could change it, what would you change it too?
Have you ever? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
48~ Do you have any siblings? Are you close to your family?
40~ What’s the weirdest place you’ve ever had sex?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
The Ice Breaker Questions
7- What are your thoughts on religion? Is there an afterlife?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
50~ How many children do you have? What are their ages?
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?
Nothing too Serious
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
19- What’s your favorite fairytale? What’s your least favorite?
How old are you? Male or Female?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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…
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What was the longest? What was the shortest?
Model/Photographer Police/Criminal
13- What is the craziest/scariest thing you've ever done?
Do you watch it? What is your favorite?
34~ Do you like the lights on or off during sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
19- Do/have you smoked? What do you prefer? How often?
5- Have you ever been hypnotized? Would you allow yourself to be?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
33- If you could visit any time period, when would you pick? Please explain why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
71~ Would you give your partner a hand or foot job? Would you receive one?
45~ How do you feel about me blindfolding you? How about blindfolding me?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Please share Did you stop?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
Escort/Client Job Applicant/Hiring Manager
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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?
9- If you could have three wishes, what would they be? Why?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9- What’s your favorite season and why? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
38~ Share your most embarrassing sexual memory?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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?
That one or two things that made you go hmmmm, OMG or wow!
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
92~ Everyone needs a “safe” word. What is yours?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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,
(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…)
51~ What tends to bring a smile to your face?
81~ Do you have any kinks and/or fetishes?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
I would allow you to do it… What would you do to me?
8- What's your favorite flavor of ice cream? Do you a least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
11- List at least 5 things on your bucket list. Have you done any of them already?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
3- What Superhero or Superpower would you want to be/have?
Doctor/Nurse Stripper/Client
29~ What are some things that turn you off? What is your biggest turn off?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
28~ What are some things that turn on? What is your biggest turn on?
Family Relation Age Play
What is your favorite toy? Ever wanted to try a specific toy?
What have you learned about yourself that you did not before this?
If you win, what will you make them do?
89~ Do you like taking showers together?
13- What’s your favorite drink? What’s your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
5~ When you first started having sex, was it what you thought it would be?
76~ Have you had a threesome? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
*** Questions About Me ***
31- If given a chance to be immortal, would you take it? Why?
33- Beach or Mountains? Or is there another place to like better?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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?
12- What is the weirdest thing you've ever eaten?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
If you lose, are you willing to be their sex slave for a day, (anything goes)?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
49~ How many times have you been married? Why did they end?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
20- What’s your favorite candy? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Nurse/Patient Celebrity/Fan
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
How about if they talk dirty and/or call you names?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
*** Random Questions ***
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
17- What’s your favorite holiday? What’s your least favorite?
How well do you know me? And some of your thoughts about me
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
28- What are some things that people do that irritate you?
Do you think this brought you closer together?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
53~ How much can you tell me about the one thing you are most passionate about?
8- What are your thoughts on politics?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Any that are a turn off?
Get this wrong and this could mean the end… :-) some funny, some not…
48~ Have you ever paid or been paid for sex?
10- List 5 of your top pet peeves.
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Do you like the “69” position? Do you prefer to be on top or bottom?
Do you like it when they show and tell you what they want?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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)
What would you say to prove to yourself that it was really you?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Over time has your thoughts on sex changed?
If NO, would you ever have one? Would it be with 2 men or 2 women?
*** What’s Your Favorite…? ***
3- Should Pluto still be considered a planet? 4- How about smoking?
32- What's your greatest talent? Can I see it right now?
30~ What's something unexpected that turns you on?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
36~ What is your favorite time of day to have sex/make love?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
*** Deal Breaker Questions ***
Can you Deep Throat? Do you like the taste of yourself?
10~ How many dates are necessary before you to have sex with someone?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
7- What if a person smells a certain way? 8- How about smoking?
What is your view on sex? Meaning, When/Where/ How often/
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
18- How often do you drink alcohol? What is your favorite drink?
Does the thought excite you? Care to share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Would you ever want to be woken up with oral and/or intercourse?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
How many partners have you had oral sex with? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Would you mind if your partner watched it? How about together vs alone?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Any that are a turn off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If you say it, I will stop, and we can talk about it when you are ready.
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
23- What is your dream job? What was it as a child?
1- What was your first impression of me? Has it changed?
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?
39~ What are your love languages?
92~ Have you ever had or have an STD? How many? What was it?
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?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Would /have you ever given your partner a lap dance and Striptease?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
4- For a pet, Cat, dog or other?
Will you cheat again? How can, you be sure? Define what cheating is to you.
70~ Would/do you have/like anal sex?
2- What’s your favorite color? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
27- What was/ is nickname? Does it have a meaning behind it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
21~ What was the best date you ever went on? What has been the worst?
If yes, what?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
67~ Do you like it when your partner moans and/or is vocal during sex?
1- What’s your favorite animal? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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…
Do you have a favorite? Is it ok if your partner does?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
42~ What’s your biggest regret in life?
11- How about if they like a certain sports team? 12-How about drinking too much?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
10- What is your favorite family tradition? What’s your least favorite?
What have you learned about me that was new and/or surprising?
How many times do you think you have “made love”?
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)
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
51~ Are you willing to play adult games with your partner?
52~ Are you willing to make “those types” of bets with your partner?
62~ Have you used adult toys?
61~ How willing would you be to try new sexual positions?
22- What is your favorite childhood memory? What is your least favorite?
29- How superstitious are you?
82~ Do you have any fantasies involving Role-Playing?
83~ How do you feel about Porn?
34- Ever been to a concert? What was your favorite? Who would you like to see?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?