What is the most interesting question you can ask to get to know someone?
12.06.2025 10:32
9~ How many times over your lifetime do you think you have had sex so far?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
*** What’s Your Favorite…? ***
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
29- How superstitious are you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
(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…)
US-China trade war sideswipes Europe’s carmakers - politico.eu
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?
What would you say to prove to yourself that it was really you?
84~ How do you feel about reading/listening to adult stories?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What will the legacy of Jimmy Carter be in light of his death today at 100?
How old are you? Male or Female?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
15- What's your favorite saying? What word or phrase is your least favorite?
What could a Google ‘Pixel Flip’ do better than the Motorola Razr? - 9to5Google
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
If you say it, I will stop, and we can talk about it when you are ready.
Courtroom chaos erupts as Diddy supporter disrupts trial - WJAC
13- What’s your favorite drink? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
28~ What are some things that turn on? What is your biggest turn on?
Cannabis use in any form directly linked to significant risk of heart damage - Earth.com
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)
What was the longest? What was the shortest?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
17- What’s your favorite holiday? What’s your least favorite?
Are you worried that the 2024 US presidential election will result in a close race?
25~ How do you feel about PDA? (Public Display of Affection)
28- What are some things that people do that irritate you?
8- What's your favorite flavor of ice cream? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
52~ Are you willing to make “those types” of bets with your partner?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What is the general opinion of psychologists on Donald Trump's presidency?
12- What is the weirdest thing you've ever eaten?
20- What’s your favorite candy? What’s your least favorite?
26~ What side of the bed do you sleep on?
47~ What would be your dream job and why?
39~ What are your love languages?
13~ Is there a difference between, making love, having sex, and fucking?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
62~ Have you used adult toys?
Family Relation Age Play
3- What Superhero or Superpower would you want to be/have?
48~ Have you ever paid or been paid for sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
51~ What tends to bring a smile to your face?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Do you watch it? What is your favorite?
I would allow you to do it… What would you do to me?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
67~ Do you like it when your partner moans and/or is vocal during sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Would you ever want to be woken up with oral and/or intercourse?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Repairman/Lonely Wife Virgin/Experienced
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
52~ What are your hobbies?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Model/Photographer Police/Criminal
5- Have you ever been hypnotized? Would you allow yourself to be?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you read them together?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
92~ Have you ever had or have an STD? How many? What was it?
34- Ever been to a concert? What was your favorite? Who would you like to see?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Do you think this brought you closer together?
38~ Share your most embarrassing sexual memory?
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,
What have you learned about me that was new and/or surprising?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Please share Did you stop?
22- What is your favorite childhood memory? What is your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
27- What was/ is nickname? Does it have a meaning behind it?
Any that are a turn off?
11- How about if they like a certain sports team? 12-How about drinking too much?
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?
Would you mind if your partner watched it? How about together vs alone?
7- What are your thoughts on religion? Is there an afterlife?
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?
50~ How many children do you have? What are their ages?
12- What’s your favorite food? What’s your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
80~ Share your top three fantasies/desires. (Be detailed) 😊
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Nothing too Serious
15~ Have you ever been “in love”? Who? Care to Share?
49~ How many times have you been married? Why did they end?
How many partners have you had oral sex with? Who? Care to Share?
Have you ever? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Will you cheat again? How can, you be sure? Define what cheating is to you.
Do you like the “69” position? Do you prefer to be on top or bottom?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
37- Do you like your name? If you could change it, what would you change it too?
17- Have you ever done drugs? Which ones? How often?
48~ Do you have any siblings? Are you close to your family?
What do you dislike about me? I asked you to be 100% honest.
Escort/Client Job Applicant/Hiring Manager
That one or two things that made you go hmmmm, OMG or wow!
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Doctor/Nurse Stripper/Client
65~ Describe the best orgasm you’ve ever had? Care to share?
19~ Who/when was your first “heartbreak”?
