What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 04:56
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
71~ Would you give your partner a hand or foot job? Would you receive one?
Why did Obito, a supposed "bad person," do good things for Kakashi?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Repairman/Lonely Wife Virgin/Experienced
34~ Do you like the lights on or off during sex?
5~ When you first started having sex, was it what you thought it would be?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
82~ Do you have any fantasies involving Role-Playing?
18~ Who/when was your first “crush”?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Have you ever? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
What is your analysis of Walter White from Breaking Bad?
50~ How many children do you have? What are their ages?
1~ How old were you when you had your first kiss? Who? Care to Share?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How do you get started in bestiality with a dog as a male?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
67~ Do you like it when your partner moans and/or is vocal during sex?
Why would my husband cheat on me with an ugly fat woman?
81~ Do you have any kinks and/or fetishes?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Family Relation Age Play
92~ Everyone needs a “safe” word. What is yours?
Please share Did you stop?
A recipe to reverse cancer’s sweet tooth - Cold Spring Harbor Laboratory
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
3- What’s your favorite smell? Do you a least favorite?
51~ Are you willing to play adult games with your partner?
10~ How many dates are necessary before you to have sex with someone?
31- If given a chance to be immortal, would you take it? Why?
37- Do you like your name? If you could change it, what would you change it too?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
If you win, what will you make them do?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What are the best self-care practices to improve mental health?
7- What are your thoughts on religion? Is there an afterlife?
21- What's your favorite way to spend a weekend or time off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What is your secret to glowing skin?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
You know that I will be 100% truthful, so ask.
* Give a rating for each one (0-100)
What have you learned about yourself that you did not before this?
52~ Are you willing to make “those types” of bets with your partner?
Get this wrong and this could mean the end… :-) some funny, some not…
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
9- If you could have three wishes, what would they be? Why?
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,
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Master/Slave Boss/Maid
3- Should Pluto still be considered a planet? 4- How about smoking?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
11- What's your favorite restaurant? What’s your least favorite?
Escort/Client Job Applicant/Hiring Manager
Do you think this brought you closer together?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Would you read them together?
9- What’s your favorite season and why? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
89~ Do you like taking showers together?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
How well do you know me? And some of your thoughts about me
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
42~ What’s your biggest regret in life?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Do you watch it? What is your favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Does the thought excite you? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
19- What’s your favorite fairytale? What’s your least favorite?
The Ice Breaker Questions
How about if they talk dirty and/or call you names?
30~ What's something unexpected that turns you on?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
54~ Would you ever go skinny dipping 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?
(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…)
80~ Share your top three fantasies/desires. (Be detailed) 😊
5- Have you ever been hypnotized? Would you allow yourself to be?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do you have a favorite? Is it ok if your partner does?
Any that are a turn off?
36~ What is your favorite time of day to have sex/make love?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
48~ Do you have any siblings? Are you close to your family?
Any that are a turn off?
10- List 5 of your top pet peeves.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
29~ What are some things that turn you off? What is your biggest turn off?
12- What is the weirdest thing you've ever eaten?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Would you allow me to clean every part of your body with my soapy hands and fingers?
If YES, was it with 2 men or 2 women? Did you enjoy it?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Nothing too Serious
What’s the longest time you gone without having sex, after, having it? How much time between the others?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
If yes, what?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Can you Deep Throat? Do you like the taste of yourself?
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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
11- How about if they like a certain sports team? 12-How about drinking too much?
Over time has your thoughts on sex changed?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
65~ Describe the best orgasm you’ve ever had? Care to share?
Model/Photographer Police/Criminal
24~ What are your expectations in a relationship? (I know a very big question, take your time)
15- What bad habit do you wish you could quit? Do you have any addictions?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
19~ Who/when was your first “heartbreak”?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
*** What’s Your Favorite…? ***
60~ How important is oral sex? Do you like receiving? Do you like giving?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Nurse/Patient Celebrity/Fan
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?
62~ Have you used adult toys?
