What is the most interesting question you can ask to get to know someone?
11.06.2025 02:31
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
If yes, what?
8- What are your thoughts on politics?
Evidence piles up that Trump's tariffs are crushing job market - Daily Kos
If YES, was it with 2 men or 2 women? Did you enjoy it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
15~ Have you ever been “in love”? Who? Care to Share?
Drug deaths plummet among young Americans as fentanyl carnage eases - NPR
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
The Ice Breaker Questions
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Get this wrong and this could mean the end… :-) some funny, some not…
34- Ever been to a concert? What was your favorite? Who would you like to see?
76~ Have you had a threesome? Care to Share?
Review: At $349, AMD’s 16GB Radeon RX 9060 XT is the new midrange GPU to beat - Ars Technica
*** Deal Breaker Questions ***
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
8- What's your favorite flavor of ice cream? Do you a least favorite?
SpaceX launches Starlink satellites to orbit on 70th Falcon 9 flight of the year (photos) - Space
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Why do companies cull employees during financial downturns without saying so?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
39~ What are your love languages?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
3- What’s your favorite smell? Do you a least favorite?
18~ Who/when was your first “crush”?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
What Happened at Pitchfork’s Zine Launch With Turnstile - Pitchfork
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
13- How about having a certain hair cut/style?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
10-year Treasury yield rises ahead of key jobs report - CNBC
29- How superstitious are you?
3- Should Pluto still be considered a planet? 4- How about smoking?
Doctor/Nurse Stripper/Client
Fireball streaks through aurora-filled skies photo of the day for June 5, 2025 - Space
Does the thought excite you? Care to share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Asteroid Larger Than Golden Gate Bridge Approaches Earth In Rare Event - Forbes
7-What do I do in bed that drives you wild? How about, what turns you off?
19- Do/have you smoked? What do you prefer? How often?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
14- What is an embarrassing moment in your life? How about your most embarrassing?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
37- Do you like your name? If you could change it, what would you change it too?
Escort/Client Job Applicant/Hiring Manager
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
10~ How many dates are necessary before you to have sex with someone?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
22- What is your favorite childhood memory? What is your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
81~ Do you have any kinks and/or fetishes?
11- What's your favorite restaurant? What’s your least favorite?
34~ Do you like the lights on or off during sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
21~ What was the best date you ever went on? What has been the worst?
7- What are your thoughts on religion? Is there an afterlife?
1- What was your first impression of me? Has it changed?
Do you like it when they show and tell you what they want?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you ever want to be woken up with oral and/or intercourse?
Please share Did you stop?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
5- Have you ever been hypnotized? Would you allow yourself to be?
Master/Slave Boss/Maid
Family Relation Age Play
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
48~ Have you ever paid or been paid for sex?
26~ What side of the bed do you sleep on?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
10- What is your favorite family tradition? What’s your least favorite?
*** What’s Your Favorite…? ***
13- What is the craziest/scariest thing you've ever done?
52~ What are your hobbies?
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?
That one or two things that made you go hmmmm, OMG or wow!
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How about if they talk dirty and/or call you names?
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…
46~ Have you ever used furniture, or other types of things to aid you while having sex?
27- What was/ is nickname? Does it have a meaning behind it?
*** Questions About Me ***
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
You know that I will be 100% truthful, so ask.
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What have you learned about yourself that you did not before this?
Nurse/Patient Celebrity/Fan
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
17- What’s your favorite holiday? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
1- What’s your favorite animal? Do you a least favorite?
What is your favorite position? Why?
How many times do you think you have “made love”?
13~ Is there a difference between, making love, having sex, and fucking?
42~ What’s your biggest regret in life?
19- What’s your favorite fairytale? What’s your least favorite?
I would allow you to do it… What would you do to me?
*** Questions about Relationships/Past ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
4- For a pet, Cat, dog or other?
33- Beach or Mountains? Or is there another place to like better?
14- What's your favorite dessert? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
70~ Would/do you have/like anal sex?
15- What's your favorite saying? What word or phrase is your least favorite?
What is your view on sex? Meaning, When/Where/ How often/
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)
53~ How much can you tell me about the one thing you are most passionate about?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
92~ Have you ever had or have an STD? How many? What was it?