*** Questions about Relationships/Past ***
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?
10- List 5 of your top pet peeves.
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…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Would /have you ever given your partner a lap dance and Striptease?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
Do you have a favorite? Is it ok if your partner does?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
2- What’s your favorite color? Do you a least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
32- What's your greatest talent? Can I see it right now?
Nurse/Patient Celebrity/Fan
13- What is the craziest/scariest thing you've ever done?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
3- What’s your favorite smell? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
3- Should Pluto still be considered a planet? 4- How about smoking?
14- What's your favorite dessert? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
70~ Would/do you have/like anal sex?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
9- What’s your favorite season and why? What’s your least favorite?
83~ How do you feel about Porn?
76~ Have you had a threesome? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What is your favorite position? Why?
11~ Have you ever been caught by your parents or children or others while having sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
*** Questions About Me ***
1- What’s your favorite animal? Do you a least favorite?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
What is your view on sex? Meaning, When/Where/ How often/
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
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?
How well do you know me? And some of your thoughts about me
89~ Do you like taking showers together?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If you win, what will you make them do?
21- What's your favorite way to spend a weekend or time off?
The Ice Breaker Questions
Any that are a turn off?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
* Give a rating for each one (0-100)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would you allow me to clean every part of your body with my soapy hands and fingers?
10~ How many dates are necessary before you to have sex with someone?
36- Do you play video games? What is your favorite? Do you a least favorite?
Over time has your thoughts on sex changed?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
If YES, was it with 2 men or 2 women? Did you enjoy it?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Master/Slave Boss/Maid
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
6- Do you have dreams? Can you remember them? What do you usually dream about?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
45~ How do you feel about me blindfolding you? How about blindfolding me?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
13- How about having a certain hair cut/style?
10- What is your favorite family tradition? What’s your least favorite?
*** Deal Breaker Questions ***
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…
11- List at least 5 things on your bucket list. Have you done any of them already?
*** Random Questions ***
82~ Do you have any fantasies involving Role-Playing?
9- If you could have three wishes, what would they be? Why?
Do you like it when they show and tell you what they want?
11- What's your favorite restaurant? What’s your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
14- What is an embarrassing moment in your life? How about your most embarrassing?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
4- For a pet, Cat, dog or other?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7- What if a person smells a certain way? 8- How about smoking?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
51~ Are you willing to play adult games with your partner?
30~ What's something unexpected that turns you on?
What is your favorite toy? Ever wanted to try a specific toy?
29~ What are some things that turn you off? What is your biggest turn off?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
18~ Who/when was your first “crush”?
5~ When you first started having sex, was it what you thought it would be?
Does the thought excite you? Care to share?
71~ Would you give your partner a hand or foot job? Would you receive one?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Teacher/Student Stranger/One Night Stand
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
44~ Care to share something about yourself that no one else knows about you?
What have you learned about yourself that you did not before this?
34~ Do you like the lights on or off during sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
23- What is your dream job? What was it as a child?
33- Beach or Mountains? Or is there another place to like better?
Can you Deep Throat? Do you like the taste of yourself?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
How about if they talk dirty and/or call you names?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
15- What bad habit do you wish you could quit? Do you have any addictions?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
How many times do you think you have “made love”?
36~ What is your favorite time of day to have sex/make love?
If yes, what?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
53~ How much can you tell me about the one thing you are most passionate about?
21~ What was the best date you ever went on? What has been the worst?
42~ What’s your biggest regret in life?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
31- If given a chance to be immortal, would you take it? Why?
18- How often do you drink alcohol? What is your favorite drink?
8- What are your thoughts on politics?
19- Do/have you smoked? What do you prefer? How often?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
61~ How willing would you be to try new sexual positions?
You know that I will be 100% truthful, so ask.
92~ Everyone needs a “safe” word. What is yours?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
1- What was your first impression of me? Has it changed?