What is the most interesting question you can ask to get to know someone?
Last Updated: 03.07.2025 01:53
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
3- What’s your favorite smell? Do you a least favorite?
20- What’s your favorite candy? What’s your least favorite?
Anthropic’s Claude AI became a terrible business owner in experiment that got ‘weird’ - TechCrunch
Model/Photographer Police/Criminal
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
Shemar Stewart Calls Out Bengals Front Office As Contract Clash Continues - Sports Illustrated
What have you learned about me that was new and/or surprising?
36~ What is your favorite time of day to have sex/make love?
82~ Do you have any fantasies involving Role-Playing?
More on Apple’s Trust-Eroding ‘F1 The Movie’ Wallet Ad - Daring Fireball
34- Ever been to a concert? What was your favorite? Who would you like to see?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
Are fanservice-y characters (i.e. Lara Croft, Tifa Lockhart) immediately bad?
83~ How do you feel about Porn?
51~ What tends to bring a smile to your face?
50~ How many children do you have? What are their ages?
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3- What was the most surprising thing you’ve learned about me throughout our relationship?
Teacher/Student Stranger/One Night Stand
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How can we get rid of viral fever naturaly?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
17- What’s your favorite holiday? What’s your least favorite?
Rod Stewart at Glastonbury: Old school charm from another era - BBC
Would you ever want to be woken up with oral and/or intercourse?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
53~ How much can you tell me about the one thing you are most passionate about?
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10~ How many dates are necessary before you to have sex with someone?
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?
Secret leprosy infected the Americas before European arrival - DW
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
22- What is your favorite childhood memory? What is your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
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14- What is an embarrassing moment in your life? How about your most embarrassing?
The Ice Breaker Questions
67~ Do you like it when your partner moans and/or is vocal during sex?
MLB investigating abuse claims from Giants pitcher’s wife - KRON4
*** Deal Breaker Questions ***
What is your favorite position? Why?
How well do you know me? And some of your thoughts about me
‘Stick’: Apple’s Golf Comedy Scores on the Charms of Owen Wilson - Rolling Stone
Doctor/Nurse Stripper/Client
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you like it when they show and tell you what they want?
If you say it, I will stop, and we can talk about it when you are ready.
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
10- What is your favorite family tradition? What’s your least favorite?
What was the longest? What was the shortest?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
60~ How important is oral sex? Do you like receiving? Do you like giving?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
52~ Are you willing to make “those types” of bets with your partner?
What is your view on sex? Meaning, When/Where/ How often/
34~ Do you like the lights on or off during sex?
81~ Do you have any kinks and/or fetishes?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
3- What Superhero or Superpower would you want to be/have?
84~ How do you feel about reading/listening to adult stories?
15~ Have you ever been “in love”? Who? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
80~ Share your top three fantasies/desires. (Be detailed) 😊
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
12- What’s your favorite food? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
19~ Who/when was your first “heartbreak”?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If you win, what will you make them do?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
19- Do/have you smoked? What do you prefer? How often?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you think this brought you closer together?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
*** Questions about Relationships/Past ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
18~ Who/when was your first “crush”?
47~ What would be your dream job and why?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
33- Beach or Mountains? Or is there another place to like better?
11- List at least 5 things on your bucket list. Have you done any of them already?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
9- What’s your favorite season and why? What’s your least favorite?
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)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
7- What are your thoughts on religion? Is there an afterlife?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
70~ Would/do you have/like anal sex?
5~ When you first started having sex, was it what you thought it would be?
1- What was your first impression of me? Has it changed?
18- How often do you drink alcohol? What is your favorite drink?
49~ How many times have you been married? Why did they end?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Prisoner/Prison Guard Landlord/Tenant
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Nurse/Patient Celebrity/Fan
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
38~ Share your most embarrassing sexual memory?
*** Random Questions ***
1- What’s your favorite animal? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
You know that I will be 100% truthful, so ask.
What would you say to prove to yourself that it was really you?
2- What’s your favorite color? Do you a least favorite?
12- What is the weirdest thing you've ever eaten?
