What is the most interesting question you can ask to get to know someone?
08.06.2025 06:24
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
52~ What are your hobbies?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
I gave Google’s AI Mode a shot, but I’m still sticking with Perplexity - Android Authority
What have you learned about me that was new and/or surprising?
13- What is the craziest/scariest thing you've ever done?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
What is one thing nice you did for someone today or something they did for you?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Do you watch it? What is your 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)
When does a woman know she is cumming?
7- What if a person smells a certain way? 8- How about smoking?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13- How about having a certain hair cut/style?
Southwest Floats First Class, Lounges, Long Haul Flying: Good Strategy? - One Mile at a Time
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
19- What’s your favorite fairytale? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
How is digital marketing important for business?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
38~ Share your most embarrassing sexual memory?
Six Types Of Dinosaur Eggs Found In One Place - The Daily Galaxy
What is your favorite toy? Ever wanted to try a specific toy?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
How many partners have you had oral sex with? Who? Care to Share?
Is Matt Gaetz qualified to be Attorney General of the United States?
Doctor/Nurse Stripper/Client
9~ How many times over your lifetime do you think you have had sex so far?
What is your favorite position? Why?
At what stage in your life did you realize, "No, I can't do this any more" and walk out? Why?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
8- What are your thoughts on politics?
15- What bad habit do you wish you could quit? Do you have any addictions?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What have you learned about yourself that you did not before this?
65~ Describe the best orgasm you’ve ever had? Care to share?
Will you share your wife? Can she take both of us at the same time?
28- What are some things that people do that irritate you?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Walking This Many Steps Per Day Can Cut Your Risk Of Early Death - HuffPost
44~ Care to share something about yourself that no one else knows about you?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What is your view on sex? Meaning, When/Where/ How often/
Why did the American's mulberry harbor not hold up after D-Day?
5- Have you ever been hypnotized? Would you allow yourself to be?
21~ What was the best date you ever went on? What has been the worst?
Escort/Client Job Applicant/Hiring Manager
Which Bibles can one read and be confident they are reading the inerrant word of God?
15- What's your favorite saying? What word or phrase is your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
4- For a pet, Cat, dog or other?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
27- What was/ is nickname? Does it have a meaning behind it?
70~ Would/do you have/like anal sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Does the thought excite you? Care to share?
31- If given a chance to be immortal, would you take it? Why?
Model/Photographer Police/Criminal
51~ What tends to bring a smile to your face?
76~ Have you had a threesome? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
20- What’s your favorite candy? What’s your least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
1~ How old were you when you had your first kiss? Who? Care to Share?
*** Questions About Me ***
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What would you say to prove to yourself that it was really you?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How old are you? Male or Female?
*** Questions about Relationships/Past ***
49~ How many times have you been married? Why did they end?
3- What Superhero or Superpower would you want to be/have?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
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?
1- What’s your favorite animal? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
25~ How do you feel about PDA? (Public Display of Affection)
Any that are a turn off?
Can you Deep Throat? Do you like the taste of yourself?
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,
Please share Did you stop?
13- What’s your favorite drink? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
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…
Would you allow me to clean every part of your body with my soapy hands and fingers?
11- What's your favorite restaurant? What’s your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
6- Do you have dreams? Can you remember them? What do you usually dream about?
(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…)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
7- What are your thoughts on religion? Is there an afterlife?
3- Should Pluto still be considered a planet? 4- How about smoking?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Nurse/Patient Celebrity/Fan
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?
89~ Do you like taking showers together?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
*** Deal Breaker Questions ***
I would allow you to do it… What would you do to me?
9- What’s your favorite season and why? What’s your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
Family Relation Age Play
3- What’s your favorite smell? Do you a least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
82~ Do you have any fantasies involving Role-Playing?
Would /have you ever given your partner a lap dance and Striptease?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
11- List at least 5 things on your bucket list. Have you done any of them already?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
92~ Have you ever had or have an STD? How many? What was it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
10~ How many dates are necessary before you to have sex with someone?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Would you read them together?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Do you like it when they show and tell you what they want?
