What is the most interesting question you can ask to get to know someone?
Last Updated: 22.06.2025 07:46
18- What’s your favorite way to relax after a long day? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
This Expensive-Looking Swivel Chair Will Almost Certainly Sell Out Again - HuffPost
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
*** Questions About Me ***
17- What’s your favorite holiday? What’s your least favorite?
Once-a-week pill for schizophrenia shows promise in clinical trials - MIT News
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
22- Do you have any birth marks? How about scars? Care to share how you got them?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Please share Did you stop?
What would you say to prove to yourself that it was really you?
9- What’s your favorite season and why? What’s your least favorite?
What's the most impressive feature of Claude AI according to its users?
89~ Do you like taking showers together?
71~ Would you give your partner a hand or foot job? Would you receive one?
38~ Share your most embarrassing sexual memory?
Why can't we send flat Earthers to space and show them the shape of Earth?
65~ Describe the best orgasm you’ve ever had? Care to share?
92~ Have you ever had or have an STD? How many? What was it?
5~ When you first started having sex, was it what you thought it would be?
How do you envision the role of AI in software development evolving in the future?
5- Have you ever been hypnotized? Would you allow yourself to be?
You know that I will be 100% truthful, so ask.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
It sounds like WWE has an explosive angle planned for SmackDown - Cageside Seats
44~ Care to share something about yourself that no one else knows about you?
60~ How important is oral sex? Do you like receiving? Do you like giving?
14- What's your favorite dessert? Do you a least favorite?
30~ What's something unexpected that turns you on?
12- What is the weirdest thing you've ever eaten?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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…
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?
19~ Who/when was your first “heartbreak”?
What’s your idea of the perfect Saturday night?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Teacher/Student Stranger/One Night Stand
15~ Have you ever been “in love”? Who? Care to Share?
Analysts revamp forecast for Nvidia-backed AI stock - TheStreet
* Give a rating for each one (0-100)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
48~ Have you ever paid or been paid for sex?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
9- Is there something you’ve always wanted to ask me but you’re afraid?
11~ Have you ever been caught by your parents or children or others while having sex?
18~ Who/when was your first “crush”?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
37- Do you like your name? If you could change it, what would you change it too?
49~ How many times have you been married? Why did they end?
Do you think this brought you closer together?
Get this wrong and this could mean the end… :-) some funny, some not…
47~ What would be your dream job and why?
What have you learned about me that was new and/or surprising?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
33- If you could visit any time period, when would you pick? Please explain why?
53~ How much can you tell me about the one thing you are most passionate about?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
11- What's your favorite restaurant? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
*** What’s Your Favorite…? ***
Over time has your thoughts on sex changed?
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?
25~ How do you feel about PDA? (Public Display of Affection)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What do you dislike about me? I asked you to be 100% honest.
34- Ever been to a concert? What was your favorite? Who would you like to see?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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)
If yes, what?
48~ Do you have any siblings? Are you close to your family?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What is your view on sex? Meaning, When/Where/ How often/
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would you do it again, and would you rather 2 females or 2 males?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
70~ Would/do you have/like anal sex?
9~ How many times over your lifetime do you think you have had sex so far?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
13~ Is there a difference between, making love, having sex, and fucking?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
14- What is an embarrassing moment in your life? How about your most embarrassing?
28~ What are some things that turn on? What is your biggest turn on?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
1~ How old were you when you had your first kiss? Who? Care to Share?
Nothing too Serious
Would you allow me to clean every part of your body with my soapy hands and fingers?
15- What's your favorite saying? What word or phrase is your least favorite?
Any that are a turn off?
11- List at least 5 things on your bucket list. Have you done any of them already?
62~ Have you used adult toys?
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?
51~ Are you willing to play adult games with your partner?
67~ Do you like it when your partner moans and/or is vocal during sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
23- What is your dream job? What was it as a child?
Do you watch it? What is your favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
4- For a pet, Cat, dog or other?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
That one or two things that made you go hmmmm, OMG or wow!
Would you read them together?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
18- How often do you drink alcohol? What is your favorite drink?
13- What is the craziest/scariest thing you've ever done?