42~ Ever been spanked during sex? Did you like it? Would you like me to do 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,
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
6- Do you have dreams? Can you remember them? What do you usually dream about?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Get this wrong and this could mean the end… :-) some funny, some not…
21~ What was the best date you ever went on? What has been the worst?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
26~ What side of the bed do you sleep on?
11- What's your favorite restaurant? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
28~ What are some things that turn on? What is your biggest turn on?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
33- If you could visit any time period, when would you pick? Please explain why?
If NO, would you ever have one? Would it be with 2 men or 2 women?
89~ Do you like taking showers together?
7- What if a person smells a certain way? 8- How about smoking?
61~ How willing would you be to try new sexual positions?
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’s the longest time you gone without having sex, after, having it? How much time between the others?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
I would allow you to do it… What would you do to me?
17- Have you ever done drugs? Which ones? How often?
How many partners have you had oral sex with? Who? Care to Share?
Would you read them together?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
42~ What’s your biggest regret in life?
15- What bad habit do you wish you could quit? Do you have any addictions?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
29- How superstitious are you?
13- What’s your favorite drink? What’s your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
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?
76~ Have you had a threesome? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
*** Questions About Me ***
65~ Describe the best orgasm you’ve ever had? Care to share?
Does the thought excite you? Care to share?
51~ Are you willing to play adult games with your partner?
31- If given a chance to be immortal, would you take it? Why?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How old are you? Male or Female?
(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…)
Family Relation Age Play
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
92~ Have you ever had or have an STD? How many? What was it?
10- List 5 of your top pet peeves.
Have you ever? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you watch it? What is your favorite?
Master/Slave Boss/Maid
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Any that are a turn off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
48~ Do you have any siblings? Are you close to your family?
30~ What's something unexpected that turns you on?
Do you like the “69” position? Do you prefer to be on top or bottom?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
23- What is your dream job? What was it as a child?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave 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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
32- What's your greatest talent? Can I see it right now?
14- What's your favorite dessert? Do you a least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Nothing too Serious
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What have you learned about yourself that you did not before this?
Any that are a turn off?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
19- What’s your favorite fairytale? What’s your least favorite?
What do you dislike about me? I asked you to be 100% honest.
Repairman/Lonely Wife Virgin/Experienced
11- How about if they like a certain sports team? 12-How about drinking too much?
Over time has your thoughts on sex changed?
Do you have a favorite? Is it ok if your partner does?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
If yes, what?
36- Do you play video games? What is your favorite? Do you a least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
How about if they talk dirty and/or call you names?
Would you allow me to clean every part of your body with my soapy hands and fingers?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
15- What's your favorite saying? What word or phrase is your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
39~ What are your love languages?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
21- What's your favorite way to spend a weekend or time off?
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
44~ Care to share something about yourself that no one else knows about you?
*** What’s Your Favorite…? ***
92~ Everyone needs a “safe” word. What is yours?
13- What is the craziest/scariest thing you've ever done?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
8- What's your favorite flavor of ice cream? Do you a least favorite?
62~ Have you used adult toys?
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?
13- How about having a certain hair cut/style?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
5- Have you ever been hypnotized? Would you allow yourself to be?
4- For a pet, Cat, dog or other?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
8- What are your thoughts on politics?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
9- Is there something you’ve always wanted to ask me but you’re afraid?
48~ Have you ever paid or been paid for sex?
How many times do you think you have “made love”?
52~ What are your hobbies?
Please share Did you stop?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
* Give a rating for each one (0-100)
Would you do it again, and would you rather 2 females or 2 males?
Would /have you ever given your partner a lap dance and Striptease?
Can you Deep Throat? Do you like the taste of yourself?
25~ How do you feel about PDA? (Public Display of Affection)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
11~ Have you ever been caught by your parents or children or others while having sex?
22- Do you have any birth marks? How about scars? Care to share how you got them?
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…
Escort/Client Job Applicant/Hiring Manager
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
28- What are some things that people do that irritate you?
37- Do you like your name? If you could change it, what would you change it too?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
9- If you could have three wishes, what would they be? Why?
What is your favorite toy? Ever wanted to try a specific toy?
40~ What’s the weirdest place you’ve ever had sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
45~ How do you feel about me blindfolding you? How about blindfolding me?