What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 00:23
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
17- What’s your favorite holiday? What’s your least favorite?
*** Questions about Relationships/Past ***
Do Indian guys like African girls?
What is your favorite position? Why?
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?
4- For a pet, Cat, dog or other?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
You May Want To Think Twice Before You Eat Bagged Lettuce - HuffPost
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
If you say it, I will stop, and we can talk about it when you are ready.
When you visit a store, do you go to shop or buy?
65~ Describe the best orgasm you’ve ever had? Care to share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
8- What's your favorite flavor of ice cream? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
26~ What side of the bed do you sleep on?
*** Questions About Me ***
Who are some of the best Korean Actresses?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
23- What is your dream job? What was it as a child?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Over time has your thoughts on sex changed?
What one thing makes someone a very mature person?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
7-What do I do in bed that drives you wild? How about, what turns you off?
Teacher/Student Stranger/One Night Stand
Creatine for the brain: How this workout supplement supercharges memory and focus - Times of India
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How many partners have you had oral sex with? Who? Care to Share?
What was your most memorable experience catching a fraudulent car seller?
3- What Superhero or Superpower would you want to be/have?
18~ Who/when was your first “crush”?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
How old are you? Male or Female?
Does the thought excite you? Care to share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
I just cannot wake up early, even if I sleep on time. What should I do?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Why is my crush beautiful to me but not to others?
* Give a rating for each one (0-100)
12- What is the weirdest thing you've ever eaten?
Would you allow me to clean every part of your body with my soapy hands and fingers?
What is the reason behind some people wearing trunks instead of speedos when swimming in pools?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
22- Do you have any birth marks? How about scars? Care to share how you got them?
5- Have you ever been hypnotized? Would you allow yourself to be?
25~ How do you feel about PDA? (Public Display of Affection)
3- Should Pluto still be considered a planet? 4- How about smoking?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
13~ Is there a difference between, making love, having sex, and fucking?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
7- What if a person smells a certain way? 8- How about smoking?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
*** What’s Your Favorite…? ***
38~ Share your most embarrassing sexual memory?
If yes, what?
Would you ever want to be woken up with oral and/or intercourse?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
8- What are your thoughts on politics?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
21~ What was the best date you ever went on? What has been the worst?
22- What is your favorite childhood memory? What is your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
34~ Do you like the lights on or off during 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?
10- What is your favorite family tradition? What’s your least favorite?
39~ What are your love languages?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Please share Did you stop?
What would you say to prove to yourself that it was really you?
How about if they talk dirty and/or call you names?
3- What’s your favorite smell? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
49~ How many times have you been married? Why did they end?
17- Have you ever done drugs? Which ones? How often?
51~ Are you willing to play adult games with your partner?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Do you like the “69” position? Do you prefer to be on top or bottom?
If NO, would you ever have one? Would it be with 2 men or 2 women?
89~ Do you like taking showers together?
If you win, what will you make them do?
61~ How willing would you be to try new sexual positions?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
28~ What are some things that turn on? What is your biggest turn on?
42~ What’s your biggest regret in life?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
76~ Have you had a threesome? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
*** Deal Breaker Questions ***
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
48~ Have you ever paid or been paid for sex?
82~ Do you have any fantasies involving Role-Playing?
29- How superstitious are you?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
37- Do you like your name? If you could change it, what would you change it too?
80~ Share your top three fantasies/desires. (Be detailed) 😊
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
50~ How many children do you have? What are their ages?
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)
I would allow you to do it… What would you do to me?
Model/Photographer Police/Criminal
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Nothing too Serious
11- What's your favorite restaurant? What’s your least favorite?
70~ Would/do you have/like anal sex?
19- Do/have you smoked? What do you prefer? How often?
What is your view on sex? Meaning, When/Where/ How often/
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
That one or two things that made you go hmmmm, OMG or wow!
12- What’s your favorite food? What’s your least favorite?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Would you do it again, and would you rather 2 females or 2 males?
45~ How do you feel about me blindfolding you? How about blindfolding me?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
9- If you could have three wishes, what would they be? Why?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
How well do you know me? And some of your thoughts about me
The Ice Breaker Questions
7- What are your thoughts on religion? Is there an afterlife?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
*** Random Questions ***
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What was the longest? What was the shortest?
51~ What tends to bring a smile to your face?
53~ How much can you tell me about the one thing you are most passionate about?
Can you Deep Throat? Do you like the taste of yourself?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would /have you ever given your partner a lap dance and Striptease?
27- What was/ is nickname? Does it have a meaning behind it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
18- How often do you drink alcohol? What is your favorite drink?
Prisoner/Prison Guard Landlord/Tenant
Repairman/Lonely Wife Virgin/Experienced
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
11- List at least 5 things on your bucket list. Have you done any of them already?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
83~ How do you feel about Porn?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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?
Would you mind if your partner watched it? How about together vs alone?
15- What bad habit do you wish you could quit? Do you have any addictions?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Nurse/Patient Celebrity/Fan
81~ Do you have any kinks and/or fetishes?
32- What's your greatest talent? Can I see it right now?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
36- Do you play video games? What is your favorite? Do you a least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How many times do you think you have “made love”?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
13- What’s your favorite drink? What’s your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
62~ Have you used adult toys?
Family Relation Age Play
48~ Do you have any siblings? Are you close to your family?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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…
5~ When you first started having sex, was it what you thought it would be?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
10~ How many dates are necessary before you to have sex with someone?
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?
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…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
1- What was your first impression of me? Has it changed?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
47~ What would be your dream job and why?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
1- What’s your favorite animal? Do you a least favorite?
Doctor/Nurse Stripper/Client
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.
13- What is the craziest/scariest thing you've ever done?
What have you learned about yourself that you did not before this?
92~ Have you ever had or have an STD? How many? What was it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Have you ever? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
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?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
44~ Care to share something about yourself that no one else knows about you?
15~ Have you ever been “in love”? Who? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
14- What's your favorite dessert? Do you a least favorite?
Master/Slave Boss/Maid
33- If you could visit any time period, when would you pick? Please explain why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
30~ What's something unexpected that turns you on?
20- What’s your favorite candy? What’s your least favorite?
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…
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Do you watch it? What is your favorite?
10- List 5 of your top pet peeves.
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Escort/Client Job Applicant/Hiring Manager
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
52~ What are your hobbies?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
13- How about having a certain hair cut/style?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
11- How about if they like a certain sports team? 12-How about drinking too much?
What is your favorite toy? Ever wanted to try a specific toy?
36~ What is your favorite time of day to have sex/make love?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
2- What’s your favorite color? Do you a least favorite?
Any that are a turn off?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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,
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?
28- What are some things that people do that irritate you?
What do you dislike about me? I asked you to be 100% honest.
Do you like it when they show and tell you what they want?
84~ How do you feel about reading/listening to adult stories?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
You know that I will be 100% truthful, so ask.
Any that are a turn off?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
11~ Have you ever been caught by your parents or children or others while having sex?
Would you read them together?
68~ Would you ever get your partner up from bed by using oral sex 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?
19- What’s your favorite fairytale? What’s your least favorite?
Do you think this brought you closer together?
33- Beach or Mountains? Or is there another place to like better?
What have you learned about me that was new and/or surprising?
92~ Everyone needs a “safe” word. What is yours?
19~ Who/when was your first “heartbreak”?