If NO, would you ever have one? Would it be with 2 men or 2 women?
The Ice Breaker Questions
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
22- Do you have any birth marks? How about scars? Care to share how you got them?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
48~ Have you ever paid or been paid for sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
53~ How much can you tell me about the one thing you are most passionate about?
60~ How important is oral sex? Do you like receiving? Do you like giving?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How about if they talk dirty and/or call you names?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
26~ What side of the bed do you sleep on?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
64~ When was your very first orgasm? When was your first from having sex? Care to share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
84~ How do you feel about reading/listening to adult stories?
34- Ever been to a concert? What was your favorite? Who would you like to see?
23- What is your dream job? What was it as a child?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
71~ Would you give your partner a hand or foot job? Would you receive one?
17- Have you ever done drugs? Which ones? How often?
Get this wrong and this could mean the end… :-) some funny, some not…
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
29- How superstitious are you?
14- What's your favorite dessert? Do you a least favorite?
*** Random Questions ***
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
10- List 5 of your top pet peeves.
2- What’s your favorite color? Do you a least favorite?
Would you do it again, and would you rather 2 females or 2 males?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
51~ Are you willing to play adult games with your partner?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
If yes, what?
How many times do you think you have “made love”?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Any that are a turn off?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
13~ Is there a difference between, making love, having sex, and fucking?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
37- Do you like your name? If you could change it, what would you change it too?
81~ Do you have any kinks and/or fetishes?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
67~ Do you like it when your partner moans and/or is vocal during sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If YES, was it with 2 men or 2 women? Did you enjoy it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
42~ What’s your biggest regret in life?
You know that I will be 100% truthful, so ask.
Would you ever want to be woken up with oral and/or intercourse?
39~ What are your love languages?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
30~ What's something unexpected that turns you on?
Do you think this brought you closer together?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
11- How about if they like a certain sports team? 12-How about drinking too much?
12- What’s your favorite food? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
19- Do/have you smoked? What do you prefer? How often?
9- If you could have three wishes, what would they be? Why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
10- What is your favorite family tradition? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
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?
Do you have a favorite? Is it ok if your partner does?
How well do you know me? And some of your thoughts about me
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
33- Beach or Mountains? Or is there another place to like better?
36- Do you play video games? What is your favorite? Do you a least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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?
Have you ever? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
12- What is the weirdest thing you've ever eaten?
18- How often do you drink alcohol? What is your favorite drink?
22- What is your favorite childhood memory? What is your least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
50~ How many children do you have? What are their ages?
15~ Have you ever been “in love”? Who? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
11~ Have you ever been caught by your parents or children or others while having sex?
32- What's your greatest talent? Can I see it right now?
52~ Are you willing to make “those types” of bets with your partner?
48~ Do you have any siblings? Are you close to your family?
19~ Who/when was your first “heartbreak”?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
62~ Have you used adult toys?
34~ Do you like the lights on or off during sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
If you win, what will you make them do?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
40~ What’s the weirdest place you’ve ever had sex?
Nothing too Serious
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
*** What’s Your Favorite…? ***
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Master/Slave Boss/Maid
17- What’s your favorite holiday? What’s your least favorite?
Over time has your thoughts on sex changed?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
What was the longest? What was the shortest?
Would you mind if your partner watched it? How about together vs alone?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Teacher/Student Stranger/One Night Stand
61~ How willing would you be to try new sexual positions?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
83~ How do you feel about Porn?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
47~ What would be your dream job and why?
What do you dislike about me? I asked you to be 100% honest.
* Give a rating for each one (0-100)
If you say it, I will stop, and we can talk about it when you are ready.
18~ Who/when was your first “crush”?
5~ When you first started having sex, was it what you thought it would be?
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…
1- What was your first impression of me? Has it changed?