What is the most interesting question you can ask to get to know someone?
08.06.2025 09:42
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Is it possible for the U.S. government to get rid of the constitution for national safety?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
11- How about if they like a certain sports team? 12-How about drinking too much?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
30~ What's something unexpected that turns you on?
11- List at least 5 things on your bucket list. Have you done any of them already?
Would you ever want to be woken up with oral and/or intercourse?
21- What's your favorite way to spend a weekend or time off?
How to watch Apple’s WWDC 2025 keynote - TechCrunch
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Sydney Sweeney and the business of being hot - Yahoo
Do you watch it? What is your favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What did Chandrashekhar Azad say about Hinduism during a podcast?
9~ How many times over your lifetime do you think you have had sex so far?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
18~ Who/when was your first “crush”?
Taking a realistic look at terraforming Mars - Phys.org
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
82~ Do you have any fantasies involving Role-Playing?
29- How superstitious are you?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If you win, what will you make them do?
Can you show pictures of your penis, big or small?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
15~ Have you ever been “in love”? Who? Care to Share?
Master/Slave Boss/Maid
Any that are a turn off?
6- Do you have dreams? Can you remember them? What do you usually dream about?
How do you handle your mother-in-law after you heard her talking badly about you in the next room?
36~ What is your favorite time of day to have sex/make love?
12- What is the weirdest thing you've ever eaten?
3- Should Pluto still be considered a planet? 4- How about smoking?
How could Trump, with his deplorable garbage supporters, manage to win an election?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What is your view on sex? Meaning, When/Where/ How often/
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Why are European countries warning European travelers to be careful traveling to the United States?
Would you read them together?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Teacher/Student Stranger/One Night Stand
27- What was/ is nickname? Does it have a meaning behind it?
13- What’s your favorite drink? What’s your least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Why am I so triggered and depressed over a minor thing?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
60~ How important is oral sex? Do you like receiving? Do you like giving?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Get this wrong and this could mean the end… :-) some funny, some not…
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Nothing too Serious
*** Questions About Me ***
36- Do you play video games? What is your favorite? Do you a least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
19~ Who/when was your first “heartbreak”?
23- What is your dream job? What was it as a child?
Model/Photographer Police/Criminal
81~ Do you have any kinks and/or fetishes?
Would you do it again, and would you rather 2 females or 2 males?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Over time has your thoughts on sex changed?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
52~ Are you willing to make “those types” of bets with your partner?
50~ How many children do you have? What are their ages?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
19- What’s your favorite fairytale? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
51~ Are you willing to play adult games with your partner?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How about if they talk dirty and/or call you names?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
38~ Share your most embarrassing sexual memory?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Nurse/Patient Celebrity/Fan
29~ What are some things that turn you off? What is your biggest turn off?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
If yes, what?
14- What's your favorite dessert? Do you a least favorite?
7- What are your thoughts on religion? Is there an afterlife?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
25~ How do you feel about PDA? (Public Display of Affection)
What is your favorite toy? Ever wanted to try a specific toy?
34~ Do you like the lights on or off during sex?
33- If you could visit any time period, when would you pick? Please explain why?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
*** Deal Breaker Questions ***
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
17- Have you ever done drugs? Which ones? How often?
*** What’s Your Favorite…? ***
Doctor/Nurse Stripper/Client
83~ How do you feel about Porn?
9- What’s your favorite season and why? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Family Relation Age Play
15- What bad habit do you wish you could quit? Do you have any addictions?
22- What is your favorite childhood memory? What is your least favorite?
28~ What are some things that turn on? What is your biggest turn on?
What have you learned about yourself that you did not before this?
1~ How old were you when you had your first kiss? Who? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
1- What’s your favorite animal? 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?
Escort/Client Job Applicant/Hiring Manager
92~ Everyone needs a “safe” word. What is yours?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
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…
Do you shave/trim your pubic hair? For you guys do you shave your balls?
10- List 5 of your top pet peeves.
