What is the most interesting question you can ask to get to know someone?
12.06.2025 08:17
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
37- Do you like your name? If you could change it, what would you change it too?
7- What are your thoughts on religion? Is there an afterlife?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
29~ What are some things that turn you off? What is your biggest turn off?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Has anyone ever participated in a gang bang and what was it like?
1- What’s your favorite animal? Do you a least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would you do it again, and would you rather 2 females or 2 males?
Fred Espenak, astronomy's 'Mr. Eclipse', dies at 71 - Space
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
Why am I dreaming of people I've never seen before?
That one or two things that made you go hmmmm, OMG or wow!
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)
Proposed NASA cuts to space science: “Staggering” - EarthSky
15- What bad habit do you wish you could quit? Do you have any addictions?
You know that I will be 100% truthful, so ask.
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Musk threatens to decommission a key space station link for NASA - AP News
Would you ever want to be woken up with oral and/or intercourse?
What would you say to prove to yourself that it was really you?
Over time has your thoughts on sex changed?
49~ How many times have you been married? Why did they end?
Do you like it when they show and tell you what they want?
How about if they talk dirty and/or call you names?
Jordan Ott hiring strengthens questions on Suns’ decision-making tree - Arizona Sports
11~ Have you ever been caught by your parents or children or others while having sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
92~ Have you ever had or have an STD? How many? What was it?
What is a common thought that keeps people up at night? Why do some people experience this?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
10- What is your favorite family tradition? What’s your least favorite?
Sweden’s Maja Stark wins U.S. Women’s Open for first major championship - NBC Sports
18~ Who/when was your first “crush”?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
3- What Superhero or Superpower would you want to be/have?
28~ What are some things that turn on? What is your biggest turn on?
How old are you? Male or Female?
* Give a rating for each one (0-100)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
20- What’s your favorite candy? What’s your least favorite?
Do you watch it? What is your favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Do you have a favorite? Is it ok if your partner does?
38~ Share your most embarrassing sexual memory?
33- If you could visit any time period, when would you pick? Please explain why?
3- What’s your favorite smell? Do you a least favorite?
9- What’s your favorite season and why? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
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?
76~ Have you had a threesome? Care to Share?
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.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
25~ How do you feel about PDA? (Public Display of Affection)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
36- Do you play video games? What is your favorite? Do you a 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.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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 ever given your partner a lap dance and Striptease?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
10~ How many dates are necessary before you to have sex with someone?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Master/Slave Boss/Maid
18- What’s your favorite way to relax after a long day? What’s your least favorite?
29- How superstitious are you?
9- If you could have three wishes, what would they be? Why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
15~ Have you ever been “in love”? Who? Care to Share?
10- List 5 of your top pet peeves.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
84~ How do you feel about reading/listening to adult stories?
23- What is your dream job? What was it as a child?
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 is your view on sex? Meaning, When/Where/ How often/
How many partners have you had oral sex with? Who? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
7- What if a person smells a certain way? 8- How about smoking?
3- Should Pluto still be considered a planet? 4- How about smoking?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
11- How about if they like a certain sports team? 12-How about drinking too much?
83~ How do you feel about Porn?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What is your favorite position? Why?
28- What are some things that people do that irritate you?
13- What’s your favorite drink? What’s your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Escort/Client Job Applicant/Hiring Manager
18- How often do you drink alcohol? What is your favorite drink?
32- What's your greatest talent? Can I see it right now?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
*** Questions about Relationships/Past ***
51~ Are you willing to play adult games with your partner?
Would you allow me to clean every part of your body with my soapy hands and fingers?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
70~ Would/do you have/like anal sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
14- What is an embarrassing moment in your life? How about your most embarrassing?
*** Deal Breaker Questions ***
Do you shave/trim your pubic hair? For you guys do you shave your balls?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
65~ Describe the best orgasm you’ve ever had? Care to share?
How many times do you think you have “made love”?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
26~ What side of the bed do you sleep on?
45~ How do you feel about me blindfolding you? How about blindfolding me?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
Prisoner/Prison Guard Landlord/Tenant
34~ Do you like the lights on or off during sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
30~ What's something unexpected that turns you on?
52~ What are your hobbies?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Doctor/Nurse Stripper/Client
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Can you Deep Throat? Do you like the taste of yourself?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
17- What’s your favorite holiday? What’s your least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Would you read them together?
50~ How many children do you have? What are their ages?
The Ice Breaker Questions
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Please share Did you stop?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
4- For a pet, Cat, dog or other?
42~ What’s your biggest regret in life?
What have you learned about yourself that you did not before this?
Do you think this brought you closer together?
13- How about having a certain hair cut/style?
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…
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
53~ How much can you tell me about the one thing you are most passionate about?
5~ When you first started having sex, was it what you thought it would be?
48~ Do you have any siblings? Are you close to your family?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
27- What was/ is nickname? Does it have a meaning behind it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
12- What’s your favorite food? What’s your least favorite?
If yes, what?
Nurse/Patient Celebrity/Fan
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Does the thought excite you? Care to share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
82~ Do you have any fantasies involving Role-Playing?
62~ Have you used adult toys?
47~ What would be your dream job and why?
11- What's your favorite restaurant? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
48~ Have you ever paid or been paid for sex?
39~ What are your love languages?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
21~ What was the best date you ever went on? What has been the worst?
What have you learned about me that was new and/or surprising?
*** Questions About Me ***
9- Is there something you’ve always wanted to ask me but you’re afraid?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Have you ever? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
15- What's your favorite saying? What word or phrase is your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
33- Beach or Mountains? Or is there another place to like better?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
(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…)
19- What’s your favorite fairytale? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5- Have you ever been hypnotized? Would you allow yourself to be?
Family Relation Age Play
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
17- Have you ever done drugs? Which ones? How often?
19- Do/have you smoked? What do you prefer? How often?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
12- What is the weirdest thing you've ever eaten?
Any that are a turn off?
Nothing too Serious
I would allow you to do it… What would you do to me?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
What do you dislike about me? I asked you to be 100% honest.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
*** What’s Your Favorite…? ***
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
1- What was your first impression of me? Has it changed?
81~ Do you have any kinks and/or fetishes?
Will you cheat again? How can, you be sure? Define what cheating is to you.
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
92~ Everyone needs a “safe” word. What is yours?
*** Random Questions ***
How well do you know me? And some of your thoughts about me
22- What is your favorite childhood memory? What is your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
6- Do you have dreams? Can you remember them? What do you usually dream about?
31- If given a chance to be immortal, would you take it? Why?
13- What is the craziest/scariest thing you've ever done?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What was the longest? What was the shortest?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
14- What's your favorite dessert? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Model/Photographer Police/Criminal
67~ Do you like it when your partner moans and/or is vocal during sex?
89~ Do you like taking showers together?
Do you like the “69” position? Do you prefer to be on top or bottom?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
2- What’s your favorite color? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
22- Do you have any birth marks? How about scars? Care to share how you got them?
If you win, what will you make them do?
Would you mind if your partner watched it? How about together vs alone?
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?
21- What's your favorite way to spend a weekend or time off?
Get this wrong and this could mean the end… :-) some funny, some not…
61~ How willing would you be to try new sexual positions?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
80~ Share your top three fantasies/desires. (Be detailed) 😊
8- What are your thoughts on politics?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
11- List at least 5 things on your bucket list. Have you done any of them already?
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…
19~ Who/when was your first “heartbreak”?
51~ What tends to bring a smile to your face?