What is the most interesting question you can ask to get to know someone?
Last Updated: 24.06.2025 00:10
Escort/Client Job Applicant/Hiring Manager
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
Have you ever had sex with your female cousin? How did it start?
11- List at least 5 things on your bucket list. Have you done any of them already?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
45~ How do you feel about me blindfolding you? How about blindfolding me?
Xbox Building A Handheld 'Makes No Sense', Says Former Blizzard Boss - Pure Xbox
17- Have you ever done drugs? Which ones? How often?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
1~ How old were you when you had your first kiss? Who? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
Would you mind if your partner watched it? How about together vs alone?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Qantas to close low-cost arm Jetstar Asia - CNN
33- If you could visit any time period, when would you pick? Please explain why?
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?
37- Do you like your name? If you could change it, what would you change it too?
18- How often do you drink alcohol? What is your favorite drink?
Does the thought excite you? Care to share?
Is it helpful to justify the reason for a breakup when ending a relationship?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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,
49~ If you could, would you want to be the opposite sex for a day, week, or year?
13- How about having a certain hair cut/style?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Having Low Levels Of This Vitamin Can Cause Dry Eyes. Are You Getting Enough? - Women's Health
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)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Please share Did you stop?
Secret Characters in Elden Ring Nightreign: How to Unlock the Revenant and Duchess - CNET
Over time has your thoughts on sex changed?
9- If you could have three wishes, what would they be? Why?
15- What bad habit do you wish you could quit? Do you have any addictions?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
83~ How do you feel about Porn?
Amazon planning $10B investment in North Carolina for data center and AI campus - AP News
10- What is your favorite family tradition? What’s your least favorite?
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…
Would /have you ever given your partner a lap dance and Striptease?
Netflix’s Buzzy New Doc About an Infamous Tragedy Shows It’s Just the Beginning - Slate Magazine
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
39~ What are your love languages?
Dakota Johnson Is “Always Psyched” To Film Sex Scenes - The Cut
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What do you dislike about me? I asked you to be 100% honest.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
82~ Do you have any fantasies involving Role-Playing?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Teacher/Student Stranger/One Night Stand
33- Beach or Mountains? Or is there another place to like better?
Family Relation Age Play
8- What's your favorite flavor of ice cream? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
67~ Do you like it when your partner moans and/or is vocal during sex?
Get this wrong and this could mean the end… :-) some funny, some not…
2- What’s your favorite color? Do you a least favorite?
51~ What tends to bring a smile to your face?
Nothing too Serious
19- What’s your favorite fairytale? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
If you win, what will you make them do?
92~ Have you ever had or have an STD? How many? What was it?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Any that are a turn off?
40~ What’s the weirdest place you’ve ever had sex?
Can you Deep Throat? Do you like the taste of yourself?
What is your favorite toy? Ever wanted to try a specific toy?
34~ Do you like the lights on or off during sex?
3- What Superhero or Superpower would you want to be/have?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
27- What was/ is nickname? Does it have a meaning behind it?
30~ What's something unexpected that turns you on?
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?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
Would you ever want to be woken up with oral and/or intercourse?
6- Do you have dreams? Can you remember them? What do you usually dream about?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
89~ Do you like taking showers together?
92~ Everyone needs a “safe” word. What is yours?
* Give a rating for each one (0-100)
17- What’s your favorite holiday? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
How old are you? Male or Female?
22- What is your favorite childhood memory? What is your least favorite?
21- What's your favorite way to spend a weekend or time off?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you watch it? What is your favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
52~ What are your hobbies?
12- What’s your favorite food? What’s your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
7-What do I do in bed that drives you wild? How about, what turns you off?
How well do you know me? And some of your thoughts about me
76~ Have you had a threesome? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
36- Do you play video games? What is your favorite? Do you a least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
25~ How do you feel about PDA? (Public Display of Affection)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
10~ How many dates are necessary before you to have sex with someone?
65~ Describe the best orgasm you’ve ever had? Care to share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Do you think this brought you closer together?
50~ How many children do you have? What are their ages?
That one or two things that made you go hmmmm, OMG or wow!
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
29- How superstitious are you?
19- Do/have you smoked? What do you prefer? How often?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
3- What’s your favorite smell? Do you a least favorite?
Doctor/Nurse Stripper/Client
14- What's your favorite dessert? Do you a least favorite?
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…
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
4- For a pet, Cat, dog or other?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
What have you learned about me that was new and/or surprising?
If you say it, I will stop, and we can talk about it when you are ready.
Do you like the “69” position? Do you prefer to be on top or bottom?
11- What's your favorite restaurant? What’s your least favorite?
The Ice Breaker Questions
1- What’s your favorite animal? Do you a least favorite?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
31- If given a chance to be immortal, would you take it? Why?
What is your view on sex? Meaning, When/Where/ How often/
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
*** Questions About Me ***
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Nurse/Patient Celebrity/Fan
23- What is your dream job? What was it as a child?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
7- What if a person smells a certain way? 8- How about smoking?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
You know that I will be 100% truthful, so ask.
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
*** Deal Breaker Questions ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
*** Random Questions ***
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
*** What’s Your Favorite…? ***
(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…)
29~ What are some things that turn you off? What is your biggest turn off?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
18~ Who/when was your first “crush”?
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 read them together?
28~ What are some things that turn on? What is your biggest turn on?
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
If yes, what?
What would you say to prove to yourself that it was really you?
What is your favorite position? Why?
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?
12- What is the weirdest thing you've ever eaten?
11- How about if they like a certain sports team? 12-How about drinking too much?
How many times do you think you have “made love”?
Master/Slave Boss/Maid
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
5~ When you first started having sex, was it what you thought it would be?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
3- Should Pluto still be considered a planet? 4- How about smoking?
42~ What’s your biggest regret in life?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
36~ What is your favorite time of day to have sex/make love?
49~ How many times have you been married? Why did they end?
15~ Have you ever been “in love”? Who? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
61~ How willing would you be to try new sexual positions?
Do you have a favorite? Is it ok if your partner does?
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?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
53~ How much can you tell me about the one thing you are most passionate about?
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?
13- What is the craziest/scariest thing you've ever done?
Any that are a turn off?
19~ Who/when was your first “heartbreak”?
I would allow you to do it… What would you do to me?
21~ What was the best date you ever went on? What has been the worst?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Have you ever? Care to Share?
Model/Photographer Police/Criminal
70~ Would/do you have/like anal sex?
1- What was your first impression of me? Has it changed?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
48~ Have you ever paid or been paid for sex?
Do you like it when they show and tell you what they want?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
8- What are your thoughts on politics?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
51~ Are you willing to play adult games with your partner?
How about if they talk dirty and/or call you names?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
*** Questions about Relationships/Past ***
47~ What would be your dream job and why?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
How many partners have you had oral sex with? Who? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
28- What are some things that people do that irritate you?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
20- What’s your favorite candy? What’s your least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
7- What are your thoughts on religion? Is there an afterlife?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Repairman/Lonely Wife Virgin/Experienced
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
What have you learned about yourself that you did not before this?
13~ Is there a difference between, making love, having sex, and fucking?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
81~ Do you have any kinks and/or fetishes?
38~ Share your most embarrassing sexual memory?
26~ What side of the bed do you sleep on?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Would you do it again, and would you rather 2 females or 2 males?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
84~ How do you feel about reading/listening to adult stories?
22- Do you have any birth marks? How about scars? Care to share how you got them?
13- What’s your favorite drink? What’s your least favorite?