What is the most interesting question you can ask to get to know someone?
Last Updated: 28.06.2025 00:06
13~ Is there a difference between, making love, having sex, and fucking?
3- What’s your favorite smell? Do you a least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
How do military families handle communication when a service member is injured overseas?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Any that are a turn off?
42~ What’s your biggest regret in life?
Global Investors Suddenly Have a New Concern: A U.S. ‘Revenge Tax’ - WSJ
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do 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?
Any that are a turn off?
3- Should Pluto still be considered a planet? 4- How about smoking?
Have you ever? Care to Share?
Full-screen Xbox handheld UI is coming to all Windows PCs “starting next year” - Ars Technica
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
48~ Have you ever paid or been paid for sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Ancient Protein Breaks Biological Rules by Working in a Mirror World - SciTechDaily
1~ How old were you when you had your first kiss? Who? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would /have you ever given your partner a lap dance and Striptease?
You know that I will be 100% truthful, so ask.
Escort/Client Job Applicant/Hiring Manager
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Why is our generation so unhappy?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
21~ What was the best date you ever went on? What has been the worst?
Teacher/Student Stranger/One Night Stand
In the Belly of This Beast, a Major Find - Newser
50~ How many children do you have? What are their ages?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Is it possible to achieve spiritual enlightenment while being in a romantic relationship?
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?
* Give a rating for each one (0-100)
18~ Who/when was your first “crush”?
A father of 3 felt healthy. Then a routine screening found a rare, deadly illness. - CBS News
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
5- Have you ever been hypnotized? Would you allow yourself to be?
Sharpest View of the Sun Reveals Magnetic Stripes the Size of Manhattan - Gizmodo
80~ Share your top three fantasies/desires. (Be detailed) 😊
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Person with measles visited Boston hotel, museum, airport, health officials warn - NBC Boston
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How many times do you think you have “made love”?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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25~ How do you feel about PDA? (Public Display of Affection)
44~ Care to share something about yourself that no one else knows about you?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
How old are you? Male or Female?
Get this wrong and this could mean the end… :-) some funny, some not…
9- If you could have three wishes, what would they be? Why?
Do you think this brought you closer together?
10- What is your favorite family tradition? What’s your least favorite?
Please share Did you stop?
22- Do you have any birth marks? How about scars? Care to share how you got them?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
What would you say to prove to yourself that it was really you?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
70~ Would/do you have/like anal sex?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
Over time has your thoughts on sex changed?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Model/Photographer Police/Criminal
How many partners have you had oral sex with? Who? Care to Share?
61~ How willing would you be to try new sexual positions?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
*** Deal Breaker Questions ***
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…
7- What if a person smells a certain way? 8- How about smoking?
9~ How many times over your lifetime do you think you have had sex so far?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Prisoner/Prison Guard Landlord/Tenant
Will you cheat again? How can, you be sure? Define what cheating is to you.
34~ Do you like the lights on or off during sex?
Can you Deep Throat? Do you like the taste of yourself?
19~ Who/when was your first “heartbreak”?
45~ How do you feel about me blindfolding you? How about blindfolding me?
30~ What's something unexpected that turns you on?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
13- How about having a certain hair cut/style?
51~ What tends to bring a smile to your face?
15- What's your favorite saying? What word or phrase is your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
36~ What is your favorite time of day to have sex/make love?
15~ Have you ever been “in love”? Who? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
The Ice Breaker Questions
How about if they talk dirty and/or call you names?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
What have you learned about yourself that you did not before this?
Master/Slave Boss/Maid
53~ How much can you tell me about the one thing you are most passionate about?
Do you like it when they show and tell you what they want?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
18- How often do you drink alcohol? What is your favorite drink?
Do you like the “69” position? Do you prefer to be on top or bottom?
Repairman/Lonely Wife Virgin/Experienced
28~ What are some things that turn on? What is your biggest turn on?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
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?
If yes, what?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
29~ What are some things that turn you off? What is your biggest turn off?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
10- List 5 of your top pet peeves.
