What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 23:59
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Would you allow me to clean every part of your body with my soapy hands and fingers?
70~ Would/do you have/like anal sex?
Swarms of tiny robots could go up your nose, melt the mucus and clean your sinuses - ZME Science
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
20- What’s your favorite candy? What’s your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
Is it true that most Indian men are gay and they just hide their feelings?
11- List at least 5 things on your bucket list. Have you done any of them already?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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…
Why am I attracted to older men?
12- What is the weirdest thing you've ever eaten?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
What are some effective ways to cope with loss and grief?
Do you like the “69” position? Do you prefer to be on top or bottom?
17- Have you ever done drugs? Which ones? How often?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What are the bitter truths of life one should know?
If YES, was it with 2 men or 2 women? Did you enjoy it?
5- Have you ever been hypnotized? Would you allow yourself to be?
36- Do you play video games? What is your favorite? Do you a least favorite?
GameStop promise replacements after retail staff staples Switch 2 screens - OC3D
29- How superstitious are you?
30~ What's something unexpected that turns you on?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
10- List 5 of your top pet peeves.
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…
15- What bad habit do you wish you could quit? Do you have any addictions?
How well do you know me? And some of your thoughts about me
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If it weren't for your ult, which group would be your ult?
Will you cheat again? How can, you be sure? Define what cheating is to you.
* Give a rating for each one (0-100)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
23- What is your dream job? What was it as a child?
25~ How do you feel about PDA? (Public Display of Affection)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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 are the gifts you got when you cleared JEE ?
9- What’s your favorite season and why? What’s your least favorite?
If yes, what?
14- What is an embarrassing moment in your life? How about your most embarrassing?
7~ How many times in one day have you had sex? Who/When/Where? 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?
If you win, what will you make them do?
14- What's your favorite dessert? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Would you do it again, and would you rather 2 females or 2 males?
36~ What is your favorite time of day to have sex/make love?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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)
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?
13~ Is there a difference between, making love, having sex, and fucking?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
7- What if a person smells a certain way? 8- How about smoking?
26~ What side of the bed do you sleep on?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
(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…)
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?
Escort/Client Job Applicant/Hiring Manager
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
If NO, would you ever have one? Would it be with 2 men or 2 women?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
61~ How willing would you be to try new sexual positions?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
19- What’s your favorite fairytale? What’s your least favorite?
89~ Do you like taking showers together?
2- What’s your favorite color? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Does the thought excite you? Care to share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
71~ Would you give your partner a hand or foot job? Would you receive one?
3- Should Pluto still be considered a planet? 4- How about smoking?
11~ Have you ever been caught by your parents or children or others while having sex?
What have you learned about me that was new and/or surprising?
Do you like it when they show and tell you what they want?
What is your favorite toy? Ever wanted to try a specific toy?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
52~ What are your hobbies?
32- What's your greatest talent? Can I see it right now?
8- What's your favorite flavor of ice cream? Do you a least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Model/Photographer Police/Criminal
11- What's your favorite restaurant? 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?
65~ Describe the best orgasm you’ve ever had? Care to share?
7- What are your thoughts on religion? Is there an afterlife?
Nurse/Patient Celebrity/Fan
What is your view on sex? Meaning, When/Where/ How often/
Do you have a favorite? Is it ok if your partner does?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
40~ What’s the weirdest place you’ve ever had sex?
What do you dislike about me? I asked you to be 100% honest.
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you ever want to be woken up with oral and/or intercourse?
28~ What are some things that turn on? What is your biggest turn on?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
That one or two things that made you go hmmmm, OMG or wow!
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
29~ What are some things that turn you off? What is your biggest turn off?
50~ How many children do you have? What are their ages?
*** Random Questions ***
62~ Have you used adult toys?
*** Deal Breaker Questions ***
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
15~ Have you ever been “in love”? Who? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your favorite animal? Do you a least favorite?
Please share Did you stop?
