What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 14:41
How old are you? Male or Female?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
1~ How old were you when you had your first kiss? Who? Care to Share?
What makes females believe or think abortions are part of a woman’s rights?
11~ Have you ever been caught by your parents or children or others while having sex?
47~ What would be your dream job and why?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
52~ What are your hobbies?
70~ Would/do you have/like anal sex?
13- What is the craziest/scariest thing you've ever done?
UK civil servants who used AI saved two weeks a year, government study finds - Financial Times
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
Do all you people that took the "jab" feel lied to yet?
39~ What are your love languages?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
After trying to buy Ilya Sutskever’s $32B AI startup, Meta looks to hire its CEO - TechCrunch
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?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
7-What do I do in bed that drives you wild? How about, what turns you off?
How can I remove decimals in math?
30~ What's something unexpected that turns you on?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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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?
76~ Have you had a threesome? Care to Share?
Rafael Devers Made Worst Announcement For Red Sox Fans - Sports Illustrated
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
22- What is your favorite childhood memory? What is your least favorite?
How many times do you think you have “made love”?
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22- Do you have any birth marks? How about scars? Care to share how you got them?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
Why do you think Filipinos are conservatives?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you do it again, and would you rather 2 females or 2 males?
Microsoft Retires Legendary 'Blue Screen of Death' After 40 Years of Frowny Faces - CNET
If yes, what?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
34~ Do you like the lights on or off during sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
48~ Have you ever paid or been paid for sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
15- What's your favorite saying? What word or phrase is your least favorite?
Nothing too Serious
What was the longest? What was the shortest?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
9~ How many times over your lifetime do you think you have had sex so far?
Do you like it when they show and tell you what they want?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What is your view on sex? Meaning, When/Where/ How often/
What is your favorite toy? Ever wanted to try a specific toy?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Doctor/Nurse Stripper/Client
42~ What’s your biggest regret in life?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
19~ Who/when was your first “heartbreak”?
(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…)
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
*** Deal Breaker Questions ***
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
28~ What are some things that turn on? What is your biggest turn on?
10- List 5 of your top pet peeves.
Will you cheat again? How can, you be sure? Define what cheating is to you.
Have you ever? Care to Share?
89~ Do you like taking showers together?
7- What if a person smells a certain way? 8- How about smoking?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
13- What’s your favorite drink? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
14- What's your favorite dessert? 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.?
If you win, what will you make them do?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
25~ How do you feel about PDA? (Public Display of Affection)
Nurse/Patient Celebrity/Fan
How about if they talk dirty and/or call you names?
1- What was your first impression of me? Has it changed?
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)
*** Random Questions ***
What is your favorite position? Why?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
6- Do you have dreams? Can you remember them? What do you usually dream about?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
20- What’s your favorite candy? What’s your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
Escort/Client Job Applicant/Hiring Manager
83~ How do you feel about Porn?
18~ Who/when was your first “crush”?
Master/Slave Boss/Maid
Please share Did you stop?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
23- What is your dream job? What was it as a child?
Over time has your thoughts on sex changed?
9- What’s your favorite season and why? What’s your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Do you watch it? What is your favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
29~ What are some things that turn you off? What is your biggest turn off?
Can you Deep Throat? Do you like the taste of yourself?
31- If given a chance to be immortal, would you take it? Why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
81~ Do you have any kinks and/or fetishes?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
65~ Describe the best orgasm you’ve ever had? Care to share?
12- What’s your favorite food? What’s your least favorite?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Would you allow me to clean every part of your body with my soapy hands and fingers?
Would you read them together?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Repairman/Lonely Wife Virgin/Experienced
28- What are some things that people do that irritate you?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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…
51~ Are you willing to play adult games with your partner?
15~ Have you ever been “in love”? Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How well do you know me? And some of your thoughts about me
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
13- How about having a certain hair cut/style?
What have you learned about yourself that you did not before this?
