What is the most interesting question you can ask to get to know someone?
13.06.2025 10:47
19- What’s your favorite fairytale? What’s your least favorite?
14- What's your favorite dessert? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
29- How superstitious are you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Hillary thinks we must censor or "we lose total control". Why does she demand total control?
What would you say to prove to yourself that it was really you?
Would you read them together?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Why am I so afraid that gun owners have set traps to kill me outside my house or my car?
Nothing too Serious
Any that are a turn off?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
I'm straight, so why do I love watching guys cum?
71~ Would you give your partner a hand or foot job? Would you receive one?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10- List 5 of your top pet peeves.
What is the difference between anxiety and depressive neurosis?
What have you learned about yourself that you did not before this?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Why is every human messed up in some way?
5- Have you ever been hypnotized? Would you allow yourself to be?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Doctor/Nurse Stripper/Client
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What is a good tool for product analytics besides Google Analytics?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
30~ What's something unexpected that turns you on?
How do Flat Earthers explain time zones?
You know that I will be 100% truthful, so ask.
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
48~ Have you ever paid or been paid for sex?
Please share Did you stop?
6- Do you have dreams? Can you remember them? What do you usually dream about?
If yes, what?
15- What bad habit do you wish you could quit? Do you have any addictions?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
11- How about if they like a certain sports team? 12-How about drinking too much?
32- What's your greatest talent? Can I see it right now?
*** Questions about Relationships/Past ***
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,
83~ How do you feel about Porn?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
42~ What’s your biggest regret in life?
33- Beach or Mountains? Or is there another place to like better?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Family Relation Age Play
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
80~ Share your top three fantasies/desires. (Be detailed) 😊
84~ How do you feel about reading/listening to adult stories?
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…
I would allow you to do it… What would you do to me?
28- What are some things that people do that irritate you?
Would /have you ever given your partner a lap dance and Striptease?
27- What was/ is nickname? Does it have a meaning behind it?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What is your favorite position? Why?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
39~ What are your love languages?
Do you watch it? What is your favorite?
7- What if a person smells a certain way? 8- How about smoking?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
10- What is your favorite family tradition? What’s your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
65~ Describe the best orgasm you’ve ever had? Care to share?
18~ Who/when was your first “crush”?
61~ How willing would you be to try new sexual positions?
29~ What are some things that turn you off? What is your biggest turn off?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What do you dislike about me? I asked you to be 100% honest.
40~ What’s the weirdest place you’ve ever had sex?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Nurse/Patient Celebrity/Fan
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
4- For a pet, Cat, dog or other?
9- If you could have three wishes, what would they be? Why?
13- How about having a certain hair cut/style?
81~ Do you have any kinks and/or fetishes?
Any that are a turn off?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What have you learned about me that was new and/or surprising?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
21- What's your favorite way to spend a weekend or time off?
67~ Do you like it when your partner moans and/or is vocal during sex?
11- List at least 5 things on your bucket list. Have you done any of them already?
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?
62~ Have you used adult toys?
51~ What tends to bring a smile to your face?
3- What Superhero or Superpower would you want to be/have?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
That one or two things that made you go hmmmm, OMG or wow!
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
76~ Have you had a threesome? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you have a favorite? Is it ok if your partner does?
31- If given a chance to be immortal, would you take it? Why?
13~ Is there a difference between, making love, having sex, and fucking?
*** Random Questions ***
89~ Do you like taking showers together?
9~ How many times over your lifetime do you think you have had sex so far?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Would you mind if your partner watched it? How about together vs alone?
44~ Care to share something about yourself that no one else knows about you?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
Prisoner/Prison Guard Landlord/Tenant
7-What do I do in bed that drives you wild? How about, what turns you off?
52~ Are you willing to make “those types” of bets with your partner?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do you like the “69” position? Do you prefer to be on top or bottom?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
17- What’s your favorite holiday? What’s your least favorite?
1- What was your first impression of me? Has it changed?
22- What is your favorite childhood memory? What is your least favorite?
13- What is the craziest/scariest thing you've ever done?
51~ Are you willing to play adult games with your partner?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
If you win, what will you make them do?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
*** Questions About Me ***
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
34~ Do you like the lights on or off during sex?
3- What’s your favorite smell? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would you do it again, and would you rather 2 females or 2 males?
Can you Deep Throat? Do you like the taste of yourself?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
47~ What would be your dream job and 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?
Get this wrong and this could mean the end… :-) some funny, some not…
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?
49~ How many times have you been married? Why did they end?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
15~ Have you ever been “in love”? Who? Care to Share?
8- What are your thoughts on politics?
60~ How important is oral sex? Do you like receiving? Do you like giving?
If YES, was it with 2 men or 2 women? Did you enjoy it?
2- What’s your favorite color? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
12- What is the weirdest thing you've ever eaten?
36~ What is your favorite time of day to have sex/make love?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
22- Do you have any birth marks? How about scars? Care to share how you got them?
Does the thought excite you? Care to share?
9- Is there something you’ve always wanted to ask me but you’re afraid?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
37- Do you like your name? If you could change it, what would you change it too?
19- Do/have you smoked? What do you prefer? How often?
92~ Everyone needs a “safe” word. What is yours?
48~ Do you have any siblings? Are you close to your family?
23- What is your dream job? What was it as a child?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
28~ What are some things that turn on? What is your biggest turn on?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How old are you? Male or Female?
9- What’s your favorite season and why? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you allow me to clean every part of your body with my soapy hands and fingers?
52~ What are your hobbies?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
26~ What side of the bed do you sleep on?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
10~ How many dates are necessary before you to have sex with someone?
11~ Have you ever been caught by your parents or children or others while having sex?
45~ How do you feel about me blindfolding you? How about blindfolding me?
17- Have you ever done drugs? Which ones? How often?
15- What's your favorite saying? What word or phrase is your least favorite?
Master/Slave Boss/Maid
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
21~ What was the best date you ever went on? What has been the worst?
(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…)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
5~ When you first started having sex, was it what you thought it would be?
If NO, would you ever have one? Would it be with 2 men or 2 women?
1- What’s your favorite animal? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
How many partners have you had oral sex with? Who? Care to Share?
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?
Model/Photographer Police/Criminal
What is your view on sex? Meaning, When/Where/ How often/
7- What are your thoughts on religion? Is there an afterlife?
Escort/Client Job Applicant/Hiring Manager
How many times do you think you have “made love”?
How well do you know me? And some of your thoughts about me
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
70~ Would/do you have/like anal sex?
*** Deal Breaker Questions ***
What was the longest? What was the shortest?
* Give a rating for each one (0-100)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Do you think this brought you closer together?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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?
How about if they talk dirty and/or call you names?
19~ Who/when was your first “heartbreak”?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What is your favorite toy? Ever wanted to try a specific toy?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Over time has your thoughts on sex changed?
12- What’s your favorite food? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
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)
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…
Have you ever? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
50~ How many children do you have? What are their ages?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
18- How often do you drink alcohol? What is your favorite drink?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Repairman/Lonely Wife Virgin/Experienced
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?
38~ Share your most embarrassing sexual memory?
25~ How do you feel about PDA? (Public Display of Affection)
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?
The Ice Breaker Questions
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
11- What's your favorite restaurant? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
13- What’s your favorite drink? What’s your least favorite?
*** What’s Your Favorite…? ***