What is the most interesting question you can ask to get to know someone?
Last Updated: 29.06.2025 06:42
9- If you could have three wishes, what would they be? Why?
21~ What was the best date you ever went on? What has been the worst?
Doctor/Nurse Stripper/Client
Which branch of engineering is better: ECE or Civil?
11- What's your favorite restaurant? What’s your least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
18~ Who/when was your first “crush”?
Two former Polygon writers are starting a new site - The Verge
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What would you say to prove to yourself that it was really you?
Would you do it again, and would you rather 2 females or 2 males?
Tomato Recall Escalates to Highest Health Risk Alert—Here’s What You Need to Know - Real Simple
Over time has your thoughts on sex changed?
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?
What is your favorite position? Why?
Liam Coen: I think Trevor Lawrence’s footwork has drastically improved - NBC Sports
22- Do you have any birth marks? How about scars? Care to share how you got them?
21- What's your favorite way to spend a weekend or time off?
Would you mind if your partner watched it? How about together vs alone?
Do you like it when they show and tell you what they want?
19- What’s your favorite fairytale? What’s your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Buffalo Trace Adds Eagle Rare 12 To Its Permanent Lineup Of Age-Stated Bourbons - Forbes
51~ What tends to bring a smile to your face?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
2- What’s your favorite color? Do you a least favorite?
Apple issues urgent warning to all 1.8 billion iPhone users - ladbible.com
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
4- For a pet, Cat, dog or other?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
52~ What are your hobbies?
How many times do you think you have “made love”?
How do you feel about Trump saying Ukraine 'should have never started war with Russia'?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
80~ Share your top three fantasies/desires. (Be detailed) 😊
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
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?
Greetings from Warsaw, Poland, where the flags are flying ahead of a key election - NPR
10- List 5 of your top pet peeves.
10- What is your favorite family tradition? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
Why do Democrats look like snowflakes and Republicans look like Vikings?
83~ How do you feel about Porn?
1- What was your first impression of me? Has it changed?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What are the downsides of OpenAI's chain-of-thought approach in the o1 model?
44~ Care to share something about yourself that no one else knows about you?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
11- List at least 5 things on your bucket list. Have you done any of them already?
Does the thought excite you? Care to share?
Eligendi molestiae corrupti numquam voluptatum doloremque laudantium eum.
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
1- What’s your favorite animal? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
28~ What are some things that turn on? What is your biggest turn on?
51~ Are you willing to play adult games with your partner?
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?
31- If given a chance to be immortal, would you take it? Why?
That one or two things that made you go hmmmm, OMG or wow!
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Nothing too Serious
How old are you? Male or Female?
What was the longest? What was the shortest?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How many partners have you had oral sex with? Who? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Prisoner/Prison Guard Landlord/Tenant
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
If you win, what will you make them do?
Escort/Client Job Applicant/Hiring Manager
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?
9- What’s your favorite season and why? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
15- What bad habit do you wish you could quit? Do you have any addictions?
15~ Have you ever been “in love”? Who? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
92~ Everyone needs a “safe” word. What is yours?
32- What's your greatest talent? Can I see it right now?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
42~ What’s your biggest regret in life?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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…
Would /have you ever given your partner a lap dance and Striptease?
82~ Do you have any fantasies involving Role-Playing?
3- What Superhero or Superpower would you want to be/have?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
29~ What are some things that turn you off? What is your biggest turn off?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Get this wrong and this could mean the end… :-) some funny, some not…
9~ How many times over your lifetime do you think you have had sex so far?
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)
37- Do you like your name? If you could change it, what would you change it too?
3- What’s your favorite smell? Do you a least favorite?
50~ How many children do you have? What are their ages?
I would allow you to do it… What would you do to me?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
34~ Do you like the lights on or off during sex?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What have you learned about me that was new and/or surprising?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
*** Deal Breaker Questions ***
33- If you could visit any time period, when would you pick? Please explain why?
Family Relation Age Play
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Any that are a turn off?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
89~ Do you like taking showers together?
Would you allow me to clean every part of your body with my soapy hands and fingers?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
67~ Do you like it when your partner moans and/or is vocal during sex?