8- What are your thoughts on politics?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
28~ What are some things that turn on? What is your biggest turn on?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
44~ Care to share something about yourself that no one else knows about you?
22- What is your favorite childhood memory? What is your least favorite?
13- What’s your favorite drink? 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…
46~ Have you ever used furniture, or other types of things to aid you while having sex?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
17- What’s your favorite holiday? What’s your least favorite?
17- Have you ever done drugs? Which ones? How often?
47~ What would be your dream job and why?
If NO, would you ever have one? Would it be with 2 men or 2 women?
61~ How willing would you be to try new sexual positions?
52~ What are your hobbies?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
76~ Have you had a threesome? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What is your favorite toy? Ever wanted to try a specific toy?
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?
What is your favorite position? Why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
51~ What tends to bring a smile to your face?
Would you mind if your partner watched it? How about together vs alone?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Will you cheat again? How can, you be sure? Define what cheating is to you.
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
32- What's your greatest talent? Can I see it right now?
33- Beach or Mountains? Or is there another place to like better?
1- What was your first impression of me? Has it changed?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What is your view on sex? Meaning, When/Where/ How often/
25~ How do you feel about PDA? (Public Display of Affection)
38~ Share your most embarrassing sexual memory?
Teacher/Student Stranger/One Night Stand
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
11- List at least 5 things on your bucket list. Have you done any of them already?
*** Questions about Relationships/Past ***
41~ Are there moments in your past that you would want to change? Please share 3 of them.
26~ What side of the bed do you sleep on?
How many times do you think you have “made love”?
92~ Have you ever had or have an STD? How many? What was it?
7-What do I do in bed that drives you wild? How about, what turns you off?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
23- What is your dream job? What was it as a child?
If you say it, I will stop, and we can talk about it when you are ready.
36- Do you play video games? What is your favorite? Do you a least favorite?
How old are you? Male or Female?
4- For a pet, Cat, dog or other?
20- What’s your favorite candy? What’s your least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
13- How about having a certain hair cut/style?
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?
*** Questions About Me ***
Do you like the “69” position? Do you prefer to be on top or bottom?
2- What’s your favorite color? Do you a least favorite?
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?
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?
28- What are some things that people do that irritate you?
33- If you could visit any time period, when would you pick? Please explain why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
11~ Have you ever been caught by your parents or children or others while having sex?
13- What is the craziest/scariest thing you've ever done?
49~ How many times have you been married? Why did they end?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
Doctor/Nurse Stripper/Client
*** Random Questions ***
12- What’s your favorite food? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
21~ What was the best date you ever went on? What has been the worst?
15- What's your favorite saying? What word or phrase is your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
9~ How many times over your lifetime do you think you have had sex so far?
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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Would you ever want to be woken up with oral and/or intercourse?
83~ How do you feel about Porn?
Would you do it again, and would you rather 2 females or 2 males?
15~ Have you ever been “in love”? Who? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
How many partners have you had oral sex with? Who? Care to Share?
27- What was/ is nickname? Does it have a meaning behind it?
70~ Would/do you have/like anal sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Prisoner/Prison Guard Landlord/Tenant
8- What's your favorite flavor of ice cream? Do you a least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
What was the longest? What was the shortest?
13~ Is there a difference between, making love, having sex, and fucking?
What would you say to prove to yourself that it was really you?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
39~ What are your love languages?
40~ What’s the weirdest place you’ve ever had sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
19- Do/have you smoked? What do you prefer? How often?
29- How superstitious are you?
What have you learned about me that was new and/or surprising?
*** Deal Breaker Questions ***
18- How often do you drink alcohol? What is your favorite drink?
9- Is there something you’ve always wanted to ask me but you’re afraid?
18- What’s your favorite way to relax after a long day? What’s your 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…
I would allow you to do it… What would you do to me?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you like it when they show and tell you what they want?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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)
That one or two things that made you go hmmmm, OMG or wow!
What do you dislike about me? I asked you to be 100% honest.
48~ Have you ever paid or been paid for sex?
7- What if a person smells a certain way? 8- How about smoking?