What is the most interesting question you can ask to get to know someone?
Last Updated: 27.06.2025 02:02
81~ Do you have any kinks and/or fetishes?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) đ
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50~ How many children do you have? What are their ages?
47~ What would be your dream job and why?
4- For a pet, Cat, dog or other?
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25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
38~ Share your most embarrassing sexual memory?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
How does someone start doing urban exploration?
Do you watch it? What is your favorite?
48~ Have you ever paid or been paid for sex?
I would allow you to do it⊠What would you do to me?
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21- What's your favorite way to spend a weekend or time off?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Would /have you ever given your partner a lap dance and Striptease?
Do you consider masturbating to porn cheating if you are married?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
76~ Have you had a threesome? Care to Share?
(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, ETCâŠ)
66~ Whatâs the shortest time itâs ever taken for you to have an orgasm? And the longest?
Escort/Client Job Applicant/Hiring Manager
What ended your relationship with your best friend?
67~ Do you like it when your partner moans and/or is vocal during sex?
92~ Everyone needs a âsafeâ word. What is yours?
42~ Whatâs your biggest regret in life?
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?
15- What bad habit do you wish you could quit? Do you have any addictions?
Can you Deep Throat? Do you like the taste of yourself?
What does the Turkish word çıplak mean?
33- Beach or Mountains? Or is there another place to like better?
61~ How willing would you be to try new sexual positions?
*** Deal Breaker Questions ***
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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3- What Superhero or Superpower would you want to be/have?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
40~ Whatâs the weirdest place youâve ever had sex?
11- What's your favorite restaurant? Whatâs your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
37- Do you like your name? If you could change it, what would you change it too?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
28- What are some things that people do that irritate you?
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13- Whatâs your favorite drink? Whatâs your least favorite?
14~ When was the first time you said, âI Love Youâ? (romantically) Did you mean it? Who? Care to Share?
65~ Describe the best orgasm youâve ever had? Care to share?
How many partners have you had oral sex with? Who? Care to Share?
7- Whatâs your favorite book? Do you have a favorite genre? Do you a least favorite?
That one or two things that made you go hmmmm, OMG or wow!
9- Whatâs your favorite season and why? Whatâs your least favorite?
26~ What side of the bed do you sleep on?
12- What is the weirdest thing you've ever eaten?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
36~ What is your favorite time of day to have sex/make love?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
6- Whatâs your favorite TV series? Do you have a favorite genre? Do you a least favorite?
29- How superstitious are you?
Prisoner/Prison Guard Landlord/Tenant
1- What was your first impression of me? Has it changed?
10- List 5 of your top pet peeves.
Model/Photographer Police/Criminal
54~ Would you ever go skinny dipping 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?
11~ Have you ever been caught by your parents or children or others while having sex?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
21~ What was the best date you ever went on? What has been the worst?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
32- What's your greatest talent? Can I see it right now?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
17- Whatâs your favorite holiday? Whatâs your least favorite?
Do you prefer your partnerâs pubic hair trimmed, Landing Strip, full bush or completely bare?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
19~ Who/when was your first âheartbreakâ?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
9~ How many times over your lifetime do you think you have had sex so far?
49~ How many times have you been married? Why did they end?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
You know that I will be 100% truthful, so ask.
How old are you? Male or Female?
Do you like the â69â position? Do you prefer to be on top or bottom?
9- Is there something youâve always wanted to ask me but youâre afraid?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
9- If you could have three wishes, what would they be? Why?
7-What do I do in bed that drives you wild? How about, what turns you off?
*** Whatâs Your FavoriteâŠ? ***
16~ Do you believe in âsoulmatesâ? Have you found yours? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
5~ When you first started having sex, was it what you thought it would be?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
39~ What are your love languages?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Family Relation Age Play
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?
25~ How do you feel about PDA? (Public Display of Affection)
52~ What are your hobbies?
71~ Would you give your partner a hand or foot job? Would you receive one?
*** Questions About Me ***
22- What is your favorite childhood memory? What is your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
30~ What's something unexpected that turns you on?
3- Should Pluto still be considered a planet? 4- How about smoking?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
7- What are your thoughts on religion? Is there an afterlife?
52~ Are you willing to make âthose typesâ of bets with your partner?
Does the thought excite you? Care to share?
51~ Are you willing to play adult games with your partner?
4- Whatâs your favorite genre of music? Whatâs your least favorite? Is there a song that triggers a memory?
13- What is the craziest/scariest thing you've ever done?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Would you mind if your partner watched it? How about together vs alone?