4- For a pet, Cat, dog or other?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Get this wrong and this could mean the end… :-) some funny, some not…
Any that are a turn off?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
50~ How many children do you have? What are their ages?
8- What's your favorite flavor of ice cream? Do you a least favorite?
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,
8- What are your thoughts on politics?
10- What is your favorite family tradition? 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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
32- What's your greatest talent? Can I see it right now?
36- Do you play video games? What is your favorite? Do you a 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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
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?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
*** What’s Your Favorite…? ***
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Prisoner/Prison Guard Landlord/Tenant
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
The Ice Breaker Questions
26~ What side of the bed do you sleep on?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
92~ Have you ever had or have an STD? How many? What was it?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Any that are a turn off?
How many partners have you had oral sex with? Who? Care to Share?
21- What's your favorite way to spend a weekend or time off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7- What are your thoughts on religion? Is there an afterlife?
I would allow you to do it… What would you do to me?
If you say it, I will stop, and we can talk about it when you are ready.
9- If you could have three wishes, what would they be? Why?
3- What Superhero or Superpower would you want to be/have?
15- What bad habit do you wish you could quit? Do you have any addictions?
19- Do/have you smoked? What do you prefer? How often?
49~ How many times have you been married? Why did they end?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
2- What’s your favorite color? Do you a 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?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
52~ Are you willing to make “those types” of bets with your partner?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
11- List at least 5 things on your bucket list. Have you done any of them already?
37- Do you like your name? If you could change it, what would you change it too?
45~ How do you feel about me blindfolding you? How about blindfolding me?
*** Questions About Me ***
92~ Everyone needs a “safe” word. What is yours?
84~ How do you feel about reading/listening to adult stories?
*** Questions about Relationships/Past ***
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
67~ Do you like it when your partner moans and/or is vocal during sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Do you think this brought you closer together?
62~ Have you used adult toys?
38~ Share your most embarrassing sexual memory?
19- What’s your favorite fairytale? What’s your least favorite?
33- If you could visit any time period, when would you pick? Please explain 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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you mind if your partner watched it? How about together vs alone?
* Give a rating for each one (0-100)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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…
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
14- What is an embarrassing moment in your life? How about your most embarrassing?
12- What is the weirdest thing you've ever eaten?
61~ How willing would you be to try new sexual positions?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
What would you say to prove to yourself that it was really you?
36~ What is your favorite time of day to have sex/make love?
53~ How much can you tell me about the one thing you are most passionate about?
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?
17- Have you ever done drugs? Which ones? How often?
Model/Photographer Police/Criminal
44~ Care to share something about yourself that no one else knows about you?
51~ What tends to bring a smile to your face?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you like the “69” position? Do you prefer to be on top or bottom?
That one or two things that made you go hmmmm, OMG or wow!
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?
10~ How many dates are necessary before you to have sex with someone?
Teacher/Student Stranger/One Night Stand
34- Ever been to a concert? What was your favorite? Who would you like to see?
What do you dislike about me? I asked you to be 100% honest.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
48~ Do you have any siblings? Are you close to your family?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
29- How superstitious are you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
3- What’s your favorite smell? Do you a least favorite?
You know that I will be 100% truthful, so ask.
80~ Share your top three fantasies/desires. (Be detailed) 😊
5- Have you ever been hypnotized? Would you allow yourself to be?
82~ Do you have any fantasies involving Role-Playing?
If NO, would you ever have one? Would it be with 2 men or 2 women?
71~ Would you give your partner a hand or foot job? Would you receive one?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
3- Should Pluto still be considered a planet? 4- How about smoking?
Family Relation Age Play
18- How often do you drink alcohol? What is your favorite drink?
11- How about if they like a certain sports team? 12-How about drinking too much?
1- What’s your favorite animal? Do you a least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
33- Beach or Mountains? Or is there another place to like better?
11- What's your favorite restaurant? What’s your least favorite?
Does the thought excite you? Care to share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Would you ever want to be woken up with oral and/or intercourse?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?