What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 00:11
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
32- What's your greatest talent? Can I see it right now?
What is your favorite position? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Why do many Hong Kong Chinese look different from the Han Chinese in mainland China?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
18~ Who/when was your first “crush”?
Would you do it again, and would you rather 2 females or 2 males?
What is a good habit and what is bad one?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
33- Beach or Mountains? Or is there another place to like better?
Have you ever? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
83~ How do you feel about Porn?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
34~ Do you like the lights on or off during sex?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
How many partners have you had oral sex with? Who? Care to Share?
Has anyone shared his wife with a friend? How was it?
14- What's your favorite dessert? Do you a least favorite?
23- What is your dream job? What was it as a child?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Why do I feel sleepy after massage?
Do you have a favorite? Is it ok if your partner does?
What have you learned about me that was new and/or surprising?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Are MAGA the "useful idiots" for the radical-right billionaires like Charles Koch and Elon Musk?
If you win, what will you make them do?
*** Deal Breaker Questions ***
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What ended your relationship with your best friend?
17- What’s your favorite holiday? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
51~ Are you willing to play adult games with your partner?
How do you fight the push and pull (manipulation) tactic if you want to win him?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
What was the longest? What was the shortest?
65~ Describe the best orgasm you’ve ever had? Care to share?
Why do a bra and panties have to match?
The Ice Breaker Questions
If NO, would you ever have one? Would it be with 2 men or 2 women?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
10~ How many dates are necessary before you to have sex with someone?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
17- Have you ever done drugs? Which ones? How often?
Does the thought excite you? Care to share?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
14- What is an embarrassing moment in your life? How about your most embarrassing?
9- If you could have three wishes, what would they be? Why?
I would allow you to do it… What would you do to me?
33- If you could visit any time period, when would you pick? Please explain why?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
48~ Have you ever paid or been paid for sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
11- How about if they like a certain sports team? 12-How about drinking too much?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
82~ Do you have any fantasies involving Role-Playing?
What do you dislike about me? I asked you to be 100% honest.
8- What are your thoughts on politics?
7- What are your thoughts on religion? Is there an afterlife?
30~ What's something unexpected that turns you on?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
42~ What’s your biggest regret in life?
89~ Do you like taking showers together?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
10- List 5 of your top pet peeves.
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Any that are a turn off?
*** What’s Your Favorite…? ***
2- What’s your favorite color? Do you a least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
7- What if a person smells a certain way? 8- How about smoking?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
84~ How do you feel about reading/listening to adult stories?
Do you like it when they show and tell you what they want?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
62~ Have you used adult toys?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Doctor/Nurse Stripper/Client
15- What bad habit do you wish you could quit? Do you have any addictions?
27- What was/ is nickname? Does it have a meaning behind it?
Model/Photographer Police/Criminal
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?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
21~ What was the best date you ever went on? What has been the worst?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
22- What is your favorite childhood memory? What is your least favorite?
38~ Share your most embarrassing sexual memory?
28~ What are some things that turn on? What is your biggest turn on?
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?
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…
Prisoner/Prison Guard Landlord/Tenant
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Would you read them together?
Master/Slave Boss/Maid
If yes, what?
49~ How many times have you been married? Why did they end?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
53~ How much can you tell me about the one thing you are most passionate about?
(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…)
* Give a rating for each one (0-100)
20- What’s your favorite candy? What’s your least favorite?
10- What is your favorite family tradition? What’s your least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
44~ Care to share something about yourself that no one else knows about you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
51~ What tends to bring a smile to your face?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Would you ever want to be woken up with oral and/or intercourse?
7-What do I do in bed that drives you wild? How about, what turns you off?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
13~ Is there a difference between, making love, having sex, and fucking?
26~ What side of the bed do you sleep on?
If you say it, I will stop, and we can talk about it when you are ready.
Please share Did you stop?
5~ When you first started having sex, was it what you thought it would be?
You know that I will be 100% truthful, so ask.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
61~ How willing would you be to try new sexual positions?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
8- What's your favorite flavor of ice cream? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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,
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
What would you say to prove to yourself that it was really you?
3- What’s your favorite smell? Do you a least favorite?
13- What is the craziest/scariest thing you've ever done?
52~ What are your hobbies?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Teacher/Student Stranger/One Night Stand
36~ What is your favorite time of day to have sex/make love?
Can you Deep Throat? Do you like the taste of yourself?
34- Ever been to a concert? What was your favorite? Who would you like to see?
52~ Are you willing to make “those types” of bets with your partner?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What is your favorite toy? Ever wanted to try a specific toy?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
29- How superstitious are you?
29~ What are some things that turn you off? What is your biggest turn off?
18- How often do you drink alcohol? What is your favorite drink?
Family Relation Age Play
1- What was your first impression of me? Has it changed?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
22- Do you have any birth marks? How about scars? Care to share how you got them?
3- What Superhero or Superpower would you want to be/have?
92~ Everyone needs a “safe” word. What is yours?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
48~ Do you have any siblings? Are you close to your family?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
36- Do you play video games? What is your favorite? Do you a least favorite?
39~ What are your love languages?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
*** Random Questions ***
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would /have you ever given your partner a lap dance and Striptease?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
1- What’s your favorite animal? Do you a least favorite?
Any that are a turn off?
Nothing too Serious
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
11~ Have you ever been caught by your parents or children or others while having sex?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
19- What’s your favorite fairytale? What’s your least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
3- Should Pluto still be considered a planet? 4- How about smoking?
12- What is the weirdest thing you've ever eaten?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
*** Questions about Relationships/Past ***
Do you like the “69” position? Do you prefer to be on top or bottom?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
19~ Who/when was your first “heartbreak”?
What have you learned about yourself that you did not before this?
28- What are some things that people do that irritate you?
Do you watch it? What is your favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
Escort/Client Job Applicant/Hiring Manager
50~ How many children do you have? What are their ages?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Would you mind if your partner watched it? How about together vs alone?
19- Do/have you smoked? What do you prefer? How often?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
47~ What would be your dream job and why?
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)
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
81~ Do you have any kinks and/or fetishes?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Would you allow me to clean every part of your body with my soapy hands and fingers?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
92~ Have you ever had or have an STD? How many? What was it?
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?
How well do you know me? And some of your thoughts about me
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Nurse/Patient Celebrity/Fan
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
15~ Have you ever been “in love”? Who? Care to Share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
How about if they talk dirty and/or call you names?
21- What's your favorite way to spend a weekend or time off?
9- Is there something you’ve always wanted to ask me but you’re afraid?
11- What's your favorite restaurant? What’s your least favorite?
40~ What’s the weirdest place you’ve ever had sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Over time has your thoughts on sex changed?
How old are you? Male or Female?
31- If given a chance to be immortal, would you take it? Why?
12- What’s your favorite food? What’s your least favorite?
13- How about having a certain hair cut/style?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
*** Questions About Me ***
Get this wrong and this could mean the end… :-) some funny, some not…
76~ Have you had a threesome? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
What is your view on sex? Meaning, When/Where/ How often/
4- For a pet, Cat, dog or other?
9~ How many times over your lifetime do you think you have had sex so far?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
80~ Share your top three fantasies/desires. (Be detailed) 😊
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
70~ Would/do you have/like anal sex?
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…
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How many times do you think you have “made love”?
15- What's your favorite saying? What word or phrase is your least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
That one or two things that made you go hmmmm, OMG or wow!
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
1~ How old were you when you had your first kiss? Who? Care to Share?
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?
37- Do you like your name? If you could change it, what would you change it too?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
67~ Do you like it when your partner moans and/or is vocal during sex?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Do you think this brought you closer together?