What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 03:13
Would you ever want to be woken up with oral and/or intercourse?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
32- What's your greatest talent? Can I see it right now?
How do we write and pronounce "it's my pleasure" in Italian?
40~ What’s the weirdest place you’ve ever had sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Isn’t freedom of speech and expression an absolute right?
52~ What are your hobbies?
Over time has your thoughts on sex changed?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
1- What was your first impression of me? Has it changed?
*** Deal Breaker Questions ***
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What are some cool confidence hacks?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What's your favourite porn video to jerk off to?
15~ Have you ever been “in love”? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
Do you know of a female masseuse that does door-to-door service in Bangalore?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
47~ What would be your dream job and why?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Is using tech to track or monitor your partner’s activities a sign of love, insecurity, or control?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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?
Why are white women dating more black guys than ever?
You know that I will be 100% truthful, so ask.
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 you win, what will you make them do?
If yes, what?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What celebrity do you admire the most?
11~ Have you ever been caught by your parents or children or others while having sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
11- What's your favorite restaurant? What’s your least favorite?
Why should we share our wife with others?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
*** What’s Your Favorite…? ***
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How do I run away? I'm 15 and live in Oklahoma.
Teacher/Student Stranger/One Night Stand
1~ How old were you when you had your first kiss? Who? Care to Share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Why is it easy to make money in the USA?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
21- What's your favorite way to spend a weekend or time off?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
What was your best sex experience that still makes you horny?
7-What do I do in bed that drives you wild? How about, what turns you off?
13- What is the craziest/scariest thing you've ever done?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Google’s Gemini AI will summarize PDFs for you when you open them - The Verge
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
How many partners have you had oral sex with? Who? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
10- What is your favorite family tradition? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What is your favorite toy? Ever wanted to try a specific toy?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
The Ice Breaker Questions
9- If you could have three wishes, what would they be? Why?
30~ What's something unexpected that turns you on?
14- What is an embarrassing moment in your life? How about your most embarrassing?
81~ Do you have any kinks and/or fetishes?
How many times do you think you have “made love”?
How about if they talk dirty and/or call you names?
61~ How willing would you be to try new sexual positions?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Escort/Client Job Applicant/Hiring Manager
36~ What is your favorite time of day to have sex/make love?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What would you say to prove to yourself that it was really you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
What was the longest? What was the shortest?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
29~ What are some things that turn you off? What is your biggest turn off?
Will you cheat again? How can, you be sure? Define what cheating is to you.
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Would you do it again, and would you rather 2 females or 2 males?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
26~ What side of the bed do you sleep on?
Any that are a turn off?
13~ Is there a difference between, making love, having sex, and fucking?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
5~ When you first started having sex, was it what you thought it would be?
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?
49~ How many times have you been married? Why did they end?
34~ Do you like the lights on or off during sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
10~ How many dates are necessary before you to have sex with someone?
Family Relation Age Play
Will you kiss after your partner has gone down on you? Swallow or spit semen?
8- What's your favorite flavor of ice cream? Do you a least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Doctor/Nurse Stripper/Client
28~ What are some things that turn on? What is your biggest turn on?
Would you mind if your partner watched it? How about together vs alone?
14- What's your favorite dessert? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
1- What’s your favorite animal? Do you a least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
19~ Who/when was your first “heartbreak”?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
7- What if a person smells a certain way? 8- How about smoking?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
83~ How do you feel about Porn?
5- Have you ever been hypnotized? Would you allow yourself to be?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
33- If you could visit any time period, when would you pick? Please explain why?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
I would allow you to do it… What would you do to me?
What have you learned about yourself that you did not before this?
Would /have you ever given your partner a lap dance and Striptease?
92~ Everyone needs a “safe” word. What is yours?
13- How about having a certain hair cut/style?
Does the thought excite you? Care to share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
11- List at least 5 things on your bucket list. Have you done any of them already?
