What is the most interesting question you can ask to get to know someone?
Last Updated: 20.06.2025 05:05
52~ Are you willing to make “those types” of bets with your partner?
What do you dislike about me? I asked you to be 100% honest.
3- Should Pluto still be considered a planet? 4- How about smoking?
Would you date a Muslim guy? Why/why not?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Family Relation Age Play
9- Is there something you’ve always wanted to ask me but you’re afraid?
watchOS 26 Moves Latest Apple Watch Models to New Architecture - MacRumors
How many partners have you had oral sex with? 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?
36- Do you play video games? What is your favorite? Do you a least favorite?
Can you list every album you have ever listened to?
9~ How many times over your lifetime do you think you have had sex so far?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
New model helps to figure out which distant planets may host life - Space
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Nurse/Patient Celebrity/Fan
28~ What are some things that turn on? What is your biggest turn on?
What have you learned about me that was new and/or surprising?
15~ Have you ever been “in love”? Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
1- What was your first impression of me? Has it changed?
The Ice Breaker Questions
Will you cheat again? How can, you be sure? Define what cheating is to you.
Is depression a cause for always feeling tired?
70~ Would/do you have/like anal sex?
Master/Slave Boss/Maid
Can you Deep Throat? Do you like the taste of yourself?
Which brand is the best home slippers in the Middle East?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
3- What Superhero or Superpower would you want to be/have?
How did you as a human being change while growing up?
60~ How important is oral sex? Do you like receiving? Do you like giving?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
* Give a rating for each one (0-100)
Which Korean female celebrities look the best in a bikini?
Do you think this brought you closer together?
12- What’s your favorite food? What’s your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Is 1500 calories enough for a 5’3 15-year-old who is non-active?
29- How superstitious are you?
31- If given a chance to be immortal, would you take it? Why?
Would you do it again, and would you rather 2 females or 2 males?
What type of narcissist cheats more and gets pleasure out of hurting you, even if they're married?
48~ Have you ever paid or been paid for sex?
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?
42~ What’s your biggest regret in life?
What are the best mattress options for a comfortable night's sleep in Pompano Beach?
49~ How many times have you been married? Why did they end?
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)
Does the thought excite you? Care to share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
40~ What’s the weirdest place you’ve ever had sex?
92~ Everyone needs a “safe” word. What is yours?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
51~ What tends to bring a smile to your face?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Any that are a turn off?
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?
3- What’s your favorite smell? Do you a least favorite?
10~ How many dates are necessary before you to have sex with someone?
52~ What are your hobbies?
53~ How much can you tell me about the one thing you are most passionate about?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
27- What was/ is nickname? Does it have a meaning behind it?
13~ Is there a difference between, making love, having sex, and fucking?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
What is your view on sex? Meaning, When/Where/ How often/
7- What if a person smells a certain way? 8- How about smoking?
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What is your favorite toy? Ever wanted to try a specific toy?
7-What do I do in bed that drives you wild? How about, what turns you off?
21~ What was the best date you ever went on? What has been the worst?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What was the longest? What was the shortest?
1- What’s your favorite animal? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
21- What's your favorite way to spend a weekend or time off?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
That one or two things that made you go hmmmm, OMG or wow!
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
84~ How do you feel about reading/listening to adult stories?
Get this wrong and this could mean the end… :-) some funny, some not…
You know that I will be 100% truthful, so ask.
5- Have you ever been hypnotized? Would you allow yourself to be?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
89~ Do you like taking showers together?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
10- What is your favorite family tradition? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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…
19~ Who/when was your first “heartbreak”?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
Would you ever want to be woken up with oral and/or intercourse?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Escort/Client Job Applicant/Hiring Manager
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
14- What is an embarrassing moment in your life? How about your most embarrassing?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
11- What's your favorite restaurant? What’s your least favorite?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
17- What’s your favorite holiday? What’s your least favorite?
