What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 02:58
Would you ever want to be woken up with oral and/or intercourse?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
22- What is your favorite childhood memory? What is your least favorite?
How does someone start doing urban exploration?
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?
What have you learned about yourself that you did not before this?
19- What’s your favorite fairytale? What’s your least favorite?
6 Foods You Should Eat More of After 60, According to Dietitians - EatingWell
51~ What tends to bring a smile to your face?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12- What’s your favorite food? What’s your least favorite?
Meta Agreed to Pay up for Scale AI but Then Wanted More for Its Money - The Information
12- What is the weirdest thing you've ever eaten?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
17- Have you ever done drugs? Which ones? How often?
How do you go about getting invited to an orgy?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
19- Do/have you smoked? What do you prefer? How often?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
If you believe in God, do you think God can save you from cancer?
If you say it, I will stop, and we can talk about it when you are ready.
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?
Prisoner/Prison Guard Landlord/Tenant
Why are perceived or real slights interpreted as rejections and reality by pwBPD?
52~ What are your hobbies?
60~ How important is oral sex? Do you like receiving? Do you like giving?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Why do I feel sleepy after massage?
9- If you could have three wishes, what would they be? Why?
Would you read them together?
Will you cheat again? How can, you be sure? Define what cheating is to you.
How much should one budget to travel for 1 month generally?
10- What is your favorite family tradition? What’s your least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
92~ Everyone needs a “safe” word. What is yours?
Why do most Indian women cuckold or cheat on their husbands?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
3- What Superhero or Superpower would you want to be/have?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
New Pluto-Like Planet Discovered In Solar System — What To Know - Forbes
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
If you win, what will you make them do?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
13- What is the craziest/scariest thing you've ever done?
20- What’s your favorite candy? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
6- Do you have dreams? Can you remember them? What do you usually dream about?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
29- How superstitious are you?
11- How about if they like a certain sports team? 12-How about drinking too much?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What was the longest? What was the shortest?
*** Deal Breaker Questions ***
89~ Do you like taking showers together?
13~ Is there a difference between, making love, having sex, and fucking?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
62~ Have you used adult toys?
51~ Are you willing to play adult games with your partner?
40~ What’s the weirdest place you’ve ever had sex?
23- What is your dream job? What was it as a child?
34~ Do you like the lights on or off during sex?
Would you do it again, and would you rather 2 females or 2 males?
92~ Have you ever had or have an STD? How many? What was it?
Any that are a turn off?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Model/Photographer Police/Criminal
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Get this wrong and this could mean the end… :-) some funny, some not…
7-What do I do in bed that drives you wild? How about, what turns you off?
61~ How willing would you be to try new sexual positions?
Repairman/Lonely Wife Virgin/Experienced
Do you think this brought you closer together?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
67~ Do you like it when your partner moans and/or is vocal during sex?
29~ What are some things that turn you off? What is your biggest turn off?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Do you watch it? What is your favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
39~ What are your love languages?
Escort/Client Job Applicant/Hiring Manager
19~ Who/when was your first “heartbreak”?
Do you like it when they show and tell you what they want?
28- What are some things that people do that irritate you?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
30~ What's something unexpected that turns you on?
What have you learned about me that was new and/or surprising?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
28~ What are some things that turn on? What is your biggest turn on?
17- What’s your favorite holiday? What’s your 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.
*** What’s Your Favorite…? ***
What would you say to prove to yourself that it was really you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
48~ Do you have any siblings? Are you close to your family?
70~ Would/do you have/like anal sex?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How about if they talk dirty and/or call you names?
47~ What would be your dream job and why?
5~ When you first started having sex, was it what you thought it would be?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Family Relation Age Play
Does the thought excite you? Care to share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
27- What was/ is nickname? Does it have a meaning behind it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
* Give a rating for each one (0-100)
10~ How many dates are necessary before you to have sex with someone?
You know that I will be 100% truthful, so ask.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
25~ How do you feel about PDA? (Public Display of Affection)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
What do you dislike about me? I asked you to be 100% honest.
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
34- Ever been to a concert? What was your favorite? Who would you like to see?
(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…)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
10- List 5 of your top pet peeves.
13- What’s your favorite drink? What’s your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
52~ Are you willing to make “those types” of bets with your partner?
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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Any that are a turn off?
Would you mind if your partner watched it? How about together vs alone?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
I would allow you to do it… What would you do to me?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
9~ How many times over your lifetime do you think you have had sex so far?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Please share Did you stop?
31- If given a chance to be immortal, would you take it? Why?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
1- What was your first impression of me? Has it changed?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
*** Questions About Me ***
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
80~ Share your top three fantasies/desires. (Be detailed) 😊
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
21~ What was the best date you ever went on? What has been the worst?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- What’s your favorite smell? Do you a least favorite?
Over time has your thoughts on sex changed?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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?
18- How often do you drink alcohol? What is your favorite drink?
50~ How many children do you have? What are their ages?
82~ Do you have any fantasies involving Role-Playing?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Do you like the “69” position? Do you prefer to be on top or bottom?
9- What’s your favorite season and why? What’s your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
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…
Nothing too Serious
7- What are your thoughts on religion? Is there an afterlife?
30- Do you prefer living in the countryside, in a town, or in a big city? 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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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)
45~ How do you feel about me blindfolding you? How about blindfolding me?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
13- How about having a certain hair cut/style?
Would /have you ever given your partner a lap dance and Striptease?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Can you Deep Throat? Do you like the taste of yourself?
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,
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
83~ How do you feel about Porn?
81~ Do you have any kinks and/or fetishes?
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?
8- What are your thoughts on politics?
11- What's your favorite restaurant? What’s your least favorite?
Have you ever? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
36- Do you play video games? What is your favorite? Do you a least favorite?
21- What's your favorite way to spend a weekend or time off?
1~ How old were you when you had your first kiss? Who? Care to Share?
84~ How do you feel about reading/listening to adult stories?
44~ Care to share something about yourself that no one else knows about you?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
15- What bad habit do you wish you could quit? Do you have any addictions?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
38~ Share your most embarrassing sexual memory?
Nurse/Patient Celebrity/Fan
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
18~ Who/when was your first “crush”?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
The Ice Breaker Questions
How many times do you think you have “made love”?
48~ Have you ever paid or been paid for sex?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What is your favorite toy? Ever wanted to try a specific toy?
11- List at least 5 things on your bucket list. Have you done any of them already?
49~ How many times have you been married? Why did they end?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What is your favorite position? Why?
How old are you? Male or Female?
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?
11~ Have you ever been caught by your parents or children or others while having sex?
4- For a pet, Cat, dog or other?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Master/Slave Boss/Maid
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
If yes, what?
Do you have a favorite? Is it ok if your partner does?
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?
42~ What’s your biggest regret in life?
2- What’s your favorite color? Do you a least favorite?
1- What’s your favorite animal? Do you a least favorite?
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?
*** Random Questions ***
Teacher/Student Stranger/One Night Stand
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Doctor/Nurse Stripper/Client
33- Beach or Mountains? Or is there another place to like better?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
How well do you know me? And some of your thoughts about me
What is your view on sex? Meaning, When/Where/ How often/
37- Do you like your name? If you could change it, what would you change it too?
76~ Have you had a threesome? Care to Share?
32- What's your greatest talent? Can I see it right now?
14- What's your favorite dessert? Do you a least favorite?
*** Questions about Relationships/Past ***
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
That one or two things that made you go hmmmm, OMG or wow!
If NO, would you ever have one? Would it be with 2 men or 2 women?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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…