27- What was/ is nickname? Does it have a meaning behind it?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
*** Questions About Me ***
48~ Do you have any siblings? Are you close to your family?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
60~ How important is oral sex? Do you like receiving? Do you like giving?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
22- What is your favorite childhood memory? What is your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
51~ Are you willing to play adult games with your partner?
How many times do you think you have “made love”?
Can you Deep Throat? Do you like the taste of yourself?
How about if they talk dirty and/or call you names?
Teacher/Student Stranger/One Night Stand
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
You know that I will be 100% truthful, so ask.
37- Do you like your name? If you could change it, what would you change it too?
Any that are a turn off?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Family Relation Age Play
Have you ever? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
81~ Do you have any kinks and/or fetishes?
5~ When you first started having sex, was it what you thought it would be?
28- What are some things that people do that irritate you?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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,
Get this wrong and this could mean the end… :-) some funny, some not…
What have you learned about yourself that you did not before this?
47~ What would be your dream job and why?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Do you watch it? What is your favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Would you mind if your partner watched it? How about together vs alone?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
8- What are your thoughts on politics?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
How many partners have you had oral sex with? Who? Care to Share?
Nothing too Serious
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
48~ Have you ever paid or been paid for sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Do you think this brought you closer together?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
1- What was your first impression of me? Has it changed?
84~ How do you feel about reading/listening to adult stories?
*** What’s Your Favorite…? ***
What would you say to prove to yourself that it was really you?
39~ What are your love languages?
10- What is your favorite family tradition? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
4- For a pet, Cat, dog or other?
13- How about having a certain hair cut/style?
Would you read them together?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Repairman/Lonely Wife Virgin/Experienced
49~ How many times have you been married? Why did they end?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
13- What is the craziest/scariest thing you've ever done?
15- What's your favorite saying? What word or phrase is your least favorite?
3- What Superhero or Superpower would you want to be/have?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
The Ice Breaker Questions
Master/Slave Boss/Maid
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
9- If you could have three wishes, what would they be? Why?
9~ How many times over your lifetime do you think you have had sex so far?
Prisoner/Prison Guard Landlord/Tenant
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
67~ Do you like it when your partner moans and/or is vocal during sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
11- How about if they like a certain sports team? 12-How about drinking too much?
How old are you? Male or Female?
42~ What’s your biggest regret in life?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
92~ Everyone needs a “safe” word. What is yours?
21~ What was the best date you ever went on? What has been the worst?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
31- If given a chance to be immortal, would you take it? Why?
What was the longest? What was the shortest?
34~ Do you like the lights on or off during sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
51~ What tends to bring a smile to your face?
76~ Have you had a threesome? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
If you say it, I will stop, and we can talk about it when you are ready.
18- How often do you drink alcohol? What is your favorite drink?
9- Is there something you’ve always wanted to ask me but you’re afraid?
13- What’s your favorite drink? What’s your least favorite?
21- What's your favorite way to spend a weekend or time off?
Would /have you ever given your partner a lap dance and Striptease?
33- Beach or Mountains? Or is there another place to like better?
What is your favorite position? Why?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
53~ How much can you tell me about the one thing you are most passionate about?
*** Questions about Relationships/Past ***
33- If you could visit any time period, when would you pick? Please explain why?
17- What’s your favorite holiday? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
52~ Are you willing to make “those types” of bets with your partner?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
44~ Care to share something about yourself that no one else knows about you?
19~ Who/when was your first “heartbreak”?
38~ Share your most embarrassing sexual memory?
22- Do you have any birth marks? How about scars? Care to share how you got them?
10~ How many dates are necessary before you to have sex with someone?
83~ How do you feel about Porn?
Doctor/Nurse Stripper/Client
80~ Share your top three fantasies/desires. (Be detailed) 😊
Any that are a turn off?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Over time has your thoughts on sex changed?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
18~ Who/when was your first “crush”?
19- Do/have you smoked? What do you prefer? How often?
I would allow you to do it… What would you do to me?