What is the most interesting question you can ask to get to know someone?
14.06.2025 19:08
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,
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
8- What are your thoughts on politics?
Why has Biden pulled ahead in battleground states and is now projected to win the 2024 presidency?
*** Questions 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?
21~ What was the best date you ever went on? What has been the worst?
Teens like me, what are your expectations when entering adulthood?
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
What would be the lowest score with 9 strikes and no gutter balls?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Do you like it when they show and tell you what they want?
83~ How do you feel about Porn?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Teacher/Student Stranger/One Night Stand
Do flat Earthers really exist? Why do they believe the Earth is flat?
61~ How willing would you be to try new sexual positions?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Please share Did you stop?
What makes someone feel "rich enough" in different societies?
Can you Deep Throat? Do you like the taste of yourself?
22- Do you have any birth marks? How about scars? Care to share how you got them?
36- Do you play video games? What is your favorite? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
Will you cheat again? How can, you be sure? Define what cheating is to you.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
What is one fantasy you have never told anyone about but really want to do?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
6- Do you have dreams? Can you remember them? What do you usually dream about?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Why am I not getting any atheists to debate with? Are they scared?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
(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…)
Repairman/Lonely Wife Virgin/Experienced
How often do you watch the news on TV?
15~ Have you ever been “in love”? Who? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Measles strikes at birth: Six Canadian newborns infected from unvaccinated mothers - Times of India
If you win, what will you make them do?
33- Beach or Mountains? Or is there another place to like better?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
49~ How many times have you been married? Why did they end?
What is your favorite toy? Ever wanted to try a specific toy?
12- What’s your favorite food? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
1~ How old were you when you had your first kiss? Who? Care to Share?
3- What Superhero or Superpower would you want to be/have?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
11- How about if they like a certain sports team? 12-How about drinking too much?
34- Ever been to a concert? What was your favorite? Who would you like to see?
10~ How many dates are necessary before you to have sex with someone?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Doctor/Nurse Stripper/Client
37- Do you like your name? If you could change it, what would you change it too?
Prisoner/Prison Guard Landlord/Tenant
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
9~ How many times over your lifetime do you think you have had sex so far?
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?
Get this wrong and this could mean the end… :-) some funny, some not…
12- What is the weirdest thing you've ever eaten?
82~ Do you have any fantasies involving Role-Playing?
14- What is an embarrassing moment in your life? How about your most embarrassing?
* Give a rating for each one (0-100)
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?
50~ How many children do you have? What are their ages?
28~ What are some things that turn on? What is your biggest turn on?
19- Do/have you smoked? What do you prefer? How often?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Have you ever? Care to Share?
10- What is your favorite family tradition? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7-What do I do in bed that drives you wild? How about, what turns you off?
89~ Do you like taking showers together?
40~ What’s the weirdest place you’ve ever had sex?
What is your favorite position? Why?
*** Random Questions ***
80~ Share your top three fantasies/desires. (Be detailed) 😊
21- What's your favorite way to spend a weekend or time off?
32- What's your greatest talent? Can I see it right now?
53~ How much can you tell me about the one thing you are most passionate about?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
47~ What would be your dream job and why?
How about if they talk dirty and/or call you names?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Master/Slave Boss/Maid
36~ What is your favorite time of day to have sex/make love?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
92~ Everyone needs a “safe” word. What is yours?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Any that are a turn off?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
17- Have you ever done drugs? Which ones? How often?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Would /have you ever given your partner a lap dance and Striptease?
31- If given a chance to be immortal, would you take it? Why?
23- What is your dream job? What was it as a child?
27- What was/ is nickname? Does it have a meaning behind it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
62~ Have you used adult toys?
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…
What have you learned about me that was new and/or surprising?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
60~ How important is oral sex? Do you like receiving? Do you like giving?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
84~ How do you feel about reading/listening to adult stories?
52~ What are your hobbies?
13- What is the craziest/scariest thing you've ever done?
