What is the most interesting question you can ask to get to know someone?
Last Updated: 30.06.2025 08:05
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
9- What’s your favorite season and why? What’s your least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Get this wrong and this could mean the end… :-) some funny, some not…
Federal judge clears way for NYC broker fee ban to begin - Gothamist
What is your favorite toy? Ever wanted to try a specific toy?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Would /have you ever given your partner a lap dance and Striptease?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Teacher/Student Stranger/One Night Stand
What was the longest? What was the shortest?
It is possible to remove a voice from a double voice audio so I can hear just the one voice?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Does eating mushrooms cause skin breakouts?
17- What’s your favorite holiday? What’s your least favorite?
*** Questions about Relationships/Past ***
15- What's your favorite saying? What word or phrase is your least favorite?
What are some reasons why people may fear strong men?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
8- What are your thoughts on politics?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you think your landlord should have a key to your room?
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?
Have you ever? Care to Share?
RFK Jr. purges every vaccine adviser on CDC panel; will pick replacements - The Washington Post
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)
7- What if a person smells a certain way? 8- How about smoking?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Cosmic Mystery Solved: Astronomers Have Discovered the Universe’s “Missing” Matter - SciTechDaily
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
14- What's your favorite dessert? Do you a least favorite?
*** Questions About Me ***
What's wrong with white women?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Any that are a turn off?
What are some interests in sharing pictures of wives?
How many times do you think you have “made love”?
13- How about having a certain hair cut/style?
18- How often do you drink alcohol? What is your favorite drink?
'Alligator Alcatraz': Florida building migrant detention centre in Everglades - BBC
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
48~ Have you ever paid or been paid for sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
What’s the worst thing you caught anyone in your family doing?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Scientists Just Connected These Foods with an 80% Lower Risk of Cognitive Decline - EatingWell
Can you Deep Throat? Do you like the taste of yourself?
Would you do it again, and would you rather 2 females or 2 males?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Stellar Blade More Than Doubles Sony’s Previous Steam CCU Record for Single Player Games - Wccftech
62~ Have you used adult toys?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
*** Deal Breaker Questions ***
3- What Superhero or Superpower would you want to be/have?
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?
17- Have you ever done drugs? Which ones? How often?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
26~ What side of the bed do you sleep on?
47~ What would be your dream job and why?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
33- Beach or Mountains? Or is there another place to like better?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Would you read them together?
15- What bad habit do you wish you could quit? Do you have any addictions?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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)
How well do you know me? And some of your thoughts about me
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
* Give a rating for each one (0-100)
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Escort/Client Job Applicant/Hiring Manager
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
If you say it, I will stop, and we can talk about it when you are ready.
28- What are some things that people do that irritate you?
30~ What's something unexpected that turns you on?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
The Ice Breaker Questions
If yes, what?
7-What do I do in bed that drives you wild? How about, what turns you off?
5~ When you first started having sex, was it what you thought it would be?
Do you like it when they show and tell you what they want?
Master/Slave Boss/Maid
25~ How do you feel about PDA? (Public Display of Affection)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
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 ever want to be woken up with oral and/or intercourse?
28~ What are some things that turn on? What is your biggest turn on?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
6- Do you have dreams? Can you remember them? What do you usually dream about?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
37- Do you like your name? If you could change it, what would you change it too?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
29~ What are some things that turn you off? What is your biggest turn off?
That one or two things that made you go hmmmm, OMG or wow!
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
11- List at least 5 things on your bucket list. Have you done any of them already?
48~ Do you have any siblings? Are you close to your family?
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?
38~ Share your most embarrassing sexual memory?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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)
1~ How old were you when you had your first kiss? Who? Care to Share?
34~ Do you like the lights on or off during sex?
22- Do you have any birth marks? How about scars? Care to share how you got them?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
15~ Have you ever been “in love”? Who? 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?
52~ What are your hobbies?
10- List 5 of your top pet peeves.