Prisoner/Prison Guard Landlord/Tenant
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
50~ How many children do you have? What are their ages?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Do you like it when they show and tell you what they want?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
Do you like the “69” position? Do you prefer to be on top or bottom?
52~ Are you willing to make “those types” of bets with your partner?
*** Random Questions ***
What have you learned about yourself that you did not before this?
10- List 5 of your top pet peeves.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
61~ How willing would you be to try new sexual positions?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Does the thought excite you? Care to share?
29~ What are some things that turn you off? What is your biggest turn off?
I would allow you to do it… What would you do to me?
Will you cheat again? How can, you be sure? Define what cheating is to you.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
8- What's your favorite flavor of ice cream? Do you a least favorite?
2- What’s your favorite color? Do you a least favorite?
13- What’s your favorite drink? What’s your least favorite?
13- How about having a certain hair cut/style?
51~ What tends to bring a smile to your face?
Escort/Client Job Applicant/Hiring Manager
17- Have you ever done drugs? Which ones? How often?
21- What's your favorite way to spend a weekend or time off?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
82~ Do you have any fantasies involving Role-Playing?
What is your favorite toy? Ever wanted to try a specific toy?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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 Superhero or Superpower would you want to be/have?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
32- What's your greatest talent? Can I see it right now?
Nurse/Patient Celebrity/Fan
92~ Everyone needs a “safe” word. What is yours?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
*** Questions about Relationships/Past ***
46~ Have you ever used furniture, or other types of things to aid you while having sex?
81~ Do you have any kinks and/or fetishes?
How about if they talk dirty and/or call you names?
12- What’s your favorite food? What’s your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
If you win, what will you make them do?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
6- Do you have dreams? Can you remember them? What do you usually dream about?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
28- What are some things that people do that irritate you?
52~ What are your hobbies?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
3- Should Pluto still be considered a planet? 4- How about smoking?
3- What’s your favorite smell? Do you a least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
How many times do you think you have “made love”?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Repairman/Lonely Wife Virgin/Experienced
27- What was/ is nickname? Does it have a meaning behind it?
If you say it, I will stop, and we can talk about it when you are ready.
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
(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…)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
34~ Do you like the lights on or off during sex?
Doctor/Nurse Stripper/Client
42~ What’s your biggest regret in life?
1- What was your first impression of me? Has it changed?
7-What do I do in bed that drives you wild? How about, what turns you off?
Any that are a turn off?
21~ What was the best date you ever went on? What has been the worst?
19- What’s your favorite fairytale? What’s your least favorite?
How well do you know me? And some of your thoughts about me
36~ What is your favorite time of day to have sex/make love?
9- If you could have three wishes, what would they be? Why?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
83~ How do you feel about Porn?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Have you ever? 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.
40~ What’s the weirdest place you’ve ever had sex?
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?
31- If given a chance to be immortal, would you take it? Why?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
1- What’s your favorite animal? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How old are you? Male or Female?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
84~ How do you feel about reading/listening to adult stories?
Family Relation Age Play
Master/Slave Boss/Maid
Would you ever want to be woken up with oral and/or intercourse?
The Ice Breaker Questions
What was the longest? What was the shortest?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How many partners have you had oral sex with? Who? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
8- What are your thoughts on politics?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would you mind if your partner watched it? How about together vs alone?
76~ Have you had a threesome? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
Do you have a favorite? Is it ok if your partner does?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
33- Beach or Mountains? Or is there another place to like better?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
20- What’s your favorite candy? What’s your least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
10- What is your favorite family tradition? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, 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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
*** Deal Breaker Questions ***
80~ Share your top three fantasies/desires. (Be detailed) 😊
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,
22~ What is the best pickup line anyone has ever used on you? What was the worst?
26~ What side of the bed do you sleep on?
29- How superstitious are you?
39~ What are your love languages?
22- What is your favorite childhood memory? What is your least favorite?
Model/Photographer Police/Criminal
What is your favorite position? Why?
10~ How many dates are necessary before you to have sex with someone?
5- What do I do outside the bedroom that turns you on? How about, what turns you 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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
11- How about if they like a certain sports team? 12-How about drinking too much?
36- Do you play video games? What is your favorite? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?