What is the most interesting question you can ask to get to know someone?
Last Updated: 24.06.2025 05:28
Doctor/Nurse Stripper/Client
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Nothing too Serious
23andMe Sets New Auction With $305 Million New Bid From Ex-CEO - Bloomberg
11- List at least 5 things on your bucket list. Have you done any of them already?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
One year from World Cup opener, FIFA leaves questions unanswered on tickets and security - AP News
61~ How willing would you be to try new sexual positions?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
19~ Who/when was your first “heartbreak”?
Legion of 50 strong as Seahawks reveal Top 50 players in franchise history - Field Gulls
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
*** What’s Your Favorite…? ***
NFL Declines Comment on Viral Video of Patriots' Stefon Diggs Partying on Boat - Bleacher Report
19- Do/have you smoked? What do you prefer? How often?
Do you watch it? What is your favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
How do you feel about Trump saying Ukraine 'should have never started war with Russia'?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
9- Is there something you’ve always wanted to ask me but you’re afraid?
51~ Are you willing to play adult games with your partner?
Why can’t conservatives accept the fact that they are stupid?
(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…)
Does the thought excite you? Care to share?
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…
Is it true that in 2028 there will be a new AIDS variant that will wipe out all the LBGTQ+ people?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
17- What’s your favorite holiday? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How do flat Earthers explain the existence of other spherical planets?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If you win, what will you make them do?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Scoop: Treasury officials defend "revenge tax" from wary GOP senators - Axios
81~ Do you have any kinks and/or fetishes?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
What is your favorite position? Why?
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If NO, would you ever have one? Would it be with 2 men or 2 women?
10- List 5 of your top pet peeves.
34- Ever been to a concert? What was your favorite? Who would you like to see?
7 storylines to watch with All-Star voting underway - MLB.com
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.
*** Questions About Me ***
What is the impact of being stereotyped as poor on an individual's life? How does it make them feel?
9- What’s your favorite season and why? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Stress-Linked Brain Pathway Disrupts Sleep and Memory - Neuroscience News
7- What if a person smells a certain way? 8- How about smoking?
Get this wrong and this could mean the end… :-) some funny, some not…
1~ How old were you when you had your first kiss? Who? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
15~ Have you ever been “in love”? Who? Care to Share?
Where you live may affect your risk of dementia, UCSF study finds - San Francisco Chronicle
32- What's your greatest talent? Can I see it right now?
That one or two things that made you go hmmmm, OMG or wow!
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
12- What’s your favorite food? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
Have you ever? Care to Share?
21- What's your favorite way to spend a weekend or time off?
11~ Have you ever been caught by your parents or children or others while having sex?
How about if they talk dirty and/or call you names?
84~ How do you feel about reading/listening to adult stories?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
If YES, was it with 2 men or 2 women? Did you enjoy it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
10- What is your favorite family tradition? What’s your least favorite?
33- Beach or Mountains? Or is there another place to like better?
8- What's your favorite flavor of ice cream? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
*** Random Questions ***
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Over time has your thoughts on sex changed?
What have you learned about me that was new and/or surprising?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
8- What are your thoughts on politics?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
21~ What was the best date you ever went on? What has been the worst?
42~ What’s your biggest regret in life?
The Ice Breaker Questions
13- What’s your favorite drink? What’s your least favorite?
Do you like it when they show and tell you what they want?
How well do you know me? And some of your thoughts about me
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Can you Deep Throat? Do you like the taste of yourself?
Do you have a favorite? Is it ok if your partner does?
52~ Are you willing to make “those types” of bets with your partner?
39~ What are your love languages?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
48~ Do you have any siblings? Are you close to your family?
2- What’s your favorite color? Do you a least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
4- For a pet, Cat, dog or other?
Will you cheat again? How can, you be sure? Define what cheating is to you.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Escort/Client Job Applicant/Hiring Manager
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Please share Did you stop?
50~ How many children do you have? What are their ages?
10~ How many dates are necessary before you to have sex with someone?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How old are you? Male or Female?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
31- If given a chance to be immortal, would you take it? Why?
92~ Everyone needs a “safe” word. What is yours?
14- What's your favorite dessert? Do you a least favorite?
I would allow you to do it… What would you do to me?