29- How superstitious are you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
44~ Care to share something about yourself that no one else knows about you?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
12- What’s your favorite food? What’s your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
1- What’s your favorite animal? Do you a least favorite?
81~ Do you have any kinks and/or fetishes?
Please share Did you stop?
If you win, what will you make them do?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
21~ What was the best date you ever went on? What has been the worst?
Do you like the “69” position? Do you prefer to be on top or bottom?
9~ How many times over your lifetime do you think you have had sex so far?
19- What’s your favorite fairytale? What’s your least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
2- What’s your favorite color? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
18~ Who/when was your first “crush”?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
23- What is your dream job? What was it as a child?
I would allow you to do it… What would you do to me?
67~ Do you like it when your partner moans and/or is vocal during sex?
10- What is your favorite family tradition? What’s your least favorite?
70~ Would/do you have/like anal sex?
What have you learned about yourself that you did not before this?
How about if they talk dirty and/or call you names?
Doctor/Nurse Stripper/Client
Do you think this brought you closer together?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
80~ Share your top three fantasies/desires. (Be detailed) 😊
1- What was your first impression of me? Has it changed?
What have you learned about me that was new and/or surprising?
51~ What tends to bring a smile to your face?
13- What is the craziest/scariest thing you've ever done?
Any that are a turn off?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Does the thought excite you? Care to share?
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…
39~ What are your love languages?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
4- For a pet, Cat, dog or other?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
36- Do you play video games? What is your favorite? Do you a least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
9- If you could have three wishes, what would they be? Why?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
89~ Do you like taking showers together?
13~ Is there a difference between, making love, having sex, and fucking?
8- What's your favorite flavor of ice cream? Do you a least favorite?
7- What are your thoughts on religion? Is there an afterlife?
If NO, would you ever have one? Would it be with 2 men or 2 women?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Nothing too Serious
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?
How old are you? Male or Female?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
50~ How many children do you have? What are their ages?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
31- If given a chance to be immortal, would you take it? Why?
19~ Who/when was your first “heartbreak”?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would you mind if your partner watched it? How about together vs alone?
53~ How much can you tell me about the one thing you are most passionate about?
14- What is an embarrassing moment in your life? How about your most embarrassing?
42~ What’s your biggest regret in life?
71~ Would you give your partner a hand or foot job? Would you receive one?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
33- If you could visit any time period, when would you pick? Please explain why?
11- What's your favorite restaurant? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
76~ Have you had a threesome? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
What would you say to prove to yourself that it was really you?
34- Ever been to a concert? What was your favorite? Who would you like to see?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Over time has your thoughts on sex changed?
49~ How many times have you been married? Why did they end?
11- How about if they like a certain sports team? 12-How about drinking too much?
20- What’s your favorite candy? What’s your least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
65~ Describe the best orgasm you’ve ever had? Care to share?
21- What's your favorite way to spend a weekend or time off?
Model/Photographer Police/Criminal
32- What's your greatest talent? Can I see it right now?
*** Random Questions ***
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you watch it? What is your favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
83~ How do you feel about Porn?
You know that I will be 100% truthful, so ask.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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 many partners have you had oral sex with? Who? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
92~ Have you ever had or have an STD? How many? What was it?
61~ How willing would you be to try new sexual positions?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
22- What is your favorite childhood memory? What is your least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Family Relation Age Play
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?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Repairman/Lonely Wife Virgin/Experienced
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Prisoner/Prison Guard Landlord/Tenant
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
40~ What’s the weirdest place you’ve ever had sex?
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,
What is your favorite position? Why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
36~ What is your favorite time of day to have sex/make love?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Do you have a favorite? Is it ok if your partner does?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
(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…)
45~ How do you feel about me blindfolding you? How about blindfolding me?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
11~ Have you ever been caught by your parents or children or others while having sex?
51~ Are you willing to play adult games with your partner?
10~ How many dates are necessary before you to have sex with someone?
3- What’s your favorite smell? Do you a least favorite?
*** What’s Your Favorite…? ***
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
9- Is there something you’ve always wanted to ask me but you’re afraid?