What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 12:17
If you win, what will you make them do?
80~ Share your top three fantasies/desires. (Be detailed) đ
* Give a rating for each one (0-100)
What does pompano fish taste like?
9- Is there something youâve always wanted to ask me but youâre afraid?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Which company offers affordable HVAC services in NY?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
76~ Have you had a threesome? Care to Share?
What is your favorite position? Why?
What are the ethical implications of using AI in recruitment and hiring processes?
If you say it, I will stop, and we can talk about it when you are ready.
What would you say to prove to yourself that it was really you?
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
34~ Do you like the lights on or off during sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
âThe Bearâ Season 4 Finale Leaves Us With Plenty to Chew On - Rolling Stone
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you have a favorite? Is it ok if your partner does?
Would you mind if your partner watched it? How about together vs alone?
Will you cheat again? How can, you be sure? Define what cheating is to you.
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŚ
9- If you could have three wishes, what would they be? Why?
2- Whatâs your favorite color? Do you a least favorite?
If you were to write a book about being a K-pop fan, what would the last sentence be?
Do you think this brought you closer together?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Show 1433: What Are the Hidden Dangers in the Air We Breathe? - The People's Pharmacy
Do you like it when they show and tell you what they want?
Do you like the â69â position? Do you prefer to be on top or bottom?
5~ When you first started having sex, was it what you thought it would be?
Have you ever had a scary dream about a loved one or friend soon after their death?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
10- What is your favorite family tradition? Whatâs your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
What have you learned about yourself that you did not before this?
11- List at least 5 things on your bucket list. Have you done any of them already?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
5- Have you ever been hypnotized? Would you allow yourself to be?
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
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
23 Doctors Who Said Something Crass, Cruel, Or CRINGEY To Their Patients - BuzzFeed
32- What's your greatest talent? Can I see it right now?
(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)
How about if they talk dirty and/or call you names?
1- Whatâs your favorite animal? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Can you Deep Throat? Do you like the taste of yourself?
82~ Do you have any fantasies involving Role-Playing?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Would you ever want to be woken up with oral and/or intercourse?
*** Questions about Relationships/Past ***
13- How about having a certain hair cut/style?
42~ Whatâs your biggest regret in life?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
3- Should Pluto still be considered a planet? 4- How about smoking?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
How many partners have you had oral sex with? Who? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
26~ What side of the bed do you sleep on?
That one or two things that made you go hmmmm, OMG or wow!
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Over time has your thoughts on sex changed?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
3- What was the most surprising thing youâve learned about me throughout our relationship?
37- Do you like your name? If you could change it, what would you change it too?
Prisoner/Prison Guard Landlord/Tenant
92~ Everyone needs a âsafeâ word. What is yours?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
81~ Do you have any kinks and/or fetishes?
Would you do it again, and would you rather 2 females or 2 males?
Does the thought excite you? Care to share?
*** Whatâs Your FavoriteâŚ? ***
Piecing, tattoo, color hair, dress up a certain way, it could be anything⌠Shave meâŚ
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Get this wrong and this could mean the end⌠:-) some funny, some notâŚ
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Model/Photographer Police/Criminal
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
36- Do you play video games? What is your favorite? Do you a least favorite?
Any that are a turn off?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
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?
If yes, what?
39~ What are your love languages?
3- Whatâs your favorite smell? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
28~ What are some things that turn on? What is your biggest turn on?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
7- What if a person smells a certain way? 8- How about smoking?
18~ Who/when was your first âcrushâ?
Have you ever? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
36~ What is your favorite time of day to have sex/make love?
The Ice Breaker Questions
40~ Whatâs the weirdest place youâve ever had sex?
How many times do you think you have âmade loveâ?
52~ What are your hobbies?
29~ What are some things that turn you off? What is your biggest turn off?
70~ Would/do you have/like anal 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?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
11- How about if they like a certain sports team? 12-How about drinking too much?
48~ Do you have any siblings? Are you close to your family?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
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
65~ Describe the best orgasm youâve ever had? Care to share?
