What is the most interesting question you can ask to get to know someone?
Last Updated: 24.06.2025 14:40
What do you dislike about me? I asked you to be 100% honest.
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
48~ Have you ever paid or been paid for sex?
Michaels buys Joann brand, plans to expand crafting supply to meet demand - ABC News
How about if they talk dirty and/or call you names?
80~ Share your top three fantasies/desires. (Be detailed) đ
33- If you could visit any time period, when would you pick? Please explain why?
11- List at least 5 things on your bucket list. Have you done any of them already?
I would allow you to do it⌠What would you do to me?
50~ How many children do you have? What are their ages?
Photos: Why it took courage for these women to pose for the camera - NPR
12- Whatâs your favorite food? Whatâs your least favorite?
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)
8- What are your thoughts on politics?
The Ozempic era is forcing wellness retreats for the elite to change - The Washington Post
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Is Russiaâs evacuation of navy ships from Syria a sign of declining influence in the Middle East?
What is your favorite toy? Ever wanted to try a specific toy?
Would you ever want to be woken up with oral and/or intercourse?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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If YES, was it with 2 men or 2 women? Did you enjoy it?
83~ How do you feel about Porn?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Whoâs the smartest Hollywood celebrity?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Can you Deep Throat? Do you like the taste of yourself?
How can I easily get rid of my writers block?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
The Ice Breaker Questions
42~ Whatâs your biggest regret in life?
Why are people saying that Taylor Swift is the smartest person on Earth?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
3- What was the most surprising thing youâve learned about me throughout our relationship?
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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52~ What are your hobbies?
Have you ever? Care to Share?
70~ Would/do you have/like anal sex?
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66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
65~ Describe the best orgasm youâve ever had? Care to share?
Prisoner/Prison Guard Landlord/Tenant
13- Whatâs your favorite drink? Whatâs your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
Any that are a turn off?
21~ What was the best date you ever went on? What has been the worst?
19- Do/have you smoked? What do you prefer? How often?
34~ Do you like the lights on or off during sex?
62~ Have you used adult toys?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
38~ Share your most embarrassing sexual memory?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
11~ Have you ever been caught by your parents or children or others while having sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
61~ How willing would you be to try new sexual positions?
Escort/Client Job Applicant/Hiring Manager
18~ Who/when was your first âcrushâ?
Any that are a turn off?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Do you think this brought you closer together?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
19~ Who/when was your first âheartbreakâ?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
40~ Whatâs the weirdest place youâve ever had sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
28~ What are some things that turn on? What is your biggest turn on?
Would you do it again, and would you rather 2 females or 2 males?
92~ Have you ever had or have an STD? How many? What was it?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Model/Photographer Police/Criminal
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?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Does the thought excite you? Care to share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
9- Whatâs your favorite season and why? Whatâs your least favorite?
13- How about having a certain hair cut/style?
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?
28- What are some things that people do that irritate you?
2- Whatâs your favorite color? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
14 â Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
5~ When you first started having sex, was it what you thought it would be?
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 togetherâŚ
How well do you know me? And some of your thoughts about me
10- List 5 of your top pet peeves.
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
89~ Do you like taking showers together?
Would you read them together?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
51~ Are you willing to play adult games with your partner?
9- Is there something youâve always wanted to ask me but youâre afraid?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Will you cheat again? How can, you be sure? Define what cheating is to you.
That one or two things that made you go hmmmm, OMG or wow!
17- Whatâs your favorite holiday? Whatâs your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
51~ What tends to bring a smile to your face?
32- What's your greatest talent? Can I see it right now?
81~ Do you have any kinks and/or fetishes?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
What have you learned about yourself that you did not before this?
How many partners have you had oral sex with? Who? Care to Share?
Nothing too Serious
If you say it, I will stop, and we can talk about it when you are ready.
23- What is your dream job? What was it as a child?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
20- Whatâs your favorite candy? Whatâs your least favorite?
37- Do you like your name? If you could change it, what would you change it too?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
26~ What side of the bed do you sleep on?
39~ What are your love languages?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
* Give a rating for each one (0-100)
Nurse/Patient Celebrity/Fan
11- What's your favorite restaurant? Whatâs your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
18- How often do you drink alcohol? What is your favorite drink?
