What is the most interesting question you can ask to get to know someone?
Last Updated: 28.06.2025 05:13
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Prisoner/Prison Guard Landlord/Tenant
30~ What's something unexpected that turns you on?
Do you have a favorite? Is it ok if your partner does?
71~ Would you give your partner a hand or foot job? Would you receive one?
9~ How many times over your lifetime do you think you have had sex so far?
A recipe to reverse cancer’s sweet tooth - Cold Spring Harbor Laboratory
Model/Photographer Police/Criminal
Do you watch it? What is your favorite?
84~ How do you feel about reading/listening to adult stories?
*** Deal Breaker Questions ***
If you win, what will you make them do?
3- What Superhero or Superpower would you want to be/have?
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How long for foreplay? Do you need to have an orgasm? Is afterplay important?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would you mind if your partner watched it? How about together vs alone?
Hundreds of Mysterious Giant Viruses Discovered Lurking in The Ocean - ScienceAlert
How many times do you think you have “made love”?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Keir Starmer calls for Iran to return to negotiating table - BBC
28~ What are some things that turn on? What is your biggest turn on?
(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…)
9- Is there something you’ve always wanted to ask me but you’re afraid?
22- Do you have any birth marks? How about scars? Care to share how you got them?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
What is your opinion on the band Nickelback? Why do they receive criticism from some people?
Please share Did you stop?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How old are you? Male or Female?
1- What’s your favorite animal? Do you a least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
That one or two things that made you go hmmmm, OMG or wow!
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(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
33- Beach or Mountains? Or is there another place to like better?
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1~ How old were you when you had your first kiss? Who? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you like it when they show and tell you what they want?
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?
What would you say to prove to yourself that it was really you?
Most people aren’t following this important dietary advice. Are you? - The Washington Post
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Real TikTokers are pretending to be Veo 3 AI creations for fun, attention - Ars Technica
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- Should Pluto still be considered a planet? 4- How about smoking?
Night Owls Face Faster Cognitive Decline - Neuroscience News
31- If given a chance to be immortal, would you take it? Why?
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)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
7- What are your thoughts on religion? Is there an afterlife?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
If you say it, I will stop, and we can talk about it when you are ready.
34- Ever been to a concert? What was your favorite? Who would you like to see?
83~ How do you feel about Porn?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
51~ What tends to bring a smile to your face?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
12- What is the weirdest thing you've ever eaten?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
60~ How important is oral sex? Do you like receiving? Do you like giving?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
6- What’s your favorite TV series? Do you have a favorite genre? 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?
13- What’s your favorite drink? What’s your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
81~ Do you have any kinks and/or fetishes?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
8- What are your thoughts on politics?
82~ Do you have any fantasies involving Role-Playing?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
92~ Have you ever had or have an STD? How many? What was it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
42~ What’s your biggest regret in life?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Over time has your thoughts on sex changed?
47~ What would be your dream job and why?
21~ What was the best date you ever went on? What has been the worst?
Nothing too Serious
48~ Do you have any siblings? Are you close to your family?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Master/Slave Boss/Maid
Do you like the “69” position? Do you prefer to be on top or bottom?
Can you Deep Throat? Do you like the taste of yourself?
89~ Do you like taking showers together?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Nurse/Patient Celebrity/Fan
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Have you ever? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
52~ What are your hobbies?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
22- What is your favorite childhood memory? What is your least favorite?
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?
1- What was your first impression of me? Has it changed?
18- How often do you drink alcohol? What is your favorite drink?
What is your favorite toy? Ever wanted to try a specific toy?
3- What’s your favorite smell? Do you a least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
62~ Have you used adult toys?
36- Do you play video games? What is your favorite? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
50~ How many children do you have? What are their ages?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Would you read them together?
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?
What have you learned about me that was new and/or surprising?
32- What's your greatest talent? Can I see it right now?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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?
