What is the most interesting question you can ask to get to know someone?
12.06.2025 12:21
Prisoner/Prison Guard Landlord/Tenant
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Has a cop ever said something to you which was completely unexpected?
You know that I will be 100% truthful, so ask.
17- What’s your favorite holiday? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
NASA Switches to Backup Fuel Line After Psyche Thruster Glitch - Gizmodo
52~ Are you willing to make “those types” of bets with your partner?
What is your view on sex? Meaning, When/Where/ How often/
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
New study finds strong link between hearing loss and dementia - WKRC
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Family Relation Age Play
Would /have you ever given your partner a lap dance and Striptease?
How old are you? Male or Female?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
NASA is already great. Right now. - NASA Watch
33- If you could visit any time period, when would you pick? Please explain why?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
32- What's your greatest talent? Can I see it right now?
71~ Would you give your partner a hand or foot job? Would you receive one?
21- What's your favorite way to spend a weekend or time off?
Charting the Global Economy: US GDP Falls on Larger Trade Hit - Bloomberg
13- What’s your favorite drink? What’s your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Trump Crypto Wallet Goes Dark Following Cease and Desist - Decrypt
Do you shave/trim your pubic hair? For you guys do you shave your balls?
48~ Do you have any siblings? Are you close to your family?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
10~ How many dates are necessary before you to have sex with someone?
47~ What would be your dream job and why?
13~ Is there a difference between, making love, having sex, and fucking?
Baby saved by gene-editing therapy 'graduates' from hospital, goes home - ABC News
Please share Did you stop?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
*** Random Questions ***
Live Updates From Apple WWDC 2025 🔴 - Gizmodo
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
11~ Have you ever been caught by your parents or children or others while having sex?
61~ How willing would you be to try new sexual positions?
Would you read them together?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Report: Steelers, Dolphins renew talks about a trade for Jonnu Smith - NBC Sports
31- If given a chance to be immortal, would you take it? Why?
Do you like it when they show and tell you what they want?
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?
Why do men say women hit the wall at 24?
1- What was your first impression of me? Has it changed?
Does the thought excite you? Care to share?
If yes, what?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would you mind if your partner watched it? How about together vs alone?
What is your favorite toy? Ever wanted to try a specific toy?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
65~ Describe the best orgasm you’ve ever had? Care to share?
13- How about having a certain hair cut/style?
What would you say to prove to yourself that it was really you?
That one or two things that made you go hmmmm, OMG or wow!
42~ What’s your biggest regret in life?
* 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…)
I would allow you to do it… What would you do to me?
37- Do you like your name? If you could change it, what would you change it too?
Would you allow me to clean every part of your body with my soapy hands and fingers?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
If you win, what will you make them do?
60~ How important is oral sex? Do you like receiving? Do you like giving?
7-What do I do in bed that drives you wild? How about, what turns you off?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
5- Have you ever been hypnotized? Would you allow yourself to be?
1~ How old were you when you had your first kiss? Who? Care to Share?
*** Deal Breaker Questions ***
51~ Are you willing to play adult games with your partner?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What is your favorite position? Why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
*** What’s Your Favorite…? ***
2- What’s your favorite color? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Doctor/Nurse Stripper/Client
What do you dislike about me? I asked you to be 100% honest.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you watch it? What is your favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
26~ What side of the bed do you sleep on?
8- What are your thoughts on politics?
10- What is your favorite family tradition? What’s your least favorite?
Do you think this brought you closer together?
*** Questions About Me ***
83~ How do you feel about Porn?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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…
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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?
15~ Have you ever been “in love”? Who? Care to Share?
What have you learned about me that was new and/or surprising?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
9~ How many times over your lifetime do you think you have had sex so far?
5~ When you first started having sex, was it what you thought it would be?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
40~ What’s the weirdest place you’ve ever had sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If NO, would you ever have one? Would it be with 2 men or 2 women?