*** What’s Your Favorite…? ***
10- List 5 of your top pet peeves.
92~ Have you ever had or have an STD? How many? What was it?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5~ When you first started having sex, was it what you thought it would be?
18- How often do you drink alcohol? What is your favorite drink?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
13- How about having a certain hair cut/style?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
51~ Are you willing to play adult games with your partner?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
The Ice Breaker Questions
71~ Would you give your partner a hand or foot job? Would you receive one?
You know that I will be 100% truthful, so ask.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
13~ Is there a difference between, making love, having sex, and fucking?
48~ Have you ever paid or been paid for sex?
That one or two things that made you go hmmmm, OMG or wow!
Escort/Client Job Applicant/Hiring Manager
11- What's your favorite restaurant? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
How well do you know me? And some of your thoughts about me
Over time has your thoughts on sex changed?
13- What’s your favorite drink? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
What have you learned about yourself that you did not before this?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
65~ Describe the best orgasm you’ve ever had? Care to share?
15- What bad habit do you wish you could quit? Do you have any addictions?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What is your view on sex? Meaning, When/Where/ How often/
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
48~ Do you have any siblings? Are you close to your family?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Do you watch it? What is your favorite?
What was the longest? What was the shortest?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
If yes, what?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
46~ Have you ever used furniture, or other types of things to aid you while having sex?
1- What was your first impression of me? Has it changed?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
26~ What side of the bed do you sleep on?
9- What’s your favorite season and why? What’s your least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
4- For a pet, Cat, dog or other?
14- What's your favorite dessert? Do you a least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
How old are you? Male or Female?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Family Relation Age Play
How many partners have you had oral sex with? Who? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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…
15- What's your favorite saying? What word or phrase is your least favorite?
Do you think this brought you closer together?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Would you read them together?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
*** Deal Breaker Questions ***
19~ Who/when was your first “heartbreak”?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
I would allow you to do it… What would you do to me?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Any that are a turn off?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
76~ Have you had a threesome? Care to Share?
Nurse/Patient Celebrity/Fan
8- What's your favorite flavor of ice cream? Do you a least favorite?
34~ Do you like the lights on or off during sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
44~ Care to share something about yourself that no one else knows about you?
7- What are your thoughts on religion? Is there an afterlife?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
29- How superstitious are you?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
If YES, was it with 2 men or 2 women? Did you enjoy it?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
5- Have you ever been hypnotized? Would you allow yourself to be?
What do you dislike about me? I asked you to be 100% honest.
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
81~ Do you have any kinks and/or fetishes?
28- What are some things that people do that irritate you?
70~ Would/do you have/like anal sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
1- What’s your favorite animal? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
39~ What are your love languages?
52~ Are you willing to make “those types” of bets with your partner?
30~ What's something unexpected that turns you on?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
22- What is your favorite childhood memory? What is your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
2- What’s your favorite color? Do you a least favorite?
Does the thought excite you? Care to share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
9- If you could have three wishes, what would they be? Why?
Do you have a favorite? Is it ok if your partner does?
Nothing too Serious
What would you say to prove to yourself that it was really you?
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?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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)
19- What’s your favorite fairytale? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
42~ What’s your biggest regret in life?
If NO, would you ever have one? Would it be with 2 men or 2 women?
38~ Share your most embarrassing sexual memory?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
7- What if a person smells a certain way? 8- How about smoking?
11- List at least 5 things on your bucket list. Have you done any of them already?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Do you like the “69” position? Do you prefer to be on top or bottom?
*** Questions about Relationships/Past ***
Model/Photographer Police/Criminal
33- If you could visit any time period, when would you pick? Please explain why?
How many times do you think you have “made love”?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you mind if your partner watched it? How about together vs alone?
11~ Have you ever been caught by your parents or children or others while having sex?
3- What’s your favorite smell? Do you a least favorite?
51~ What tends to bring a smile to your face?
18~ Who/when was your first “crush”?
3- Should Pluto still be considered a planet? 4- How about smoking?