What is the most interesting question you can ask to get to know someone?
14.06.2025 09:12
17- Have you ever done drugs? Which ones? How often?
Would /have you ever given your partner a lap dance and Striptease?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What was the worst decision you ever did?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Get this wrong and this could mean the end… :-) some funny, some not…
*** What’s Your Favorite…? ***
What is the worst thing your sibling has done?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Why do flat Earthers exist? Why can’t I see the Sun at night? Is it because Earth is not flat?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
14- What's your favorite dessert? Do you a least favorite?
If you win, what will you make them do?
Who was the guy that had sex with the AIDS monkey?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
51~ Are you willing to play adult games with your partner?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
That one or two things that made you go hmmmm, OMG or wow!
Why do a lot of autistic people not know how to style their hair?
7-What do I do in bed that drives you wild? How about, what turns you off?
50~ How many children do you have? What are their ages?
71~ Would you give your partner a hand or foot job? Would you receive one?
If gays can get married, why can't I marry my dog or a cheeseburger?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
6- Do you have dreams? Can you remember them? What do you usually dream about?
How many partners have you had oral sex with? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
19~ Who/when was your first “heartbreak”?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Have you been with a stranger yet?
13- What’s your favorite drink? What’s your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
Nurse/Patient Celebrity/Fan
Why do White people love dogs more than humans?
If yes, what?
What is your favorite toy? Ever wanted to try a specific toy?
10~ How many dates are necessary before you to have sex with someone?
What happens when you get sick in a country with universal healthcare? What's the process like?
Would you ever want to be woken up with oral and/or intercourse?
34- Ever been to a concert? What was your favorite? Who would you like to see?
30~ What's something unexpected that turns you on?
Do other British people agree that the UK should reconquer Ireland?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
9~ How many times over your lifetime do you think you have had sex so far?
What have you learned about yourself that you did not before this?
How is it not psychopathic to use someone for sex, even if they agree?
48~ Do you have any siblings? Are you close to your family?
21~ What was the best date you ever went on? What has been the worst?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
67~ Do you like it when your partner moans and/or is vocal during sex?
What have you learned about me that was new and/or surprising?
29~ What are some things that turn you off? What is your biggest turn off?
26~ What side of the bed do you sleep on?
45~ How do you feel about me blindfolding you? How about blindfolding me?
62~ Have you used adult toys?
Repairman/Lonely Wife Virgin/Experienced
How old are you? Male or Female?
81~ Do you have any kinks and/or fetishes?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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,
32- What's your greatest talent? Can I see it right now?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
31- If given a chance to be immortal, would you take it? Why?
10- List 5 of your top pet peeves.
*** Questions about Relationships/Past ***
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
42~ What’s your biggest regret in life?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
1~ How old were you when you had your first kiss? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
17- What’s your favorite holiday? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
3- What’s your favorite smell? Do you a least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
What is your view on sex? Meaning, When/Where/ How often/
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
*** Random Questions ***
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
12- What is the weirdest thing you've ever eaten?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
(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…)
7- What are your thoughts on religion? Is there an afterlife?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Do you like it when they show and tell you what they want?
52~ What are your hobbies?
18- How often do you drink alcohol? What is your favorite drink?
11- What's your favorite restaurant? What’s your 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?
Does the thought excite you? Care to share?
What is your favorite position? Why?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
*** Questions About Me ***
37- Do you like your name? If you could change it, what would you change it too?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
8- What are your thoughts on politics?
11- List at least 5 things on your bucket list. Have you done any of them already?
29- How superstitious are you?
11- How about if they like a certain sports team? 12-How about drinking too much?
13- What is the craziest/scariest thing you've ever done?
3- What Superhero or Superpower would you want to be/have?
15~ Have you ever been “in love”? Who? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
How well do you know me? And some of your thoughts about me
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
You know that I will be 100% truthful, so ask.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
70~ Would/do you have/like anal sex?
11~ Have you ever been caught by your parents or children or others while having sex?
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 people do that irritate you?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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…
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
28~ What are some things that turn on? What is your biggest turn on?
5- Have you ever been hypnotized? Would you allow yourself to be?
27- What was/ is nickname? Does it have a meaning behind it?
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?
Prisoner/Prison Guard Landlord/Tenant
Any that are a turn off?
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?
25~ How do you feel about PDA? (Public Display of Affection)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
12- What’s your favorite food? What’s your least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
If YES, was it with 2 men or 2 women? Did you enjoy it?
23- What is your dream job? What was it as a child?
Nothing too Serious
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Do you have a favorite? Is it ok if your partner does?
How about if they talk dirty and/or call you names?
Would you allow me to clean every part of your body with my soapy hands and fingers?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Family Relation Age Play
Will you cheat again? How can, you be sure? Define what cheating is to you.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
4- For a pet, Cat, dog or other?
What would you say to prove to yourself that it was really you?
What was the longest? What was the shortest?
The Ice Breaker Questions
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
* Give a rating for each one (0-100)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
21- What's your favorite way to spend a weekend or time off?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
61~ How willing would you be to try new sexual positions?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
10- What is your favorite family tradition? What’s your least favorite?
Would you mind if your partner watched it? How about together vs alone?
19- Do/have you smoked? What do you prefer? How often?
I would allow you to do it… What would you do to me?
39~ What are your love languages?
48~ Have you ever paid or been paid for sex?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
20- What’s your favorite candy? What’s your least favorite?
Model/Photographer Police/Criminal
13- How about having a certain hair cut/style?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Teacher/Student Stranger/One Night Stand
Master/Slave Boss/Maid
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
If you say it, I will stop, and we can talk about it when you are ready.
Can you Deep Throat? Do you like the taste of yourself?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
49~ How many times have you been married? Why did they end?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Please share Did you stop?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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…
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?
1- What’s your favorite animal? Do you a least favorite?
92~ Everyone needs a “safe” word. What is yours?
82~ Do you have any fantasies involving Role-Playing?
3- Should Pluto still be considered a planet? 4- How about smoking?
47~ What would be your dream job and why?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
60~ How important is oral sex? Do you like receiving? Do you like giving?
51~ What tends to bring a smile to your face?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
*** Deal Breaker Questions ***
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
2- What’s your favorite color? Do you a least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
22- What is your favorite childhood memory? What is your least favorite?
9- If you could have three wishes, what would they be? Why?
33- Beach or Mountains? Or is there another place to like better?
15- What's your favorite saying? What word or phrase is your least favorite?
Have you ever? Care to Share?
34~ Do you like the lights on or off during sex?
76~ Have you had a threesome? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Any that are a turn off?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
1- What was your first impression of me? Has it changed?
44~ Care to share something about yourself that no one else knows about you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
8- What's your favorite flavor of ice cream? Do you a least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
84~ How do you feel about reading/listening to adult stories?
Over time has your thoughts on sex changed?
89~ Do you like taking showers together?
83~ How do you feel about Porn?
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)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What do you dislike about me? I asked you to be 100% honest.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
5~ When you first started having sex, was it what you thought it would be?
33- If you could visit any time period, when would you pick? Please explain why?
Doctor/Nurse Stripper/Client
9- What’s your favorite season and why? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
52~ Are you willing to make “those types” of bets with your partner?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Do you think this brought you closer together?
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?
How many times do you think you have “made love”?
Would you read them together?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Do you watch it? What is your favorite?
Escort/Client Job Applicant/Hiring Manager
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
18~ Who/when was your first “crush”?
38~ Share your most embarrassing sexual memory?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?