23- What is your dream job? What was it as a child?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
9- What’s your favorite season and why? What’s your least favorite?
82~ Do you have any fantasies involving Role-Playing?
If YES, was it with 2 men or 2 women? Did you enjoy it?
3- What Superhero or Superpower would you want to be/have?
51~ What tends to bring a smile to your face?
11- What's your favorite restaurant? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
92~ Everyone needs a “safe” word. What is yours?
30~ What's something unexpected that turns you on?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
12- What’s your favorite food? What’s your least favorite?
62~ Have you used adult toys?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
76~ Have you had a threesome? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Any that are a turn off?
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,
Model/Photographer Police/Criminal
29~ What are some things that turn you off? What is your biggest turn off?
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?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
The Ice Breaker Questions
16~ Do you believe in “soulmates”? Have you found yours? 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?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
33- Beach or Mountains? Or is there another place to like better?
20- What’s your favorite candy? What’s your least favorite?
14- What's your favorite dessert? Do you a least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Repairman/Lonely Wife Virgin/Experienced
4- For a pet, Cat, dog or other?
36~ What is your favorite time of day to have sex/make love?
27- What was/ is nickname? Does it have a meaning behind it?
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?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
24~ What are your expectations in a relationship? (I know a very big question, take your time)
29- How superstitious are you?
Teacher/Student Stranger/One Night Stand
19- Do/have you smoked? What do you prefer? How often?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
How many partners have you had oral sex with? Who? Care to Share?
How about if they talk dirty and/or call you names?
38~ Share your most embarrassing sexual memory?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7- What are your thoughts on religion? Is there an afterlife?
Nurse/Patient Celebrity/Fan
28~ What are some things that turn on? What is your biggest turn on?
Nothing too Serious
10- List 5 of your top pet peeves.
52~ What are your hobbies?
3- What’s your favorite smell? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
67~ Do you like it when your partner moans and/or is vocal during sex?
How well do you know me? And some of your thoughts about me
80~ Share your top three fantasies/desires. (Be detailed) 😊
15- What's your favorite saying? What word or phrase is your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
36- Do you play video games? What is your favorite? Do you a least favorite?
89~ Do you like taking showers together?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Have you ever? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
49~ How many times have you been married? Why did they end?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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…
Would you do it again, and would you rather 2 females or 2 males?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
18~ Who/when was your first “crush”?
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)
Master/Slave Boss/Maid
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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?
9- If you could have three wishes, what would they be? Why?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
70~ Would/do you have/like anal sex?
19~ Who/when was your first “heartbreak”?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
3- Should Pluto still be considered a planet? 4- How about smoking?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
13- What is the craziest/scariest thing you've ever done?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
18- How often do you drink alcohol? What is your favorite drink?
How many times do you think you have “made love”?
81~ Do you have any kinks and/or fetishes?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Get this wrong and this could mean the end… :-) some funny, some not…
Will you cheat again? How can, you be sure? Define what cheating is to you.
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
Over time has your thoughts on sex changed?
What have you learned about yourself that you did not before this?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What was the longest? What was the shortest?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
39~ What are your love languages?
7- What if a person smells a certain way? 8- How about smoking?
28- What are some things that people do that irritate you?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
44~ Care to share something about yourself that no one else knows about you?
Any that are a turn off?
Can you Deep Throat? Do you like the taste of yourself?
11- How about if they like a certain sports team? 12-How about drinking too much?
25~ How do you feel about PDA? (Public Display of Affection)
50~ How many children do you have? What are their ages?
34~ Do you like the lights on or off during sex?
Do you have a favorite? Is it ok if your partner does?
34- Ever been to a concert? What was your favorite? Who would you like to see?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** Questions about Relationships/Past ***
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
48~ Have you ever paid or been paid for sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
22- What is your favorite childhood memory? What is your least favorite?
12- What is the weirdest thing you've ever eaten?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.