What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 02:11
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
23- What is your dream job? What was it as a child?
What are the psychological reasons behind an extreme obsession with another human being?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
What is your view on sex? Meaning, When/Where/ How often/
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How can fashion design be used to make a political statement in popular culture, and society?
36- Do you play video games? What is your favorite? Do you a least favorite?
84~ How do you feel about reading/listening to adult stories?
5~ When you first started having sex, was it what you thought it would be?
Bats don't get cancer, now scientists think they know the reason - Earth.com
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What was the longest? What was the shortest?
*** Deal Breaker Questions ***
What is the hidden meaning behind 'Skibidi Ohio', and why is it trending?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
*** Random Questions ***
53~ How much can you tell me about the one thing you are most passionate about?
10- List 5 of your top pet peeves.
Is it true that all men want a woman who looks like an Instagram “model”?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
83~ How do you feel about Porn?
44~ Care to share something about yourself that no one else knows about you?
As a woman, what would be you response to a male friend’s offer of a full body massage?
89~ Do you like taking showers together?
34~ Do you like the lights on or off during sex?
82~ Do you have any fantasies involving Role-Playing?
Get this wrong and this could mean the end… :-) some funny, some not…
24~ What are your expectations in a relationship? (I know a very big question, take your time)
17- What’s your favorite holiday? What’s your least favorite?
When gallery photos are deleted at the same time, why are Google photos also deleted?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
26~ What side of the bed do you sleep on?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
19- Do/have you smoked? What do you prefer? How often?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
When does a man tell a woman he has feelings for her?
60~ How important is oral sex? Do you like receiving? Do you like giving?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
12- What’s your favorite food? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
My son is possessed, now he has psychosis. Can someone help me?
Does the thought excite you? Care to share?
13~ Is there a difference between, making love, having sex, and fucking?
Escort/Client Job Applicant/Hiring Manager
Any that are a turn off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
18~ Who/when was your first “crush”?
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- 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?
7- What if a person smells a certain way? 8- How about smoking?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- Should Pluto still be considered a planet? 4- How about smoking?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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,
Model/Photographer Police/Criminal
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you like the “69” position? Do you prefer to be on top or bottom?
What do you dislike about me? I asked you to be 100% honest.
22- Do you have any birth marks? How about scars? Care to share how you got them?
61~ How willing would you be to try new sexual positions?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
1~ How old were you when you had your first kiss? Who? Care to Share?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? 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…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Have you ever? Care to Share?
How well do you know me? And some of your thoughts about me
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
12- What is the weirdest thing you've ever eaten?
Nurse/Patient Celebrity/Fan
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
37- Do you like your name? If you could change it, what would you change it too?
8- What are your thoughts on politics?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Any that are a turn off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Do you watch it? What is your favorite?
70~ Would/do you have/like anal sex?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
*** Questions about Relationships/Past ***
48~ Have you ever paid or been paid for sex?
Do you like it when they show and tell you what they want?
32- What's your greatest talent? Can I see it right now?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
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?
Do you have a favorite? Is it ok if your partner does?
Would you do it again, and would you rather 2 females or 2 males?
76~ Have you had a threesome? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
*** Questions About Me ***
29~ What are some things that turn you off? What is your biggest turn off?
28- What are some things that people do that irritate you?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
9- What’s your favorite season and why? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
71~ Would you give your partner a hand or foot job? Would you receive one?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
13- What’s your favorite drink? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Would /have you ever given your partner a lap dance and Striptease?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
52~ What are your hobbies?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
15- What bad habit do you wish you could quit? Do you have any addictions?
Please share Did you stop?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
Can you Deep Throat? Do you like the taste of yourself?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
The Ice Breaker Questions
Nothing too Serious
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
11- List at least 5 things on your bucket list. Have you done any of them already?
35- Do you like playing board or cards game? 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.
50~ How many children do you have? What are their ages?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
I would allow you to do it… What would you do to me?
49~ How many times have you been married? Why did they end?
36~ What is your favorite time of day to have sex/make love?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
28~ What are some things that turn on? What is your biggest turn on?
How about if they talk dirty and/or call you names?
51~ What tends to bring a smile to your face?
80~ Share your top three fantasies/desires. (Be detailed) 😊
3- What Superhero or Superpower would you want to be/have?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What have you learned about yourself that you did not before this?
29- How superstitious are you?
What have you learned about me that was new and/or surprising?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
81~ Do you have any kinks and/or fetishes?
11~ Have you ever been caught by your parents or children or others while having sex?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
How old are you? Male or Female?
If yes, what?
21- What's your favorite way to spend a weekend or time off?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
51~ Are you willing to play adult games with your partner?
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?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What would you say to prove to yourself that it was really 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?
40~ What’s the weirdest place you’ve ever had sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
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?
What is your favorite position? Why?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
What is your favorite toy? Ever wanted to try a specific toy?
20- What’s your favorite candy? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? 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?
Doctor/Nurse Stripper/Client
Do you think this brought you closer together?
52~ Are you willing to make “those types” of bets with your partner?
Would you ever want to be woken up with oral and/or intercourse?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
30~ What's something unexpected that turns you on?
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?
9- If you could have three wishes, what would they be? Why?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
21~ What was the best date you ever went on? What has been the worst?
11- What's your favorite restaurant? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
19- What’s your favorite fairytale? What’s your least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
If NO, would you ever have one? Would it be with 2 men or 2 women?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
13- How about having a certain hair cut/style?
10~ How many dates are necessary before you to have sex with someone?
Prisoner/Prison Guard Landlord/Tenant
92~ Everyone needs a “safe” word. What is yours?
38~ Share your most embarrassing sexual memory?
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~ How old were you when you got to 2nd base? (Tongue kissing, breast feeling, or outside the clothes genital contact) Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
27- What was/ is nickname? Does it have a meaning behind it?
You know that I will be 100% truthful, so ask.
Teacher/Student Stranger/One Night Stand
19~ Who/when was your first “heartbreak”?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1- What was your first impression of me? Has it changed?
Repairman/Lonely Wife Virgin/Experienced
7-What do I do in bed that drives you wild? How about, what turns you off?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
8- What's your favorite flavor of ice cream? Do you a least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
42~ What’s your biggest regret in life?
7- What are your thoughts on religion? Is there an afterlife?
10- What is your favorite family tradition? What’s your least favorite?
62~ Have you used adult toys?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
31- If given a chance to be immortal, would you take it? Why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
* Give a rating for each one (0-100)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would you mind if your partner watched it? How about together vs alone?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
3- What’s your favorite smell? Do you a least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
2- What’s your favorite color? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
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…
How many times do you think you have “made love”?
25~ How do you feel about PDA? (Public Display of Affection)
18- How often do you drink alcohol? What is your favorite drink?
Master/Slave Boss/Maid
How many partners have you had oral sex with? Who? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
1- What’s your favorite animal? Do you a least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
15- What's your favorite saying? What word or phrase is your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Over time has your thoughts on sex changed?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
14- What's your favorite dessert? Do you a least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
47~ What would be your dream job and why?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Family Relation Age Play
92~ Have you ever had or have an STD? How many? What was it?
33- Beach or Mountains? Or is there another place to like better?
9- Is there something you’ve always wanted to ask me but you’re afraid?
17- Have you ever done drugs? Which ones? How often?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
If you win, what will you make them do?
(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…)
13- What is the craziest/scariest thing you've ever done?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
*** What’s Your Favorite…? ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you read them together?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
39~ What are your love languages?
48~ Do you have any siblings? Are you close to your family?
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
That one or two things that made you go hmmmm, OMG or wow!
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?