What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 03:33
92~ Have you ever had or have an STD? How many? What was it?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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?
What's the most valuable lesson you've learned in life, and how has it impacted your journey so far?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Model/Photographer Police/Criminal
What is your view on sex? Meaning, When/Where/ How often/
Google Play Store replaces ‘1-tap buy’ with ‘Slide to buy’ - 9to5Google
Do you like it when they show and tell you what they want?
How many partners have you had oral sex with? Who? Care to Share?
48~ Do you have any siblings? Are you close to your family?
How do you help patients stop hearing voices?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Do you watch it? What is your favorite?
22- What is your favorite childhood memory? What is your least favorite?
Microsoft's OpenAI partnership is fraying at the seams - Axios
51~ What tends to bring a smile to your face?
38~ Share your most embarrassing sexual memory?
3- What’s your favorite smell? Do you a least favorite?
Can I use the LEG PRESS to build muscle?
What do you dislike about me? I asked you to be 100% honest.
20- What’s your favorite candy? What’s your least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
How can I remove decimals in math?
That one or two things that made you go hmmmm, OMG or wow!
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Does the thought excite you? Care to share?
What are the best items to buy from a furniture shop?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
If yes, what?
8- What are your thoughts on politics?
67~ Do you like it when your partner moans and/or is vocal during sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Doctor/Nurse Stripper/Client
Why do guys have better skin than women even though women use more product?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If YES, was it with 2 men or 2 women? Did you enjoy it?
21- What's your favorite way to spend a weekend or time off?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13~ Is there a difference between, making love, having sex, and fucking?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
* Give a rating for each one (0-100)
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…
52~ Are you willing to make “those types” of bets with your partner?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
53~ How much can you tell me about the one thing you are most passionate about?
13- How about having a certain hair cut/style?
37- Do you like your name? If you could change it, what would you change it too?
Will you cheat again? How can, you be sure? Define what cheating is to you.
26~ What side of the bed do you sleep on?
5~ When you first started having sex, was it what you thought it would be?
Prisoner/Prison Guard Landlord/Tenant
Would /have you ever given your partner a lap dance and Striptease?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
24~ What are your expectations in a relationship? (I know a very big question, take your time)
61~ How willing would you be to try new sexual positions?
If you win, what will you make them do?
70~ Would/do you have/like anal sex?
Would you read them together?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
3- Should Pluto still be considered a planet? 4- How about smoking?
34- Ever been to a concert? What was your favorite? Who would you like to see?
19~ Who/when was your first “heartbreak”?
32- What's your greatest talent? Can I see it right now?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
48~ Have you ever paid or been paid for sex?
Would you ever want to be woken up with oral and/or intercourse?
1- What was your first impression of me? Has it changed?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Have you ever? Care to Share?
Do you have a favorite? Is it ok if your partner does?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
2- What’s your favorite color? Do you a least favorite?
23- What is your dream job? What was it as a child?
29- How superstitious are you?
27- What was/ is nickname? Does it have a meaning behind it?
44~ Care to share something about yourself that no one else knows about you?
Do you think this brought you closer together?
82~ Do you have any fantasies involving Role-Playing?
42~ What’s your biggest regret in life?
30~ What's something unexpected that turns you on?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Master/Slave Boss/Maid
36- Do you play video games? What is your favorite? Do you a least favorite?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Teacher/Student Stranger/One Night Stand
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Any that are a turn off?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Can you Deep Throat? Do you like the taste of yourself?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
10- List 5 of your top pet peeves.
6- Do you have dreams? Can you remember them? What do you usually dream about?
11~ Have you ever been caught by your parents or children or others while having sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Family Relation Age Play
18- How often do you drink alcohol? What is your favorite drink?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
31- If given a chance to be immortal, would you take it? Why?
7- What are your thoughts on religion? Is there an afterlife?
What was the longest? What was the shortest?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
40~ What’s the weirdest place you’ve ever had sex?