15- What's your favorite saying? What word or phrase is your least 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 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 yourselfâŠ
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
13~ Is there a difference between, making love, having sex, and fucking?
8- What are your thoughts on politics?
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72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
1- Whatâs your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
How many times do you think you have âmade loveâ?
89~ Do you like taking showers together?
* Give a rating for each one (0-100)
45~ How do you feel about me blindfolding you? How about blindfolding me?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
70~ Would/do you have/like anal sex?
48~ Do you have any siblings? Are you close to your family?
23- What is your dream job? What was it as a child?
15~ Have you ever been âin loveâ? Who? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Please share Did you stop?
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
8- What's something unexpected that turns you on that I do to you? Donât be shy now, I really want to know.
16- Whatâs your favorite vacation you have been on? Whatâs your least favorite? Where would you like to go?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
28~ What are some things that turn on? What is your biggest turn on?
60~ How important is oral sex? Do you like receiving? Do you like giving?
What is your view on sex? Meaning, When/Where/ How often/
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
Over time has your thoughts on sex changed?
How about if they talk dirty and/or call you names?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What is your favorite position? Why?
Would you allow me to clean every part of your body with my soapy hands and fingers?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
19- Whatâs your favorite fairytale? Whatâs your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
44~ Care to share something about yourself that no one else knows about you?
What have you learned about yourself that you did not before this?
Would you read them together?
7- What if a person smells a certain way? 8- How about smoking?
51~ What tends to bring a smile to your face?
Would you do it again, and would you rather 2 females or 2 males?
29~ What are some things that turn you off? What is your biggest turn off?
If NO, would you ever have one? Would it be with 2 men or 2 women?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
20- Whatâs your favorite candy? Whatâs your least favorite?
Do you think this brought you closer together?
Master/Slave Boss/Maid
13- How about having a certain hair cut/style?
82~ Do you have any fantasies involving Role-Playing?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
18~ Who/when was your first âcrushâ?
2- Whatâs your favorite color? Do you a least favorite?
83~ How do you feel about Porn?
8- What's your favorite flavor of ice cream? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
*** Random Questions ***
What was the longest? What was the shortest?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
19- Do/have you smoked? What do you prefer? How often?
12- Whatâs your favorite food? Whatâs your least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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
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?
Any that are a turn off?
Any that are a turn off?
What have you learned about me that was new and/or surprising?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
53~ How much can you tell me about the one thing you are most passionate about?
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 togetherâŠ
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
3- What was the most surprising thing youâve learned about me throughout our relationship?
How well do you know me? And some of your thoughts about me
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
88~ Do you prefer me to be naked or in lingerie, PJâs when you are sleeping?
3- Whatâs your favorite smell? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
27- What was/ is nickname? Does it have a meaning behind it?
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?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
14- What's your favorite dessert? Do you a least favorite?
Have you ever? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
34~ Do you like the lights on or off during sex?
If yes, what?
84~ How do you feel about reading/listening to adult stories?
Get this wrong and this could mean the end⊠:-) some funny, some notâŠ
What do you dislike about me? I asked you to be 100% honest.
Teacher/Student Stranger/One Night Stand
6- Do you have dreams? Can you remember them? What do you usually dream about?
5- Whatâs your favorite movie genre? Whatâs your favorite movie of all time? How many times have you watched it?
Meaning if you ever say it no matter how long we have been together or where we are in the momentâŠ
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
*** Questions about Relationships/Past ***
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
92~ Have you ever had or have an STD? How many? What was it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Piecing, tattoo, color hair, dress up a certain way, it could be anything⊠Shave meâŠ
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
62~ Have you used adult toys?
17- Have you ever done drugs? Which ones? How often?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Doctor/Nurse Stripper/Client
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
36- Do you play video games? What is your favorite? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
33- If you could visit any time period, when would you pick? Please explain why?
What would you say to prove to yourself that it was really you?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you ever want to be woken up with oral and/or intercourse?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
1- Whatâs your favorite animal? Do you a least favorite?
The Ice Breaker Questions
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,
Do you like it when they show and tell you what they want?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3âŠ
18- Whatâs your favorite way to relax after a long day? Whatâs your least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Nothing too Serious
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Nurse/Patient Celebrity/Fan
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
10- What is your favorite family tradition? Whatâs your least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
If you win, what will you make them do?
11- How about if they like a certain sports team? 12-How about drinking too much?
What is your favorite toy? Ever wanted to try a specific toy?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
22~ What is the best pickup line anyone has ever used on you? What was the worst?