10~ How many dates are necessary before you to have sex with someone?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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…
Doctor/Nurse Stripper/Client
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
28- What are some things that people do that irritate you?
14- What's your favorite dessert? Do you a least favorite?
48~ Have you ever paid or been paid for 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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
40~ What’s the weirdest place you’ve ever had sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
13- How about having a certain hair cut/style?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
34~ Do you like the lights on or off during sex?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
19- What’s your favorite fairytale? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How well do you know me? And some of your thoughts about me
5- Have you ever been hypnotized? Would you allow yourself to be?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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,
Escort/Client Job Applicant/Hiring Manager
How many partners have you had oral sex with? Who? Care to Share?
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?
33- If you could visit any time period, when would you pick? Please explain why?
If NO, would you ever have one? Would it be with 2 men or 2 women?
What have you learned about yourself that you did not before this?
27- What was/ is nickname? Does it have a meaning behind it?
52~ Are you willing to make “those types” of bets with your partner?
20- What’s your favorite candy? What’s your least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
26~ What side of the bed do you sleep on?
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
I would allow you to do it… What would you do to me?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Would you do it again, and would you rather 2 females or 2 males?
Any that are a turn off?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
51~ Are you willing to play adult games with your partner?
5~ When you first started having sex, was it what you thought it would be?
Teacher/Student Stranger/One Night Stand
What do you dislike about me? I asked you to be 100% honest.
17- What’s your favorite holiday? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
* Give a rating for each one (0-100)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
39~ What are your love languages?
What was the longest? What was the shortest?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
67~ Do you like it when your partner moans and/or is vocal during sex?
11~ Have you ever been caught by your parents or children or others while having sex?
9- If you could have three wishes, what would they be? Why?
61~ How willing would you be to try new sexual positions?
29- How superstitious are you?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
4- For a pet, Cat, dog or other?
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
You know that I will be 100% truthful, so ask.
Repairman/Lonely Wife Virgin/Experienced
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
19~ Who/when was your first “heartbreak”?
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?
13- What is the craziest/scariest thing you've ever done?
45~ How do you feel about me blindfolding you? How about blindfolding me?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
15~ Have you ever been “in love”? Who? Care to Share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
2- What’s your favorite color? Do you a least favorite?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
*** Questions About Me ***
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?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
If yes, what?
76~ Have you had a threesome? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
65~ Describe the best orgasm you’ve ever had? Care to share?
How about if they talk dirty and/or call you names?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
21- What's your favorite way to spend a weekend or time off?
Any that are a turn off?
38~ Share your most embarrassing sexual memory?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
11- How about if they like a certain sports team? 12-How about drinking too much?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Would /have you ever given your partner a lap dance and Striptease?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
7-What do I do in bed that drives you wild? How about, what turns you off?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would you ever want to be woken up with oral and/or intercourse?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
53~ How much can you tell me about the one thing you are most passionate about?
19- Do/have you smoked? What do you prefer? How often?
49~ How many times have you been married? Why did they end?
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?
*** Random Questions ***
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
44~ Care to share something about yourself that no one else knows about you?
What is your view on sex? Meaning, When/Where/ How often/
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
The Ice Breaker Questions
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?
25~ How do you feel about PDA? (Public Display of Affection)
13~ Is there a difference between, making love, having sex, and fucking?
92~ Everyone needs a “safe” word. What is yours?
12- What’s your favorite food? What’s your least favorite?
What is your favorite position? Why?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
10- List 5 of your top pet peeves.
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you think this brought you closer together?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
9- What’s your favorite season and why? What’s your least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Family Relation Age Play
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
23- What is your dream job? What was it as a child?
*** What’s Your Favorite…? ***
*** Questions about Relationships/Past ***
17- Have you ever done drugs? Which ones? How often?
18~ Who/when was your first “crush”?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
10- What is your favorite family tradition? What’s your least favorite?
70~ Would/do you have/like anal sex?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
80~ Share your top three fantasies/desires. (Be detailed) 😊