1- What was your first impression of me? Has it changed?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
25~ How do you feel about PDA? (Public Display of Affection)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Do you think this brought you closer together?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Family Relation Age Play
7-What do I do in bed that drives you wild? How about, what turns you off?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What is your view on sex? Meaning, When/Where/ How often/
3- What was the most surprising thing you’ve learned about me throughout our relationship?
5- Have you ever been hypnotized? Would you allow yourself to be?
17- Have you ever done drugs? Which ones? How often?
18- How often do you drink alcohol? What is your favorite drink?
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…
65~ Describe the best orgasm you’ve ever had? Care to share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
22- Do you have any birth marks? How about scars? Care to share how you got them?
83~ How do you feel about Porn?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
What have you learned about yourself that you did not before this?
Teacher/Student Stranger/One Night Stand
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
28~ What are some things that turn on? What is your biggest turn on?
62~ Have you used adult toys?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
13~ Is there a difference between, making love, having sex, and fucking?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
82~ Do you have any fantasies involving Role-Playing?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
23- What is your dream job? What was it as a child?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
29~ What are some things that turn you off? What is your biggest turn off?
47~ What would be your dream job and why?
38~ Share your most embarrassing sexual memory?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
29- How superstitious are you?
36~ What is your favorite time of day to have sex/make love?
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?
*** Questions about Relationships/Past ***
40~ What’s the weirdest place you’ve ever had sex?
Prisoner/Prison Guard Landlord/Tenant
7- What are your thoughts on religion? Is there an afterlife?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
13- How about having a certain hair cut/style?
Any that are a turn off?
52~ What are your hobbies?
14- What is an embarrassing moment in your life? How about your most embarrassing?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
33- If you could visit any time period, when would you pick? Please explain why?
3- What Superhero or Superpower would you want to be/have?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Master/Slave Boss/Maid
Would /have you ever given your partner a lap dance and Striptease?
51~ What tends to bring a smile to your face?
15- What's your favorite saying? What word or phrase is your least favorite?
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?
What do you dislike about me? I asked you to be 100% honest.
44~ Care to share something about yourself that no one else knows about you?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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)
How many partners have you had oral sex with? Who? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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- Do you have dreams? Can you remember them? What do you usually dream about?
Any that are a turn off?
30~ What's something unexpected that turns you on?
Would you mind if your partner watched it? How about together vs alone?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
3- What’s your favorite smell? Do you a least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
20- What’s your favorite candy? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
53~ How much can you tell me about the one thing you are most passionate about?
5~ When you first started having sex, was it what you thought it would be?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you read them together?
26~ What side of the bed do you sleep on?
70~ Would/do you have/like anal sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
48~ Have you ever paid or been paid for sex?
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)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
9~ How many times over your lifetime do you think you have had sex so far?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
92~ Have you ever had or have an STD? How many? What was it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9- If you could have three wishes, what would they be? Why?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Nurse/Patient Celebrity/Fan
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
12- What is the weirdest thing you've ever eaten?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would you allow me to clean every part of your body with my soapy hands and fingers?
27- What was/ is nickname? Does it have a meaning behind it?
34~ Do you like the lights on or off during sex?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What was the longest? What was the shortest?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
* Give a rating for each one (0-100)
11- What's your favorite restaurant? What’s your least favorite?
28- What are some things that people do that irritate you?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Model/Photographer Police/Criminal
22- What is your favorite childhood memory? What is your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
49~ How many times have you been married? Why did they end?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
18~ Who/when was your first “crush”?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Would you ever want to be woken up with oral and/or intercourse?
How many times do you think you have “made love”?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
89~ Do you like taking showers together?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
What would you say to prove to yourself that it was really you?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
If you say it, I will stop, and we can talk about it when you are ready.
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
Repairman/Lonely Wife Virgin/Experienced
60~ How important is oral sex? Do you like receiving? Do you like giving?
76~ Have you had a threesome? Care to Share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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,
41~ Are there moments in your past that you would want to change? Please share 3 of them.
*** Deal Breaker Questions ***
Do you like the “69” position? Do you prefer to be on top or bottom?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
71~ Would you give your partner a hand or foot job? Would you receive one?
1- What’s your favorite animal? Do you a least favorite?
If yes, what?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?