How old are you? Male or Female?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
11~ Have you ever been caught by your parents or children or others while having sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
47~ What would be your dream job and why?
Master/Slave Boss/Maid
19- Do/have you smoked? What do you prefer? How often?
48~ Have you ever paid or been paid for sex?
1- What was your first impression of me? Has it changed?
9~ How many times over your lifetime do you think you have had sex so far?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
53~ How much can you tell me about the one thing you are most passionate about?
Family Relation Age Play
12- What is the weirdest thing you've ever eaten?
19- Whatâs your favorite fairytale? Whatâs your least favorite?
*** Deal Breaker Questions ***
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
62~ Have you used adult toys?
17- Whatâs your favorite holiday? Whatâs your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
9- Whatâs your favorite season and why? Whatâs your least favorite?
What was the longest? What was the shortest?
22- Do you have any birth marks? How about scars? Care to share how you got them?
12- Whatâs your favorite food? Whatâs your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
51~ Are you willing to play adult games with your partner?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How well do you know me? And some of your thoughts about me
Teacher/Student Stranger/One Night Stand
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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,
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
Please share Did you stop?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
14- What's your favorite dessert? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you watch it? What is your favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŚ
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If YES, was it with 2 men or 2 women? Did you enjoy it?
52~ Are you willing to make âthose typesâ of bets with your partner?
21- What's your favorite way to spend a weekend or time off?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
4- For a pet, Cat, dog or other?
89~ Do you like taking showers together?
15~ Have you ever been âin loveâ? Who? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear 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?
Would /have you ever given your partner a lap dance and Striptease?
28- What are some things that people do that irritate you?
14- What is an embarrassing moment in your life? How about your most embarrassing?
13- What is the craziest/scariest thing you've ever done?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What have you learned about me that was new and/or surprising?
15- What bad habit do you wish you could quit? Do you have any addictions?
7- What are your thoughts on religion? Is there an afterlife?
18- How often do you drink alcohol? What is your favorite drink?
19~ Who/when was your first âheartbreakâ?
13- Whatâs your favorite drink? Whatâs your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
50~ How many children do you have? What are their ages?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
21~ What was the best date you ever went on? What has been the worst?
20- Whatâs your favorite candy? Whatâs your least favorite?
I would allow you to do it⌠What would you do to me?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
38~ Share your most embarrassing sexual memory?
Doctor/Nurse Stripper/Client
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
51~ What tends to bring a smile to your face?
Would you read them together?
61~ How willing would you be to try new sexual positions?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Random Questions ***
64~ When was your very first orgasm? When was your first from having sex? Care to share?
83~ How do you feel about Porn?
10- List 5 of your top pet peeves.
What do you dislike about me? I asked you to be 100% honest.
44~ Care to share something about yourself that no one else knows about you?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
34- Ever been to a concert? What was your favorite? Who would you like to see?
31- If given a chance to be immortal, would you take it? Why?
Whatâs the longest time you gone without having sex, after, having it? How much time between the others?
Nurse/Patient Celebrity/Fan
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
8- What are your thoughts on politics?
30~ What's something unexpected that turns you on?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Take the short quiz here @ Discover Your Love LanguageÂŽ - The 5 Love LanguagesÂŽ
84~ How do you feel about reading/listening to adult stories?
Any that are a turn off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What is your view on sex? Meaning, When/Where/ How often/
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?
29- How superstitious are you?
Nothing too Serious
49~ How many times have you been married? Why did they end?
You know that I will be 100% truthful, so ask.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
33- If you could visit any time period, when would you pick? Please explain why?
3- What Superhero or Superpower would you want to be/have?
33- Beach or Mountains? Or is there another place to like better?
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
*** Questions About Me ***
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
27- What was/ is nickname? Does it have a meaning behind it?
Escort/Client Job Applicant/Hiring Manager
17- Have you ever done drugs? Which ones? How often?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
11- What's your favorite restaurant? Whatâs your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
23- What is your dream job? What was it as a child?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
15- What's your favorite saying? What word or phrase is your least favorite?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?