What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 03:58
If you say it, I will stop, and we can talk about it when you are ready.
31- If given a chance to be immortal, would you take it? Why?
*** Questions about Relationships/Past ***
Do you suck dicks with no reciprocation?
Would /have you ever given your partner a lap dance and Striptease?
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…
What have you learned about me that was new and/or surprising?
Do most narcissists have good intentions as long as you are under their control?
Would you read them together?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
What is your review of Hartley`s High School, Kolkata?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
18~ Who/when was your first “crush”?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Why do narcissists devour so much sugar (candy, ice cream, donuts, etc., in huge amounts at a time)?
28- What are some things that people do that irritate you?
Have you ever? Care to Share?
Any that are a turn off?
What is a good tool for product analytics besides Google Analytics?
84~ How do you feel about reading/listening to adult stories?
Do you think this brought you closer together?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
8 of the most controversial album covers of all time - dazeddigital.com
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
11- What's your favorite restaurant? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How do you handle your mother-in-law after you heard her talking badly about you in the next room?
22- What is your favorite childhood memory? What is your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
51~ Are you willing to play adult games with your partner?
What symptoms did you notice before being diagnosed with cancer?
67~ Do you like it when your partner moans and/or is vocal during sex?
10- List 5 of your top pet peeves.
What is your favorite position? Why?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
*** Deal Breaker Questions ***
Master/Slave Boss/Maid
What are some ways to cope with paranoid thoughts about being gangstalked or targeted individuals?
18- How often do you drink alcohol? What is your favorite drink?
8- What are your thoughts on politics?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Brad Pitt Wears a Cobalt Blue Velvet Blazer and Barrel Jeans with Ines de Ramon - instyle.com
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
What was the longest? What was the shortest?
3- What’s your favorite smell? Do you a least favorite?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
50~ How many children do you have? What are their ages?
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…
Nurse/Patient Celebrity/Fan
64~ When was your very first orgasm? When was your first from having sex? Care to share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
14- What is an embarrassing moment in your life? How about your most embarrassing?
60~ How important is oral sex? Do you like receiving? Do you like giving?
65~ Describe the best orgasm you’ve ever had? Care to share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
How about if they talk dirty and/or call you names?
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?
Would you ever want to be woken up with oral and/or intercourse?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
32- What's your greatest talent? Can I see it right now?
If yes, what?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you have a favorite? Is it ok if your partner does?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
29- How superstitious are you?
9- If you could have three wishes, what would they be? Why?
36~ What is your favorite time of day to have sex/make love?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Repairman/Lonely Wife Virgin/Experienced
80~ Share your top three fantasies/desires. (Be detailed) 😊
76~ Have you had a threesome? Care to Share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
92~ Everyone needs a “safe” word. What is yours?
I would allow you to do it… What would you do to me?
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?
19- What’s your favorite fairytale? What’s your least favorite?
23- What is your dream job? What was it as a child?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Family Relation Age Play
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
15~ Have you ever been “in love”? Who? Care to Share?
Model/Photographer Police/Criminal
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
13- How about having a certain hair cut/style?
Any that are a turn off?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
* Give a rating for each one (0-100)
3- What Superhero or Superpower would you want to be/have?
(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…)
13~ Is there a difference between, making love, having sex, and fucking?
Please share Did you stop?
Teacher/Student Stranger/One Night Stand
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
83~ How do you feel about Porn?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
What would you say to prove to yourself that it was really you?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
11- How about if they like a certain sports team? 12-How about drinking too much?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Can you Deep Throat? Do you like the taste of yourself?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
29~ What are some things that turn you off? What is your biggest turn off?
34~ Do you like the lights on or off during sex?
39~ What are your love languages?
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?
14- What's your favorite dessert? Do you a least favorite?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What is your view on sex? Meaning, When/Where/ How often/
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
81~ Do you have any kinks and/or fetishes?
*** Random Questions ***
89~ Do you like taking showers together?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
7- What are your thoughts on religion? Is there an afterlife?
10- What is your favorite family tradition? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
33- Beach or Mountains? Or is there another place to like better?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
17- Have you ever done drugs? Which ones? How often?