14- What is an embarrassing moment in your life? How about your most embarrassing?
Can you Deep Throat? Do you like the taste of yourself?
20- What’s your favorite candy? What’s your least favorite?
What would you say to prove to yourself that it was really you?
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,
19- Do/have you smoked? What do you prefer? How often?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Have you ever? Care to Share?
1- What was your first impression of me? Has it changed?
15- What's your favorite saying? What word or phrase is your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
You know that I will be 100% truthful, so ask.
62~ Have you used adult toys?
39~ What are your love languages?
Would you mind if your partner watched it? How about together vs alone?
40~ What’s the weirdest place you’ve ever had sex?
52~ What are your hobbies?
4- For a pet, Cat, dog or other?
*** Questions about Relationships/Past ***
9- If you could have three wishes, what would they be? Why?
What have you learned about me that was new and/or surprising?
Repairman/Lonely Wife Virgin/Experienced
8- What are your thoughts on politics?
53~ How much can you tell me about the one thing you are most passionate about?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
18- How often do you drink alcohol? What is your favorite drink?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
11- What's your favorite restaurant? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
48~ Have you ever paid or been paid for sex?
89~ Do you like taking showers together?
9- Is there something you’ve always wanted to ask me but you’re afraid?
How many times do you think you have “made love”?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
42~ What’s your biggest regret in life?
51~ What tends to bring a smile to your face?
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Prisoner/Prison Guard Landlord/Tenant
What do you dislike about me? I asked you to be 100% honest.
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?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
12- What’s your favorite food? What’s your least favorite?
13- How about having a certain hair cut/style?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Will you cheat again? How can, you be sure? Define what cheating is to you.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
92~ Have you ever had or have an STD? How many? What was it?
10- What is your favorite family tradition? What’s your least favorite?
The Ice Breaker Questions
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
I would allow you to do it… What would you do to me?
65~ Describe the best orgasm you’ve ever had? Care to share?
28- What are some things that people do that irritate you?
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?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
47~ What would be your dream job and why?
Any that are a turn off?
26~ What side of the bed do you sleep on?
61~ How willing would you be to try new sexual positions?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
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?
18- What’s your favorite way to relax after a long day? What’s your 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.
8- What's your favorite flavor of ice cream? Do you a least favorite?
How many partners have you had oral sex with? Who? Care to Share?
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)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
2- What’s your favorite color? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
5- Have you ever been hypnotized? Would you allow yourself to be?
How well do you know me? And some of your thoughts about me
3- What’s your favorite smell? Do you a least favorite?
How old are you? Male or Female?
That one or two things that made you go hmmmm, OMG or wow!
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
76~ Have you had a threesome? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
Do you like the “69” position? Do you prefer to be on top or bottom?
If you say it, I will stop, and we can talk about it when you are ready.
Please share Did you stop?
Do you like it when they show and tell you what they want?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
What was the longest? What was the shortest?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
3- What Superhero or Superpower would you want to be/have?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would /have you ever given your partner a lap dance and Striptease?
84~ How do you feel about reading/listening to adult stories?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
33- Beach or Mountains? Or is there another place to like better?
What is your favorite position? Why?
13- What is the craziest/scariest thing you've ever done?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
49~ How many times have you been married? Why did they end?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
*** Random Questions ***
44~ Care to share something about yourself that no one else knows about you?
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…
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?
Do you think this brought you closer together?
(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…)
21~ What was the best date you ever went on? What has been the worst?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
10~ How many dates are necessary before you to have sex with someone?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Does the thought excite you? Care to share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
5~ When you first started having sex, was it what you thought it would be?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
48~ Do you have any siblings? Are you close to your family?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
37- Do you like your name? If you could change it, what would you change it too?
* Give a rating for each one (0-100)
7-What do I do in bed that drives you wild? How about, what turns you off?
70~ Would/do you have/like anal sex?
71~ Would you give your partner a hand or foot job? Would you receive one?