Doctor/Nurse Stripper/Client
49~ If you could, would you want to be the opposite sex for a day, week, or year?
34- Ever been to a concert? What was your favorite? Who would you like to see?
13- What is the craziest/scariest thing you've ever done?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
4- For a pet, Cat, dog or other?
Would you ever want to be woken up with oral and/or intercourse?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
92~ Everyone needs a “safe” word. What is yours?
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?
47~ What would be your dream job and why?
Would you mind if your partner watched it? How about together vs alone?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
1- What was your first impression of me? Has it changed?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
13- What’s your favorite drink? What’s your least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
*** Questions about Relationships/Past ***
31- If given a chance to be immortal, would you take it? Why?
48~ Do you have any siblings? Are you close to your family?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What do you dislike about me? I asked you to be 100% honest.
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
15- What bad habit do you wish you could quit? Do you have any addictions?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
28- What are some things that people do that irritate you?
32- What's your greatest talent? Can I see it right now?
12- What is the weirdest thing you've ever eaten?
33- If you could visit any time period, when would you pick? Please explain why?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
*** Random Questions ***
Would you allow me to clean every part of your body with my soapy hands and fingers?
3- What Superhero or Superpower would you want to be/have?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
(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…)
What is your favorite position? Why?
22- What is your favorite childhood memory? What is your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
What have you learned about me that was new and/or surprising?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
51~ Are you willing to play adult games with your partner?
26~ What side of the bed do you sleep on?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
27- What was/ is nickname? Does it have a meaning behind it?
Would you do it again, and would you rather 2 females or 2 males?
How well do you know me? And some of your thoughts about me
*** Questions About Me ***
Will you kiss after your partner has gone down on you? Swallow or spit semen?
49~ How many times have you been married? Why did they end?
11~ Have you ever been caught by your parents or children or others while having sex?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
83~ How do you feel about Porn?
If you say it, I will stop, and we can talk about it when you are ready.
38~ Share your most embarrassing sexual memory?
62~ Have you used adult toys?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
Nurse/Patient Celebrity/Fan
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
52~ Are you willing to make “those types” of bets with your partner?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
*** What’s Your Favorite…? ***
52~ What are your hobbies?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
14- What's your favorite dessert? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Does the thought excite you? Care to share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
10~ How many dates are necessary before you to have sex with someone?
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?
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 win, what will you make them do?
81~ Do you have any kinks and/or fetishes?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
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~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
29- How superstitious are you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
If YES, was it with 2 men or 2 women? Did you enjoy it?
Do you have a favorite? Is it ok if your partner does?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
82~ Do you have any fantasies involving Role-Playing?
84~ How do you feel about reading/listening to adult stories?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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,
14- What is an embarrassing moment in your life? How about your most embarrassing?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
I would allow you to do it… What would you do to me?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
65~ Describe the best orgasm you’ve ever had? Care to share?
What is your favorite toy? Ever wanted to try a specific toy?
67~ Do you like it when your partner moans and/or is vocal during sex?
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…
19- Do/have you smoked? What do you prefer? How often?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Nothing too Serious
2- What’s your favorite color? Do you a least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
39~ What are your love languages?
Family Relation Age Play
23- What is your dream job? What was it as a child?
11- List at least 5 things on your bucket list. Have you done any of them already?
17- Have you ever done drugs? Which ones? How often?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
33- Beach or Mountains? Or is there another place to like better?
8- What are your thoughts on politics?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
11- How about if they like a certain sports team? 12-How about drinking too much?
Would you read them together?
19- What’s your favorite fairytale? What’s your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
89~ Do you like taking showers together?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
9- What’s your favorite season and why? What’s your least favorite?
Do you watch it? What is your favorite?
12- What’s your favorite food? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
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?
That one or two things that made you go hmmmm, OMG or wow!
76~ Have you had a threesome? Care to Share?
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?
7- What are your thoughts on religion? Is there an afterlife?
21- What's your favorite way to spend a weekend or time off?
What was the longest? What was the shortest?
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?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7-What do I do in bed that drives you wild? How about, what turns you off?