4- For a pet, Cat, dog or other?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
38~ Share your most embarrassing sexual memory?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you watch it? What is your favorite?
What would you say to prove to yourself that it was really you?
Nothing too Serious
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
*** Random Questions ***
61~ How willing would you be to try new sexual positions?
8- What's your favorite flavor of ice cream? Do you a least favorite?
9- If you could have three wishes, what would they be? Why?
If you win, what will you make them do?
What is your favorite position? Why?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
47~ What would be your dream job and why?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
23- What is your dream job? What was it as a child?
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?
10- List 5 of your top pet peeves.
65~ Describe the best orgasm you’ve ever had? 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…
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
*** Questions About Me ***
12- What is the weirdest thing you've ever eaten?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
17- Have you ever done drugs? Which ones? How often?
11- List at least 5 things on your bucket list. Have you done any of them already?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
25~ How do you feel about PDA? (Public Display of Affection)
Do you like it when they show and tell you what they want?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What have you learned about yourself that you did not before this?
Over time has your thoughts on sex changed?
81~ Do you have any kinks and/or fetishes?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
67~ Do you like it when your partner moans and/or is vocal during sex?
13- What’s your favorite drink? What’s your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
19- Do/have you smoked? What do you prefer? How often?
51~ Are you willing to play adult games with your partner?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
22- What is your favorite childhood memory? What is your least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you have a favorite? Is it ok if your partner does?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
28- What are some things that people do that irritate you?
If you say it, I will stop, and we can talk about it when you are ready.
How many times do you think you have “made love”?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
1~ How old were you when you had your first kiss? Who? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Have you ever? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
I would allow you to do it… What would you do to me?
Prisoner/Prison Guard Landlord/Tenant
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
33- If you could visit any time period, when would you pick? Please explain why?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Repairman/Lonely Wife Virgin/Experienced
*** Deal Breaker Questions ***
Would /have you ever given your partner a lap dance and Striptease?
Teacher/Student Stranger/One Night Stand
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How well do you know me? And some of your thoughts about me
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Please share Did you stop?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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,
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Any that are a turn off?
36~ What is your favorite time of day to have sex/make love?
83~ How do you feel about Porn?
Would you read them together?
*** Questions about Relationships/Past ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
33- Beach or Mountains? Or is there another place to like better?
32- What's your greatest talent? Can I see it right now?
18~ Who/when was your first “crush”?
19- What’s your favorite fairytale? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If yes, what?
13- What is the craziest/scariest thing you've ever done?
30~ What's something unexpected that turns you on?
5~ When you first started having sex, was it what you thought it would be?
How old are you? Male or Female?
11- How about if they like a certain sports team? 12-How about drinking too much?
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?
Would you mind if your partner watched it? How about together vs alone?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
18- How often do you drink alcohol? What is your favorite drink?
Model/Photographer Police/Criminal
50~ How many children do you have? What are their ages?
20- What’s your favorite candy? What’s your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
13- How about having a certain hair cut/style?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
How about if they talk dirty and/or call you names?
*** What’s Your Favorite…? ***
7- What are your thoughts on religion? Is there an afterlife?
2- What’s your favorite color? Do you a least favorite?
29~ What are some things that turn you off? What is your biggest turn off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
92~ Have you ever had or have an STD? How many? What was it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
39~ What are your love languages?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
62~ Have you used adult toys?
71~ Would you give your partner a hand or foot job? Would you receive one?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
34~ Do you like the lights on or off during sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
34- Ever been to a concert? What was your favorite? Who would you like to see?
76~ Have you had a threesome? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
8- What are your thoughts on politics?
15- What's your favorite saying? What word or phrase is your least favorite?
48~ Do you have any siblings? Are you close to your family?
9- What’s your favorite season and why? What’s your least favorite?
82~ Do you have any fantasies involving Role-Playing?
(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…)
Doctor/Nurse Stripper/Client
Would you allow me to clean every part of your body with my soapy hands and fingers?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)