What is the most interesting question you can ask to get to know someone?
Last Updated: 18.06.2025 03:00
21~ What was the best date you ever went on? What has been the worst?
49~ How many times have you been married? Why did they end?
92~ Have you ever had or have an STD? How many? What was it?
It seems that I am cursed with bad luck. How do I break such a curse?
29~ What are some things that turn you off? What is your biggest turn off?
Would you allow me to clean every part of your body with my soapy hands and fingers?
If yes, what?
Is the Chinese economy currently collapsing? If not, what could potentially cause it to collapse?
15- What's your favorite saying? What word or phrase is your least favorite?
How old are you? Male or Female?
47~ What would be your dream job and why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
2- What’s your favorite color? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
What are my 10 favorite rock record album opening tracks?
33- If you could visit any time period, when would you pick? Please explain why?
Escort/Client Job Applicant/Hiring Manager
45~ How do you feel about me blindfolding you? How about blindfolding me?
What are some life hacks for living on your own?
11- List at least 5 things on your bucket list. Have you done any of them already?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
13- What is the craziest/scariest thing you've ever done?
Why do girls in Indian top colleges wear shorts?
If you win, what will you make them do?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
What does it mean when you dream that your mother died?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
40~ What’s the weirdest place you’ve ever had sex?
12- What is the weirdest thing you've ever eaten?
What do porn stars do when they get old?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
60~ How important is oral sex? Do you like receiving? Do you like giving?
*** Deal Breaker 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,
92~ Everyone needs a “safe” word. What is yours?
9- If you could have three wishes, what would they be? Why?
If you were a writer for HBO, how would you rewrite the final season of Game of Thrones?
13- What’s your favorite drink? What’s your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
11- How about if they like a certain sports team? 12-How about drinking too much?
Do you wear tights for warmth or to make your legs look better?
20- What’s your favorite candy? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
37- Do you like your name? If you could change it, what would you change it too?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Why does cocaine makes me want to dress up and get fuck
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Please share Did you stop?
*** Questions About Me ***
What's your take on Eternal Sunshine of the Spotless Mind? How has it affected you?
How many times do you think you have “made love”?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you do it again, and would you rather 2 females or 2 males?
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
14- What is an embarrassing moment in your life? How about your most embarrassing?
* Give a rating for each one (0-100)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
44~ Care to share something about yourself that no one else knows about you?
18~ Who/when was your first “crush”?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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)
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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Have you ever? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
15~ Have you ever been “in love”? Who? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If you say it, I will stop, and we can talk about it when you are ready.
48~ Do you have any siblings? Are you close to your family?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
8- What are your thoughts on politics?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
You know that I will be 100% truthful, so ask.
13- How about having a certain hair cut/style?
14- What's your favorite dessert? Do you a least favorite?
4- For a pet, Cat, dog or other?
53~ How much can you tell me about the one thing you are most passionate about?
Will you cheat again? How can, you be sure? Define what cheating is to you.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9- Is there something you’ve always wanted to ask me but you’re afraid?
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?
12- What’s your favorite food? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
10- List 5 of your top pet peeves.
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?
3- What’s your favorite smell? Do you a least favorite?
62~ Have you used adult toys?
What is your favorite position? Why?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What do you dislike about me? I asked you to be 100% honest.
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
5~ When you first started having sex, was it what you thought it would be?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
50~ How many children do you have? What are their ages?
Would you ever want to be woken up with oral and/or intercourse?
What have you learned about me that was new and/or surprising?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
34~ Do you like the lights on or off during sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
89~ Do you like taking showers together?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
If YES, was it with 2 men or 2 women? Did you enjoy it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
82~ Do you have any fantasies involving Role-Playing?
6- Do you have dreams? Can you remember them? What do you usually dream about?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
What is your view on sex? Meaning, When/Where/ How often/
21- What's your favorite way to spend a weekend or time off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
83~ How do you feel about Porn?
