What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 05:10
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
10~ How many dates are necessary before you to have sex with someone?
13- How about having a certain hair cut/style?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
This Week In Space podcast: Episode 165 — Guardians of Space - Space
Do you watch it? What is your favorite?
18- How often do you drink alcohol? What is your favorite drink?
51~ Are you willing to play adult games with your partner?
How do the youth in Taiwan perceive their national identity in relation to China?
3- Should Pluto still be considered a planet? 4- How about smoking?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- What Superhero or Superpower would you want to be/have?
14- What's your favorite dessert? Do you a least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Was Jimmy Carter a good President of the United States?
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 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
50~ How many children do you have? What are their ages?
Why do some guys treat girls so badly?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
61~ How willing would you be to try new sexual positions?
84~ How do you feel about reading/listening to adult stories?
Dakota Johnson Raves About Working With First Intimacy Coordinator: “It’s Not Sexy” - Deadline
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
29- How superstitious are you?
Would you do it again, and would you rather 2 females or 2 males?
Why did the American's mulberry harbor not hold up after D-Day?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What have you learned about me that was new and/or surprising?
How many times do you think you have “made love”?
Can a Trump supporter explain what was wrong with what Bishop Budde said to Donald Trump?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
18~ Who/when was your first “crush”?
Doctor/Nurse Stripper/Client
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
*** Questions about Relationships/Past ***
Why do I feel like something bad is going to happen to me?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
22- What is your favorite childhood memory? What is your least favorite?
What is the difference between heaven and heavens?
12- What is the weirdest thing you've ever eaten?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
4- For a pet, Cat, dog or other?
What is your most erotic sex story?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How do you take your erotic photos and how do you choose the poses?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13~ Is there a difference between, making love, having sex, and fucking?
10- What is your favorite family tradition? What’s your least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
11- List at least 5 things on your bucket list. Have you done any of them already?
*** Questions About Me ***
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
22- Do you have any birth marks? How about scars? Care to share how you got them?
15- What bad habit do you wish you could quit? Do you have any addictions?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What was the longest? What was the shortest?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
What is your favorite toy? Ever wanted to try a specific toy?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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,
1- What’s your favorite animal? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
13- What’s your favorite drink? What’s your least favorite?
83~ How do you feel about Porn?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
38~ Share your most embarrassing sexual memory?
19~ Who/when was your first “heartbreak”?
7-What do I do in bed that drives you wild? How about, what turns you off?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
21~ What was the best date you ever went on? What has been the worst?
Escort/Client Job Applicant/Hiring Manager
5~ When you first started having sex, was it what you thought it would be?
1- What was your first impression of me? Has it changed?
What would you say to prove to yourself that it was really you?
Do you think this brought you closer together?
52~ What are your hobbies?
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?
71~ Would you give your partner a hand or foot job? Would you receive one?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Prisoner/Prison Guard Landlord/Tenant
46~ Have you ever used furniture, or other types of things to aid you while having sex?
*** Deal Breaker Questions ***
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
89~ Do you like taking showers together?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Please share Did you stop?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
60~ How important is oral sex? Do you like receiving? Do you like giving?
92~ Everyone needs a “safe” word. What is yours?
*** What’s Your Favorite…? ***
28- What are some things that people do that irritate you?
I would allow you to do it… What would you do to me?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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 yes, what?
Would you ever want to be woken up with oral and/or intercourse?
The Ice Breaker Questions
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
70~ Would/do you have/like anal sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
23- What is your dream job? What was it as a child?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
What do you dislike about me? I asked you to be 100% honest.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
* Give a rating for each one (0-100)
If you win, what will you make them do?
29~ What are some things that turn you off? What is your biggest turn off?
62~ Have you used adult toys?
Do you like the “69” position? Do you prefer to be on top or bottom?
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- List 5 of your top pet peeves.
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?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
40~ What’s the weirdest place you’ve ever had sex?
52~ Are you willing to make “those types” of bets with your partner?
31- If given a chance to be immortal, would you take it? Why?
Nurse/Patient Celebrity/Fan
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Can you Deep Throat? Do you like the taste of yourself?
19- Do/have you smoked? What do you prefer? How often?
17- What’s your favorite holiday? What’s your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
37- Do you like your name? If you could change it, what would you change it too?
Do you have a favorite? Is it ok if your partner does?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
33- If you could visit any time period, when would you pick? Please explain why?
9~ How many times over your lifetime do you think you have had sex so far?
47~ What would be your dream job and why?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
7- What are your thoughts on religion? Is there an afterlife?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
2- What’s your favorite color? Do you a least favorite?
*** Random Questions ***
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Model/Photographer Police/Criminal
65~ Describe the best orgasm you’ve ever had? 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)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Nothing too Serious
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you read them together?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Get this wrong and this could mean the end… :-) some funny, some not…
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
How old are you? Male or Female?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you allow me to clean every part of your body with my soapy hands and fingers?
44~ Care to share something about yourself that no one else knows about you?
9- If you could have three wishes, what would they be? Why?
7- What if a person smells a certain way? 8- How about smoking?
20- What’s your favorite candy? What’s your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
13- What is the craziest/scariest thing you've ever done?
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?
36~ What is your favorite time of day to have sex/make love?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
92~ Have you ever had or have an STD? How many? What was it?
Would /have you ever given your partner a lap dance and Striptease?
53~ How much can you tell me about the one thing you are most passionate about?
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…
1~ How old were you when you had your first kiss? Who? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
25~ How do you feel about PDA? (Public Display of Affection)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
9- What’s your favorite season and why? What’s your least favorite?
32- What's your greatest talent? Can I see it right now?
81~ Do you have any kinks and/or fetishes?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
21- What's your favorite way to spend a weekend or time off?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
19- What’s your favorite fairytale? What’s your least favorite?
Master/Slave Boss/Maid
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Does the thought excite you? Care to share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
34~ Do you like the lights on or off during sex?
64~ When was your very first orgasm? When was your first from having sex? 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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
42~ What’s your biggest regret in life?
Family Relation Age Play
How many partners have you had oral sex with? Who? Care to Share?
49~ How many times have you been married? Why did they end?
What is your view on sex? Meaning, When/Where/ How often/
9- Is there something you’ve always wanted to ask me but you’re afraid?
33- Beach or Mountains? Or is there another place to like better?
11~ Have you ever been caught by your parents or children or others while having sex?
What is your favorite position? Why?
12- What’s your favorite food? What’s your least favorite?
Have you ever? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
48~ Do you have any siblings? Are you close to your family?
How about if they talk dirty and/or call you names?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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)
If you say it, I will stop, and we can talk about it when you are ready.
17- Have you ever done drugs? Which ones? How often?
48~ Have you ever paid or been paid for sex?
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?
Any that are a turn off?
Would you mind if your partner watched it? How about together vs alone?
30~ What's something unexpected that turns you on?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
(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…)
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)
39~ What are your love languages?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
76~ Have you had a threesome? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
Over time has your thoughts on sex changed?
Do you like it when they show and tell you what they want?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
You know that I will be 100% truthful, so ask.
67~ Do you like it when your partner moans and/or is vocal during sex?
26~ What side of the bed do you sleep on?
Any that are a turn off?
How well do you know me? And some of your thoughts about me
8- What are your thoughts on politics?
11- What's your favorite restaurant? What’s your least favorite?
51~ What tends to bring a smile to your face?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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…
3- What’s your favorite smell? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What have you learned about yourself that you did not before this?