49~ How many times have you been married? Why did they end?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
31- If given a chance to be immortal, would you take it? Why?
3- What Superhero or Superpower would you want to be/have?
13~ Is there a difference between, making love, having sex, and fucking?
Do you like the â69â position? Do you prefer to be on top or bottom?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
48~ Do you have any siblings? Are you close to your family?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Please share Did you stop?
If yes, what?
How old are you? Male or Female?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
36~ What is your favorite time of day to have sex/make love?
4- For a pet, Cat, dog or other?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Family Relation Age Play
9- If you could have three wishes, what would they be? Why?
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?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
84~ How do you feel about reading/listening to adult stories?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
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)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** Deal Breaker Questions ***
What would you say to prove to yourself that it was really you?
25~ How do you feel about PDA? (Public Display of Affection)
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
*** Questions About Me ***
21- What's your favorite way to spend a weekend or time off?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
44~ Care to share something about yourself that no one else knows about you?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
76~ Have you had a threesome? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
1- What was your first impression of me? Has it changed?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Doctor/Nurse Stripper/Client
92~ Everyone needs a âsafeâ word. What is yours?
Over time has your thoughts on sex changed?
5- Have you ever been hypnotized? Would you allow yourself to be?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
12- What is the weirdest thing you've ever eaten?
85~ If you gave me a âfree Passâ to have me do anything for one hour, what would you want me to do to you?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
3- Should Pluto still be considered a planet? 4- How about smoking?
3- Whatâs your favorite smell? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
15- What's your favorite saying? What word or phrase is your least favorite?
15~ Have you ever been âin loveâ? Who? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
29- How superstitious are you?
52~ Are you willing to make âthose typesâ of bets with your partner?
Would /have you ever given your partner a lap dance and Striptease?
Teacher/Student Stranger/One Night Stand
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
(Dildo, vibrator, nipple clamp, cock ring, butt plug and tail, couplesâ toys, pocket pussy/sleeves, Ben-wa balls, pumps, gags, strap-on, remote controlled, vibrating panties, ETCâŚ)
Would you mind if your partner watched it? How about together vs alone?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What have you learned about me that was new and/or surprising?
60~ How important is oral sex? Do you like receiving? Do you like giving?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
You know that I will be 100% truthful, so ask.
22- What is your favorite childhood memory? What is your least favorite?
What was the longest? What was the shortest?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
34- Ever been to a concert? What was your favorite? Who would you like to see?
33- Beach or Mountains? Or is there another place to like better?
22- Do you have any birth marks? How about scars? Care to share how you got them?
What is your favorite position? Why?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
53~ How much can you tell me about the one thing you are most passionate about?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What is your view on sex? Meaning, When/Where/ How often/
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
47~ What would be your dream job and why?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
Master/Slave Boss/Maid
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
36- Do you play video games? What is your favorite? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
9~ How many times over your lifetime do you think you have had sex so far?
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 âPASSâ 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 yourselfâŚ
10- What is your favorite family tradition? Whatâs your least favorite?
Do you have a favorite? Is it ok if your partner does?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If you win, what will you make them do?
17- Have you ever done drugs? Which ones? How often?
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?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
6- Do you have dreams? Can you remember them? What do you usually dream about?
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
*** Random Questions ***
11- How about if they like a certain sports team? 12-How about drinking too much?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
27- What was/ is nickname? Does it have a meaning behind it?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Do you like it when they show and tell you what they want?
7- What are your thoughts on religion? Is there an afterlife?
85~ If I gave you a âFree Passâ for you to do anything to me for one hour, knowing that no matter what you did,
1- Whatâs your favorite animal? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
*** Questions about Relationships/Past ***
14- What's your favorite dessert? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
13- What is the craziest/scariest thing you've ever done?
How many times do you think you have âmade loveâ?
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?
10~ How many dates are necessary before you to have sex with someone?
14- Do you have a âDeal Breakerâ, anything that your partner has done or will do, a boundary that once crossed you are done with the relationships?
30~ What's something unexpected that turns you on?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you watch it? What is your favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Repairman/Lonely Wife Virgin/Experienced
*** Whatâs Your FavoriteâŚ? ***
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
1~ How old were you when you had your first kiss? Who? Care to Share?