9~ How many times over your lifetime do you think you have had sex so far?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Any that are a turn off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Nurse/Patient Celebrity/Fan
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
3- What Superhero or Superpower would you want to be/have?
What is your favorite toy? Ever wanted to try a specific toy?
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)
15- What bad habit do you wish you could quit? Do you have any addictions?
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?
62~ Have you used adult toys?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Escort/Client Job Applicant/Hiring Manager
Nothing too Serious
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?
76~ Have you had a threesome? Care to Share?
47~ What would be your dream job and why?
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
19- What’s your favorite fairytale? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
28- What are some things that people do that irritate you?
19- Do/have you smoked? What do you prefer? How often?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
12- What’s your favorite food? What’s your least favorite?
Over time has your thoughts on sex changed?
4- For a pet, Cat, dog or other?
13- What is the craziest/scariest thing you've ever done?
The Ice Breaker Questions
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
49~ How many times have you been married? Why did they end?
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,
How well do you know me? And some of your thoughts about me
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
29~ What are some things that turn you off? What is your biggest turn off?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
*** Deal Breaker Questions ***
9- If you could have three wishes, what would they be? Why?
11- How about if they like a certain sports team? 12-How about drinking too much?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
83~ How do you feel about Porn?
*** Random Questions ***
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
25~ How do you feel about PDA? (Public Display of Affection)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
10- What is your favorite family tradition? What’s your least favorite?
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?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
8- What's your favorite flavor of ice cream? Do you a least favorite?
How old are you? Male or Female?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What would you say to prove to yourself that it was really you?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
11- List at least 5 things on your bucket list. Have you done any of them already?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Would you do it again, and would you rather 2 females or 2 males?
How many times do you think you have “made love”?
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?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What have you learned about me that was new and/or surprising?
22- Do you have any birth marks? How about scars? Care to share how you got them?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
50~ How many children do you have? What are their ages?
What have you learned about yourself that you did not before this?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
What is your favorite position? Why?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
10~ How many dates are necessary before you to have sex with someone?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
34~ Do you like the lights on or off during sex?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you allow me to clean every part of your body with my soapy hands and fingers?
15- What's your favorite saying? What word or phrase is your least favorite?
*** Questions About Me ***
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Would you mind if your partner watched it? How about together vs alone?
60~ How important is oral sex? Do you like receiving? Do you like giving?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
1- What’s your favorite animal? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
If NO, would you ever have one? Would it be with 2 men or 2 women?
* Which of the following turns you on the most? Do you have any not on this list? 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…
33- Beach or Mountains? Or is there another place to like better?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
89~ Do you like taking showers together?
*** What’s Your Favorite…? ***
51~ Are you willing to play adult games with your partner?
65~ Describe the best orgasm you’ve ever had? Care to share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
12- What is the weirdest thing you've ever eaten?
13- What’s your favorite drink? What’s your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
You know that I will be 100% truthful, so ask.
7- What if a person smells a certain way? 8- 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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
45~ How do you feel about me blindfolding you? How about blindfolding me?
18~ Who/when was your first “crush”?
9- What’s your favorite season and why? What’s your least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
17- What’s your favorite holiday? What’s your least favorite?
How about if they talk dirty and/or call you names?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
39~ What are your love languages?
(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…)
5- Have you ever been hypnotized? Would you allow yourself to be?
Repairman/Lonely Wife Virgin/Experienced
7-What do I do in bed that drives you wild? How about, what turns you off?
Get this wrong and this could mean the end… :-) some funny, some not…
Please share Did you stop?
92~ Everyone needs a “safe” word. What is yours?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
81~ Do you have any kinks and/or fetishes?
52~ What are your hobbies?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
17- Have you ever done drugs? Which ones? How often?
11- What's your favorite restaurant? What’s your least favorite?
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
15~ Have you ever been “in love”? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
36~ What is your favorite time of day to have sex/make love?
*** Questions about Relationships/Past ***
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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?
If you say it, I will stop, and we can talk about it when you are ready.