Do you think this brought you closer together?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
42~ What’s your biggest regret in life?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Do you have a favorite? Is it ok if your partner does?
61~ How willing would you be to try new sexual positions?
9~ How many times over your lifetime do you think you have had sex so far?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What was the longest? What was the shortest?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
18- How often do you drink alcohol? What is your favorite drink?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
19- What’s your favorite fairytale? What’s your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
7- What if a person smells a certain way? 8- How about smoking?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
1- What’s your favorite animal? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
3- Should Pluto still be considered a planet? 4- How about smoking?
Prisoner/Prison Guard Landlord/Tenant
32- What's your greatest talent? Can I see it right now?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Doctor/Nurse Stripper/Client
*** Questions about Relationships/Past ***
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Do you like the “69” position? Do you prefer to be on top or bottom?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
52~ Are you willing to make “those types” of bets with your partner?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
36- Do you play video games? What is your favorite? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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?
51~ Are you willing to play adult games with your partner?
Would you mind if your partner watched it? How about together vs alone?
7-What do I do in bed that drives you wild? How about, what turns you off?
That one or two things that made you go hmmmm, OMG or wow!
48~ Have you ever paid or been paid for sex?
What is your favorite toy? Ever wanted to try a specific toy?
How well do you know me? And some of your thoughts about me
Any that are a turn off?
10~ How many dates are necessary before you to have sex with someone?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
22- Do you have any birth marks? How about scars? Care to share how you got them?
29- How superstitious are you?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? 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.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Repairman/Lonely Wife Virgin/Experienced
Master/Slave Boss/Maid
The Ice Breaker Questions
Family Relation Age Play
36~ What is your favorite time of day to have sex/make love?
Any that are a turn off?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
28~ What are some things that turn on? What is your biggest turn on?
Do you like it when they show and tell you what they want?
Get this wrong and this could mean the end… :-) some funny, some not…
1~ How old were you when you had your first kiss? Who? Care to Share?
19~ Who/when was your first “heartbreak”?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
33- Beach or Mountains? Or is there another place to like better?
Model/Photographer Police/Criminal
3- What Superhero or Superpower would you want to be/have?
17- What’s your favorite holiday? What’s your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
How many partners have you had oral sex with? Who? Care to Share?
52~ What are your hobbies?
70~ Would/do you have/like anal sex?
(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…)
*** Random Questions ***
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Nothing too Serious
Teacher/Student Stranger/One Night Stand
7- What are your thoughts on religion? Is there an afterlife?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
*** What’s Your Favorite…? ***
30~ What's something unexpected that turns you on?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
34- Ever been to a concert? What was your favorite? Who would you like to see?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
22- What is your favorite childhood memory? What is your least favorite?
What have you learned about yourself that you did not before this?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
I would allow you to do it… What would you do to me?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
How about if they talk dirty and/or call you names?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
9- What’s your favorite season and why? What’s your least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
23- What is your dream job? What was it as a child?
Does the thought excite you? Care to share?
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…
Do you watch it? What is your favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
26~ What side of the bed do you sleep on?
76~ Have you had a threesome? Care to Share?
What would you say to prove to yourself that it was really you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
17- Have you ever done drugs? Which ones? How often?
15- What bad habit do you wish you could quit? Do you have any addictions?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
81~ Do you have any kinks and/or fetishes?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
10- What is your favorite family tradition? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
11- What's your favorite restaurant? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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…
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?
Would you read them together?
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?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
51~ What tends to bring a smile to your face?
27- What was/ is nickname? Does it have a meaning behind it?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Can you Deep Throat? Do you like the taste of yourself?
19- Do/have you smoked? What do you prefer? How often?
1- What was your first impression of me? Has it changed?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
28- What are some things that people do that irritate you?
31- If given a chance to be immortal, would you take it? Why?
Nurse/Patient Celebrity/Fan
Over time has your thoughts on sex changed?
38~ Share your most embarrassing sexual memory?
56~ Would you ever go to a strip club 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?