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,
Would you do it again, and would you rather 2 females or 2 males?
51~ Are you willing to play adult games with your partner?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Would /have you ever given your partner a lap dance and Striptease?
9- If you could have three wishes, what would they be? Why?
If you say it, I will stop, and we can talk about it when you are ready.
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
49~ How many times have you been married? Why did they end?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
40~ What’s the weirdest place you’ve ever had sex?
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?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
11- List at least 5 things on your bucket list. Have you done any of them already?
62~ Have you used adult toys?
22- Do you have any birth marks? How about scars? Care to share how you got them?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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…
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
19~ Who/when was your first “heartbreak”?
12- What’s your favorite food? What’s your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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?
47~ What would be your dream job and why?
Have you ever? Care to Share?
What was the longest? What was the shortest?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Nothing too Serious
30~ What's something unexpected that turns you on?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Do you think this brought you closer together?
65~ Describe the best orgasm you’ve ever had? Care to share?
33- If you could visit any time period, when would you pick? Please explain why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
89~ Do you like taking showers together?
If you win, what will you make them do?
Would you allow me to clean every part of your body with my soapy hands and fingers?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you like the “69” position? Do you prefer to be on top or bottom?
2- What’s your favorite color? Do you a 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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
92~ Everyone needs a “safe” word. What is yours?
What would you say to prove to yourself that it was really you?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
50~ How many children do you have? What are their ages?
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?
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?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
83~ How do you feel about Porn?
51~ What tends to bring a smile to your face?
3- What Superhero or Superpower would you want to be/have?
9- What’s your favorite season and why? What’s your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would you mind if your partner watched it? How about together vs alone?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
*** Random Questions ***
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Repairman/Lonely Wife Virgin/Experienced
How well do you know me? And some of your thoughts about me
67~ Do you like it when your partner moans and/or is vocal during sex?
How many partners have you had oral sex with? Who? Care to Share?
Do you watch it? What is your favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
29~ What are some things that turn you off? What is your biggest turn off?
Teacher/Student Stranger/One Night Stand
Over time has your thoughts on sex changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
17- Have you ever done drugs? Which ones? How often?
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?
9~ How many times over your lifetime do you think you have had sex so far?
20- What’s your favorite candy? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
Any that are a turn off?
If NO, would you ever have one? Would it be with 2 men or 2 women?
82~ Do you have any fantasies involving Role-Playing?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would you read them together?
21- What's your favorite way to spend a weekend or time off?
1~ How old were you when you had your first kiss? Who? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
10- List 5 of your top pet peeves.
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
80~ Share your top three fantasies/desires. (Be detailed) 😊
How old are you? Male or Female?
Do you have a favorite? Is it ok if your partner does?
61~ How willing would you be to try new sexual positions?
48~ Do you have any siblings? Are you close to your family?
Is it ok for a man to perform oral sex after he has ejaculated inside of 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?
13- What’s your favorite drink? What’s your least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
49~ If you could, would you want to be the opposite sex for a day, week, or year?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Can you Deep Throat? Do you like the taste of yourself?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
12- What is the weirdest thing you've ever eaten?
Model/Photographer Police/Criminal
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
11- How about if they like a certain sports team? 12-How about drinking too much?
Any that are a turn off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
71~ Would you give your partner a hand or foot job? Would you receive one?
23- What is your dream job? What was it as a child?
31- If given a chance to be immortal, would you take it? Why?
What do you dislike about me? I asked you to be 100% honest.
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
32- What's your greatest talent? Can I see it right now?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
45~ How do you feel about me blindfolding you? How about blindfolding me?
28- What are some things that people do that irritate you?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
5~ When you first started having sex, was it what you thought it would be?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Will you cheat again? How can, you be sure? Define what cheating is to you.
36~ What is your favorite time of day to have sex/make love?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Prisoner/Prison Guard Landlord/Tenant
What have you learned about me that was new and/or surprising?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
7- What if a person smells a certain way? 8- How about smoking?
38~ Share your most embarrassing sexual memory?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
* Give a rating for each one (0-100)
(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…)
44~ Care to share something about yourself that no one else knows about you?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?