What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 22:08

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