What is the most interesting question you can ask to get to know someone?
11.06.2025 01:53
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Escort/Client Job Applicant/Hiring Manager
4- For a pet, Cat, dog or other?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- Should Pluto still be considered a planet? 4- How about smoking?
I gave Google’s AI Mode a shot, but I’m still sticking with Perplexity - Android Authority
23- What is your dream job? What was it as a child?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Over time has your thoughts on sex changed?
11- List at least 5 things on your bucket list. Have you done any of them already?
We finally may be able to rid the world of mosquitoes. But should we? - The Washington Post
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
44~ Care to share something about yourself that no one else knows about you?
10- What is your favorite family tradition? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
89~ Do you like taking showers together?
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…
Who is someone that inspires you?
82~ Do you have any fantasies involving Role-Playing?
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?
7- What are your thoughts on religion? Is there an afterlife?
Why is blood sugar ranging from 70-180 in a day and checked through a glucometer?
14- What is an embarrassing moment in your life? How about your most embarrassing?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Popular chicken chain shares, massive expansion plan - TheStreet
11- How about if they like a certain sports team? 12-How about drinking too much?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
If yes, what?
Can we state Alia Bhatt as the most versatile actress in Bollywood now?
9- Is there something you’ve always wanted to ask me but you’re afraid?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
How many times do you think you have “made love”?
Why does my crush make me jealous about having a girlfriend?
81~ Do you have any kinks and/or fetishes?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
13- What is the craziest/scariest thing you've ever done?
What was the worst spanking you got growing up?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Family Relation Age Play
7- What if a person smells a certain way? 8- How about smoking?
(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…)
If NO, would you ever have one? Would it be with 2 men or 2 women?
52~ What are your hobbies?
Please share Did you stop?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
9- What’s your favorite season and why? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
9~ How many times over your lifetime do you think you have had sex so far?
25~ How do you feel about PDA? (Public Display of Affection)
18- How often do you drink alcohol? What is your favorite drink?
33- If you could visit any time period, when would you pick? Please explain why?
Repairman/Lonely Wife Virgin/Experienced
9- If you could have three wishes, what would they be? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
19- What’s your favorite fairytale? 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)
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
33- Beach or Mountains? Or is there another place to like better?
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?
53~ How much can you tell me about the one thing you are most passionate about?
45~ How do you feel about me blindfolding you? How about blindfolding me?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Would you read them together?
20- What’s your favorite candy? What’s your least favorite?
13- How about having a certain hair cut/style?
Would /have you ever given your partner a lap dance and Striptease?
Prisoner/Prison Guard Landlord/Tenant
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Doctor/Nurse Stripper/Client
51~ Are you willing to play adult games with your partner?
11~ Have you ever been caught by your parents or children or others while having sex?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
That one or two things that made you go hmmmm, OMG or wow!
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
29~ What are some things that turn you off? What is your biggest turn off?
Do you think this brought you closer together?
70~ Would/do you have/like anal sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
34~ Do you like the lights on or off during sex?
Any that are a turn off?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
92~ Have you ever had or have an STD? How many? What was it?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
29- How superstitious are you?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you like the “69” position? Do you prefer to be on top or bottom?
5- Have you ever been hypnotized? Would you allow yourself to be?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Will you cheat again? How can, you be sure? Define what cheating is to you.
How well do you know me? And some of your thoughts about me
71~ Would you give your partner a hand or foot job? Would you receive one?
Nothing too Serious
What was the longest? What was the shortest?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
26~ What side of the bed do you sleep on?
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?
*** Questions about Relationships/Past ***
8- What are your thoughts on politics?
27- What was/ is nickname? Does it have a meaning behind it?
31- If given a chance to be immortal, would you take it? Why?
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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
Any that are a turn off?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
10- List 5 of your top pet peeves.
Nurse/Patient Celebrity/Fan
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
15- What bad habit do you wish you could quit? Do you have any addictions?
8- What's your favorite flavor of ice cream? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you do it again, and would you rather 2 females or 2 males?
1- What’s your favorite animal? Do you a least favorite?
*** Questions About Me ***
5~ When you first started having sex, was it what you thought it would be?
You know that I will be 100% truthful, so ask.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
65~ Describe the best orgasm you’ve ever had? Care to share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
*** Deal Breaker Questions ***
12- What is the weirdest thing you've ever eaten?
47~ What would be your dream job and why?
61~ How willing would you be to try new sexual positions?
Have you ever? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
92~ Everyone needs a “safe” word. What is yours?
How old are you? Male or Female?
I would allow you to do it… What would you do to me?
84~ How do you feel about reading/listening to adult stories?
3- What’s your favorite smell? Do you a least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
If you say it, I will stop, and we can talk about it when you are ready.
The Ice Breaker Questions
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
12- What’s your favorite food? What’s your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you like it when they show and tell you what they want?
13~ Is there a difference between, making love, having sex, and fucking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
What have you learned about yourself that you did not before this?
19~ Who/when was your first “heartbreak”?
Would you allow me to clean every part of your body with my soapy hands and fingers?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Master/Slave Boss/Maid
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
*** Random Questions ***
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
What is your favorite position? Why?
How many partners have you had oral sex with? Who? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
28- What are some things that people do that irritate you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Will you kiss after your partner has gone down on you? Swallow or spit semen?
22- What is your favorite childhood memory? What is your least favorite?
18~ Who/when was your first “crush”?
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?
83~ How do you feel about Porn?
50~ How many children do you have? What are their ages?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
*** What’s Your Favorite…? ***
34- Ever been to a concert? What was your favorite? Who would you like to see?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Do you have a favorite? Is it ok if your partner does?
* Give a rating for each one (0-100)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What do you dislike about me? I asked you to be 100% honest.
What would you say to prove to yourself that it was really you?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
76~ Have you had a threesome? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Does the thought excite you? Care to share?
39~ What are your love languages?
1~ How old were you when you had your first kiss? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
Would you ever want to be woken up with oral and/or intercourse?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
14- What's your favorite dessert? Do you a least 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.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
21- What's your favorite way to spend a weekend or time off?
49~ How many times have you been married? Why did they end?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Do you watch it? What is your favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
22- Do you have any birth marks? How about scars? Care to share how you got them?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
37- Do you like your name? If you could change it, what would you change it too?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
62~ Have you used adult toys?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Model/Photographer Police/Criminal
42~ What’s your biggest regret in life?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
2- What’s your favorite color? Do you a least favorite?
How about if they talk dirty and/or call you names?
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)
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What have you learned about me that was new and/or surprising?
Would you mind if your partner watched it? How about together vs alone?
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?
21~ What was the best date you ever went on? What has been the worst?
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…
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,
3- What Superhero or Superpower would you want to be/have?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
40~ What’s the weirdest place you’ve ever had sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
1- What was your first impression of me? Has it changed?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
30~ What's something unexpected that turns you on?
What is your view on sex? Meaning, When/Where/ How often/
Teacher/Student Stranger/One Night Stand
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
17- Have you ever done drugs? Which ones? How often?
Can you Deep Throat? Do you like the taste of yourself?
10~ How many dates are necessary before you to have sex with someone?
51~ What tends to bring a smile to your face?
67~ Do you like it when your partner moans and/or is vocal during sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
38~ Share your most embarrassing sexual memory?
If you win, what will you make them do?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Get this wrong and this could mean the end… :-) some funny, some not…
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
48~ Have you ever paid or been paid for sex?