51~ What tends to bring a smile to your face?
7-What do I do in bed that drives you wild? How about, what turns you off?
52~ Are you willing to make “those types” of bets with your partner?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
17- What’s your favorite holiday? What’s your least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
34- Ever been to a concert? What was your favorite? Who would you like to see?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
*** Questions About Me ***
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How many times do you think you have “made love”?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
9~ How many times over your lifetime do you think you have had sex so far?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
8- What's your favorite flavor of ice cream? Do you a least favorite?
12- What’s your favorite food? What’s your least favorite?
61~ How willing would you be to try new sexual positions?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you like it when they show and tell you what they want?
11~ Have you ever been caught by your parents or children or others while having 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?
Would you mind if your partner watched it? How about together vs alone?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
11- List at least 5 things on your bucket list. Have you done any of them already?
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)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
4- For a pet, Cat, dog or other?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Do you watch it? What is your favorite?
48~ Have you ever paid or been paid for sex?
12- What is the weirdest thing you've ever eaten?
If NO, would you ever have one? Would it be with 2 men or 2 women?
13- What is the craziest/scariest thing you've ever done?
54~ Would you ever go skinny dipping with your partner? Have you ever been? 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?
27- What was/ is nickname? Does it have a meaning behind it?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
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?
That one or two things that made you go hmmmm, OMG or wow!
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?
20- What’s your favorite candy? What’s your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
*** What’s Your Favorite…? ***
40~ What’s the weirdest place you’ve ever had sex?
What is your favorite toy? Ever wanted to try a specific toy?
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?
33- If you could visit any time period, when would you pick? Please explain why?
1- What was your first impression of me? Has it changed?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Nothing too Serious
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
28~ What are some things that turn on? What is your biggest turn on?
6- Do you have dreams? Can you remember them? What do you usually dream about?
5- Have you ever been hypnotized? Would you allow yourself to be?
1~ How old were you when you had your first kiss? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
19~ Who/when was your first “heartbreak”?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
2- What’s your favorite color? Do you a least favorite?
What do you dislike about me? I asked you to be 100% honest.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How old are you? Male or Female?
Prisoner/Prison Guard Landlord/Tenant
Escort/Client Job Applicant/Hiring Manager
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
37- Do you like your name? If you could change it, what would you change it too?
62~ Have you used adult toys?
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?
15- What bad habit do you wish you could quit? Do you have any addictions?
47~ What would be your dream job and why?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
5~ When you first started having sex, was it what you thought it would be?
9- Is there something you’ve always wanted to ask me but you’re afraid?
How well do you know me? And some of your thoughts about me
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
92~ Have you ever had or have an STD? How many? What was it?
30~ What's something unexpected that turns you on?
9- What’s your favorite season and why? What’s your least favorite?
49~ How many times have you been married? Why did they end?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
26~ What side of the bed do you sleep on?
15- What's your favorite saying? What word or phrase is your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
If YES, was it with 2 men or 2 women? Did you enjoy it?
21- What's your favorite way to spend a weekend or time off?
The Ice Breaker Questions
You know that I will be 100% truthful, so ask.
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?
How many partners have you had oral sex with? Who? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
What have you learned about yourself that you did not before this?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Would you do it again, and would you rather 2 females or 2 males?
38~ Share your most embarrassing sexual memory?
1- What’s your favorite animal? Do you a least favorite?
52~ What are your hobbies?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you like the “69” position? Do you prefer to be on top or bottom?
71~ Would you give your partner a hand or foot job? Would you receive one?
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,
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
If you win, what will you make them do?
36- Do you play video games? What is your favorite? Do you a least favorite?
21~ What was the best date you ever went on? What has been the worst?
Doctor/Nurse Stripper/Client
Will you kiss after your partner has gone down on you? Swallow or spit semen?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
48~ Do you have any siblings? Are you close to your family?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
70~ Would/do you have/like anal sex?
25~ How do you feel about PDA? (Public Display of Affection)
Over time has your thoughts on sex changed?