15- What bad habit do you wish you could quit? Do you have any addictions?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Nothing too Serious
34- Ever been to a concert? What was your favorite? Who would you like to see?
18- How often do you drink alcohol? What is your favorite drink?
51~ Are you willing to play adult games with your partner?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What do you dislike about me? I asked you to be 100% honest.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
25~ How do you feel about PDA? (Public Display of Affection)
That one or two things that made you go hmmmm, OMG or wow!
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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?
76~ Have you had a threesome? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
70~ Would/do you have/like anal sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
3- What Superhero or Superpower would you want to be/have?
9- Is there something you’ve always wanted to ask me but you’re afraid?
38~ Share your most embarrassing sexual memory?
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
82~ Do you have any fantasies involving Role-Playing?
67~ Do you like it when your partner moans and/or is vocal during sex?
Repairman/Lonely Wife Virgin/Experienced
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
How old are you? Male or Female?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
53~ How much can you tell me about the one thing you are most passionate about?
11- How about if they like a certain sports team? 12-How about drinking too much?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
How well do you know me? And some of your thoughts about me
28- What are some things that people do that irritate you?
39~ What are your love languages?
3- What’s your favorite smell? Do you a least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
89~ Do you like taking showers together?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
10- List 5 of your top pet peeves.
Would you allow me to clean every part of your body with my soapy hands and fingers?
50~ How many children do you have? What are their ages?
22- Do you have any birth marks? How about scars? Care to share how you got them?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
31- If given a chance to be immortal, would you take it? Why?
17- What’s your favorite holiday? What’s your least favorite?
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?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
19- Do/have you smoked? What do you prefer? How often?
84~ How do you feel about reading/listening to adult stories?
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Have you ever? Care to Share?
2- What’s your favorite color? Do you a least favorite?
* Give a rating for each one (0-100)
42~ What’s your biggest regret in life?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
12- What is the weirdest thing you've ever eaten?
What is your favorite position? Why?
7- What are your thoughts on religion? Is there an afterlife?
*** Questions About Me ***
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
Do you watch it? What is your favorite?
Please share Did you stop?
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?
48~ Do you have any siblings? Are you close to your family?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
37- Do you like your name? If you could change it, what would you change it too?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you like the “69” position? Do you prefer to be on top or bottom?
Do you have a favorite? Is it ok if your partner does?
92~ Have you ever had or have an STD? How many? What was it?
Model/Photographer Police/Criminal
51~ What tends to bring a smile to your face?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Do you like it when they show and tell you what they want?
45~ How do you feel about me blindfolding you? How about blindfolding me?
8- What are your thoughts on politics?
18~ Who/when was your first “crush”?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
4- For a pet, Cat, dog or other?
What is your view on sex? Meaning, When/Where/ How often/
20- What’s your favorite candy? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
13- What’s your favorite drink? What’s your least favorite?
*** Random Questions ***
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,
33- Beach or Mountains? Or is there another place to like better?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you think this brought you closer together?
9~ How many times over your lifetime do you think you have had sex so far?
Would you read them together?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
21~ What was the best date you ever went on? What has been the worst?
12- What’s your favorite food? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
Any that are a turn off?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
29- How superstitious are you?
If you say it, I will stop, and we can talk about it when you are ready.
17- Have you ever done drugs? Which ones? How often?
9- What’s your favorite season and why? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
22- What is your favorite childhood memory? What is your least favorite?
Can you Deep Throat? Do you like the taste of yourself?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Nurse/Patient Celebrity/Fan
80~ Share your top three fantasies/desires. (Be detailed) 😊
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
23- What is your dream job? What was it as a child?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
15- What's your favorite saying? What word or phrase is your least favorite?
Master/Slave Boss/Maid
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…
(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…)
What have you learned about me that was new and/or surprising?
62~ Have you used adult toys?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
*** Questions about Relationships/Past ***
44~ Care to share something about yourself that no one else knows about you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…