What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 13:14
9- Is there something you’ve always wanted to ask me but you’re afraid?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
19- What’s your favorite fairytale? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
31- If given a chance to be immortal, would you take it? Why?
Can you Deep Throat? Do you like the taste of yourself?
What does it mean when we dream about demons, ghosts, monsters, etc.?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
13- How about having a certain hair cut/style?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Hello I am 17 year old boy and I am interested in transgender why?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What the early "F1" movie reviews are saying ahead of New York premiere - Motorsport.com
28- What are some things that people do that irritate you?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
9- What’s your favorite season and why? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
I would allow you to do it… What would you do to me?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Why is Reddit blocked by the Indonesian government?
71~ Would you give your partner a hand or foot job? Would you receive one?
Nothing too Serious
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
What is your view on sex? Meaning, When/Where/ How often/
5- Have you ever been hypnotized? Would you allow yourself to be?
13- What’s your favorite drink? What’s your least favorite?
Has Messi scored against the Buffon?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you watch it? What is your favorite?
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Are judges being lenient on hard criminals?
11~ Have you ever been caught by your parents or children or others while having sex?
33- If you could visit any time period, when would you pick? Please explain why?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Can you tell me a depressing story?
Would you ever want to be woken up with oral and/or intercourse?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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 is the nastiest thing you had your wife do and she loved it?
Do you think this brought you closer together?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
44~ Care to share something about yourself that no one else knows about you?
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Would /have you ever given your partner a lap dance and Striptease?
92~ Have you ever had or have an STD? How many? What was it?
48~ Have you ever paid or been paid for sex?
How can you know if they are your twin flame and not limerence or obsession?
Would you mind if your partner watched it? How about together vs alone?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
21~ What was the best date you ever went on? What has been the worst?
The Ice Breaker Questions
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
54~ Would you ever go skinny dipping 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)
18~ Who/when was your first “crush”?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
83~ How do you feel about Porn?
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?
32- What's your greatest talent? Can I see it right now?
11- List at least 5 things on your bucket list. Have you done any of them already?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Will you cheat again? How can, you be sure? Define what cheating is to you.
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
40~ What’s the weirdest place you’ve ever had sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
51~ What tends to bring a smile to your face?
82~ Do you have any fantasies involving Role-Playing?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How about if they talk dirty and/or call you names?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
76~ Have you had a threesome? Care to Share?
12- What is the weirdest thing you've ever eaten?
7- What if a person smells a certain way? 8- How about smoking?
34~ Do you like the lights on or off during sex?
13- What is the craziest/scariest thing you've ever done?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
45~ How do you feel about me blindfolding you? How about blindfolding me?
13~ Is there a difference between, making love, having sex, and fucking?
9~ How many times over your lifetime do you think you have had sex so far?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
36~ What is your favorite time of day to have sex/make love?
Master/Slave Boss/Maid
1- What’s your favorite animal? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
48~ Do you have any siblings? Are you close to your family?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
*** What’s Your Favorite…? ***
29~ What are some things that turn you off? What is your biggest turn off?
2- What’s your favorite color? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
Teacher/Student Stranger/One Night Stand
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?
8- What are your thoughts on politics?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
12- What’s your favorite food? What’s your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
26~ What side of the bed do you sleep on?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
*** Questions About Me ***
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
6- Do you have dreams? Can you remember them? What do you usually dream about?
22- Do you have any birth marks? How about scars? Care to share how you got them?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
19~ Who/when was your first “heartbreak”?
14- What is an embarrassing moment in your life? How about your most embarrassing?
4- For a pet, Cat, dog or other?
25~ How do you feel about PDA? (Public Display of Affection)
17- What’s your favorite holiday? What’s your least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
20- What’s your favorite candy? What’s your least favorite?
18- How often do you drink alcohol? What is your favorite drink?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
61~ How willing would you be to try new sexual positions?
65~ Describe the best orgasm you’ve ever had? Care to share?
92~ Everyone needs a “safe” word. What is yours?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
52~ What are your hobbies?
29- How superstitious are you?
Any that are a turn off?
42~ What’s your biggest regret in life?
8- What's your favorite flavor of ice cream? Do you a least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
7- What are your thoughts on religion? Is there an afterlife?
(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’s the longest time you gone without having sex, after, having it? How much time between the others?
What was the longest? What was the shortest?
Repairman/Lonely Wife Virgin/Experienced
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
You know that I will be 100% truthful, so ask.
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,
50~ How many children do you have? What are their ages?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
*** Deal Breaker Questions ***
17- Have you ever done drugs? Which ones? How often?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
3- What’s your favorite smell? Do you a least favorite?
39~ What are your love languages?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Model/Photographer Police/Criminal
Nurse/Patient Celebrity/Fan
9- If you could have three wishes, what would they be? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
52~ Are you willing to make “those types” of bets with your partner?
Do you like the “69” position? Do you prefer to be on top or bottom?
21- What's your favorite way to spend a weekend or time off?
89~ Do you like taking showers together?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
14- What's your favorite dessert? Do you a least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Over time has your thoughts on sex changed?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
How many times do you think you have “made love”?
53~ How much can you tell me about the one thing you are most passionate about?
10- What is your favorite family tradition? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
11- How about if they like a certain sports team? 12-How about drinking too much?
If you say it, I will stop, and we can talk about it when you are ready.
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What is your favorite position? Why?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
10- List 5 of your top pet peeves.
Does the thought excite you? Care to share?
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)
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…
Family Relation Age Play
23- What is your dream job? What was it as a child?
*** Questions about Relationships/Past ***
36- Do you play video games? What is your favorite? Do you a least favorite?
Would you do it again, and would you rather 2 females or 2 males?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
10~ How many dates are necessary before you to have sex with someone?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
5~ When you first started having sex, was it what you thought it would be?
30~ What's something unexpected that turns you on?
1- What was your first impression of me? Has it changed?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Please share Did you stop?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
What do you dislike about me? I asked you to be 100% honest.
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
37- Do you like your name? If you could change it, what would you change it too?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
19- Do/have you smoked? What do you prefer? How often?
Get this wrong and this could mean the end… :-) some funny, some not…
81~ Do you have any kinks and/or fetishes?
15~ Have you ever been “in love”? Who? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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…
If yes, what?
If you win, what will you make them do?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Do you like it when they show and tell you what they want?
11- What's your favorite restaurant? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
84~ How do you feel about reading/listening to adult stories?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you read them together?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
7-What do I do in bed that drives you wild? How about, what turns you off?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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…
3- What Superhero or Superpower would you want to be/have?
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?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
62~ Have you used adult toys?
*** Random Questions ***
* Give a rating for each one (0-100)
38~ Share your most embarrassing sexual memory?
Doctor/Nurse Stripper/Client
28~ What are some things that turn on? What is your biggest turn on?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What have you learned about me that was new and/or surprising?
70~ Would/do you have/like anal sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Escort/Client Job Applicant/Hiring Manager
15- What bad habit do you wish you could quit? Do you have any addictions?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
47~ What would be your dream job and why?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
51~ Are you willing to play adult games with your partner?
60~ How important is oral sex? Do you like receiving? Do you like giving?
If YES, was it with 2 men or 2 women? Did you enjoy it?
How well do you know me? And some of your thoughts about me
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
49~ How many times have you been married? Why did they end?
33- Beach or Mountains? Or is there another place to like better?
Do you have a favorite? Is it ok if your partner does?
How old are you? Male or Female?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What have you learned about yourself that you did not before this?
Any that are a turn off?
3- Should Pluto still be considered a planet? 4- How about smoking?
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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Have you ever? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
What would you say to prove to yourself that it was really you?