What is the most interesting question you can ask to get to know someone?
10.06.2025 05:31
18~ Who/when was your first “crush”?
Nothing too Serious
Model/Photographer Police/Criminal
Why is the government destroying the homeless instead of helping them?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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48~ Have you ever paid or been paid for sex?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
What do you dislike about me? I asked you to be 100% honest.
Can you Deep Throat? Do you like the taste of yourself?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Is it ethical for same-sex couples to raise children?
5- Have you ever been hypnotized? Would you allow yourself to be?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
* Give a rating for each one (0-100)
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32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Have you ever? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
1- What was your first impression of me? Has it changed?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
What caused the Democratic Party's 2024 presidential campaign to implode so horrifically?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
48~ Do you have any siblings? Are you close to your family?
33- If you could visit any time period, when would you pick? Please explain why?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
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7-What do I do in bed that drives you wild? How about, what turns you off?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Do you think the number of sissies is on the rise?
Please share Did you stop?
13~ Is there a difference between, making love, having sex, and fucking?
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)
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30~ What's something unexpected that turns you on?
29- How superstitious are you?
What is your favorite position? Why?
What does it mean when you dream that your mother died?
You know that I will be 100% truthful, so ask.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
15- What's your favorite saying? What word or phrase is your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Family Relation Age Play
If you say it, I will stop, and we can talk about it when you are ready.
13- How about having a certain hair cut/style?
7- What if a person smells a certain way? 8- How about smoking?
31- If given a chance to be immortal, would you take it? Why?
19- Do/have you smoked? What do you prefer? How often?
65~ Describe the best orgasm you’ve ever had? Care to share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Would you read them together?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
9- If you could have three wishes, what would they be? Why?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
83~ How do you feel about Porn?
Would /have you ever given your partner a lap dance and Striptease?
21~ What was the best date you ever went on? What has been the worst?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Any that are a turn off?
34~ Do you like the lights on or off during sex?
Prisoner/Prison Guard Landlord/Tenant
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,
67~ Do you like it when your partner moans and/or is vocal during sex?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
50~ How many children do you have? What are their ages?
How about if they talk dirty and/or call you names?
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?
21- What's your favorite way to spend a weekend or time off?
61~ How willing would you be to try new sexual positions?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
9- What’s your favorite season and why? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
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?
Over time has your thoughts on sex changed?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What would you say to prove to yourself that it was really you?
Escort/Client Job Applicant/Hiring Manager
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
80~ Share your top three fantasies/desires. (Be detailed) 😊
53~ How much can you tell me about the one thing you are most passionate about?
45~ How do you feel about me blindfolding you? How about blindfolding me?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you think this brought you closer together?
23- What is your dream job? What was it as a child?
17- Have you ever done drugs? Which ones? How often?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
4- For a pet, Cat, dog or other?
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?
*** What’s Your Favorite…? ***
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
*** Questions About Me ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What is your favorite toy? Ever wanted to try a specific toy?
17- What’s your favorite holiday? What’s your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
39~ What are your love languages?
3- What’s your favorite smell? Do you a least favorite?
Do you watch it? What is your favorite?
51~ Are you willing to play adult games with your partner?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
26~ What side of the bed do you sleep on?
If NO, would you ever have one? Would it be with 2 men or 2 women?
How old are you? Male or Female?
20- What’s your favorite candy? What’s your least favorite?
How well do you know me? And some of your thoughts about me
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
27- What was/ is nickname? Does it have a meaning behind it?
Do you like it when they show and tell you what they want?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
7- What are your thoughts on religion? Is there an afterlife?
Any that are a turn off?
89~ Do you like taking showers together?
47~ What would be your dream job and why?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
52~ What are your hobbies?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Teacher/Student Stranger/One Night Stand
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
25~ How do you feel about PDA? (Public Display of Affection)
15~ Have you ever been “in love”? Who? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
22- What is your favorite childhood memory? What is your least favorite?
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?
Repairman/Lonely Wife Virgin/Experienced
38~ Share your most embarrassing sexual memory?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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…
Master/Slave Boss/Maid
70~ Would/do you have/like anal sex?
40~ What’s the weirdest place you’ve ever had sex?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
13- What’s your favorite drink? What’s your least favorite?
*** Questions about Relationships/Past ***
51~ What tends to bring a smile to your face?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
The Ice Breaker Questions
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What have you learned about me that was new and/or surprising?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
If you win, what will you make them do?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
9- Is there something you’ve always wanted to ask me but you’re afraid?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Do you like the “69” position? Do you prefer to be on top or bottom?
84~ How do you feel about reading/listening to adult stories?
92~ Have you ever had or have an STD? How many? What was it?
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?
82~ Do you have any fantasies involving Role-Playing?
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- 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?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
62~ Have you used adult toys?
13- What is the craziest/scariest thing you've ever done?
52~ Are you willing to make “those types” of bets with your partner?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How many partners have you had oral sex with? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Get this wrong and this could mean the end… :-) some funny, some not…
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Would you do it again, and would you rather 2 females or 2 males?
What was the longest? What was the shortest?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
92~ Everyone needs a “safe” word. What is yours?
Would you ever want to be woken up with oral and/or intercourse?
71~ Would you give your partner a hand or foot job? Would you receive one?
*** Random Questions ***
10- What is your favorite family tradition? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
28- What are some things that people do that irritate you?
1- What’s your favorite animal? Do you a least favorite?
19~ Who/when was your first “heartbreak”?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
10- List 5 of your top pet peeves.
How many times do you think you have “made love”?
What is your view on sex? Meaning, When/Where/ How often/
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
2- What’s your favorite color? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
18- How often do you drink alcohol? What is your favorite drink?
*** Deal Breaker Questions ***
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
10~ How many dates are necessary before you to have sex with someone?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
36~ What is your favorite time of day to have sex/make love?
32- What's your greatest talent? Can I see it right now?
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.
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
12- What is the weirdest thing you've ever eaten?
11- List at least 5 things on your bucket list. Have you done any of them already?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
42~ What’s your biggest regret in life?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
29~ What are some things that turn you off? What is your biggest turn off?
What have you learned about yourself that you did not before this?
81~ Do you have any kinks and/or fetishes?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Nurse/Patient Celebrity/Fan
6- Do you have dreams? Can you remember them? What do you usually dream about?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
11- How about if they like a certain sports team? 12-How about drinking too much?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
I would allow you to do it… What would you do to me?
That one or two things that made you go hmmmm, OMG or wow!
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…
19- What’s your favorite fairytale? What’s your least favorite?
8- What are your thoughts on politics?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
3- Should Pluto still be considered a planet? 4- How about smoking?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
76~ Have you had a threesome? Care to Share?
Does the thought excite you? Care to share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
28~ What are some things that turn on? What is your biggest turn on?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you have a favorite? Is it ok if your partner does?
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?
11- What's your favorite restaurant? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
3- What Superhero or Superpower would you want to be/have?
33- Beach or Mountains? Or is there another place to like better?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
If yes, what?
12- What’s your favorite food? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
Doctor/Nurse Stripper/Client
34- Ever been to a concert? What was your favorite? Who would you like to see?
(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…)
14- What is an embarrassing moment in your life? How about your most embarrassing?