81~ Do you have any kinks and/or fetishes?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
12- What’s your favorite food? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Do you watch it? What is your favorite?
84~ How do you feel about reading/listening to adult stories?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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~ Are there moments in your past that you would want to change? Please share 3 of them.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
You know that I will be 100% truthful, so ask.
*** Random Questions ***
19~ Who/when was your first “heartbreak”?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Have you ever? Care to Share?
29- How superstitious are you?
92~ Have you ever had or have an STD? How many? What was it?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
52~ Are you willing to make “those types” of bets with your partner?
38~ Share your most embarrassing sexual memory?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
19- Do/have you smoked? What do you prefer? How often?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
12- What is the weirdest thing you've ever eaten?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
40~ What’s the weirdest place you’ve ever had sex?
Teacher/Student Stranger/One Night Stand
23- What is your dream job? What was it as a child?
36- Do you play video games? What is your favorite? Do you a least favorite?
The Ice Breaker Questions
62~ Have you used adult toys?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Would you ever want to be woken up with oral and/or intercourse?
(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…)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
49~ How many times have you been married? Why did they end?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
1~ How old were you when you had your first kiss? Who? Care to Share?
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
14- What's your favorite dessert? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
30~ What's something unexpected that turns you on?
What is your view on sex? Meaning, When/Where/ How often/
11~ Have you ever been caught by your parents or children or others while having sex?
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How well do you know me? And some of your thoughts about me
Do you have a favorite? Is it ok if your partner does?
13- What’s your favorite drink? What’s your least favorite?
If yes, what?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
7- What if a person smells a certain way? 8- How about smoking?
33- Beach or Mountains? Or is there another place to like better?
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?
17- Have you ever done drugs? Which ones? How often?
5~ When you first started having sex, was it what you thought it would be?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
9- Is there something you’ve always wanted to ask me but you’re afraid?
76~ Have you had a threesome? Care to Share?
* Give a rating for each one (0-100)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
26~ What side of the bed do you sleep on?
7- What are your thoughts on religion? Is there an afterlife?
Can you Deep Throat? Do you like the taste of yourself?
Master/Slave Boss/Maid
8- What's your favorite flavor of ice cream? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Please share Did you stop?
What have you learned about yourself that you did not before this?
15- What's your favorite saying? What word or phrase is your least favorite?
70~ Would/do you have/like anal sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
22- What is your favorite childhood memory? What is your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
48~ Have you ever paid or been paid for sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What do you dislike about me? I asked you to be 100% honest.
Would you read them together?
What is your favorite toy? Ever wanted to try a specific toy?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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,
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
65~ Describe the best orgasm you’ve ever had? 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.
49~ If you could, would you want to be the opposite sex for a day, week, or year?
13~ Is there a difference between, making love, having sex, and fucking?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
8- What are your thoughts on politics?
13- How about having a certain hair cut/style?
39~ What are your love languages?
60~ How important is oral sex? Do you like receiving? Do you like giving?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
47~ What would be your dream job and why?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
13- What is the craziest/scariest thing you've ever done?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
*** Questions About Me ***
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
How about if they talk dirty and/or call you names?
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?
48~ Do you have any siblings? Are you close to your family?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Nurse/Patient Celebrity/Fan
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If NO, would you ever have one? Would it be with 2 men or 2 women?
*** Questions about Relationships/Past ***
14- What is an embarrassing moment in your life? How about your most embarrassing?
5- Have you ever been hypnotized? Would you allow yourself to be?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Any that are a turn off?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
10~ How many dates are necessary before you to have sex with someone?
61~ How willing would you be to try new sexual positions?
Model/Photographer Police/Criminal
*** What’s Your Favorite…? ***
53~ How much can you tell me about the one thing you are most passionate about?
28- What are some things that people do that irritate you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you think this brought you closer together?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
34- Ever been to a concert? What was your favorite? Who would you like to see?
71~ Would you give your partner a hand or foot job? Would you receive one?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7-What do I do in bed that drives you wild? How about, what turns you off?