What is the most interesting question you can ask to get to know someone?
08.06.2025 14:23
64~ When was your very first orgasm? When was your first from having sex? Care to share?
15- What bad habit do you wish you could quit? Do you have any addictions?
Do you like it when they show and tell you what they want?
23- What is your dream job? What was it as a child?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
47~ What would be your dream job and why?
If you say it, I will stop, and we can talk about it when you are ready.
13- How about having a certain hair cut/style?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Simulations Show What Really Happens When a Black Hole Devours a Neutron Star - Gizmodo
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Master/Slave Boss/Maid
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Why are women attracted to ugly guys?
How many partners have you had oral sex with? Who? Care to Share?
You know that I will be 100% truthful, so ask.
13- What is the craziest/scariest thing you've ever done?
Why after 50 years of being straight do I constantly desire to suck cock?
Doctor/Nurse Stripper/Client
2- What’s your favorite color? Do you a least favorite?
48~ Do you have any siblings? Are you close to your family?
Bill Oram: Seriously, who is going to beat the Beavers? - OregonLive.com
15~ Have you ever been “in love”? Who? Care to Share?
*** Deal Breaker Questions ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
What is the reason for writing X^2 as XX instead of X*X?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
26~ What side of the bed do you sleep on?
How do I get over a long-term relationship breakup?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Would you mind if your partner watched it? How about together vs alone?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
This Genetic ‘Trick’ Helped the Black Death Linger for Centuries - Gizmodo
What have you learned about me that was new and/or surprising?
10- What is your favorite family tradition? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
DOOM: The Dark Ages | Update 1 Release Notes - Slayers Club
38~ Share your most embarrassing sexual memory?
51~ Are you willing to play adult games with your partner?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
49~ How many times have you been married? Why did they end?
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?
What CIA front organizations operated in the United States during the 1960s?
*** Questions About Me ***
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Will you cheat again? How can, you be sure? Define what cheating is to you.
If NO, would you ever have one? Would it be with 2 men or 2 women?
28~ What are some things that turn on? What is your biggest turn on?
36- Do you play video games? What is your favorite? Do you a least favorite?
Race and genetics do not line up well, new study confirms - Live Science
What was the longest? What was the shortest?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Have you ever? Care to Share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
31- If given a chance to be immortal, would you take it? Why?
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?
33- Beach or Mountains? Or is there another place to like better?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
92~ Everyone needs a “safe” word. What is yours?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Teacher/Student Stranger/One Night Stand
What is your view on sex? Meaning, When/Where/ How often/
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Nothing too Serious
21- What's your favorite way to spend a weekend or time off?
52~ What are your hobbies?
The Ice Breaker Questions
46~ Have you ever used furniture, or other types of things to aid you while having sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
12- What’s your favorite food? What’s your least favorite?
62~ Have you used adult toys?
82~ Do you have any fantasies involving Role-Playing?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
* Give a rating for each one (0-100)
15- What's your favorite saying? What word or phrase is your least favorite?
Family Relation Age Play
19~ Who/when was your first “heartbreak”?
21~ What was the best date you ever went on? What has been the worst?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12- What is the weirdest thing you've ever eaten?
18~ Who/when was your first “crush”?
Do you have a favorite? Is it ok if your partner does?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
3- Should Pluto still be considered a planet? 4- How about smoking?
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…
28- What are some things that people do that irritate you?
11~ Have you ever been caught by your parents or children or others while having sex?
50~ How many children do you have? What are their ages?
9- If you could have three wishes, what would they be? Why?
67~ Do you like it when your partner moans and/or is vocal during sex?
14- What's your favorite dessert? Do you a least favorite?
76~ Have you had a threesome? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
34~ Do you like the lights on or off during sex?
If yes, what?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
81~ Do you have any kinks and/or fetishes?
How about if they talk dirty and/or call you names?
4- For a pet, Cat, dog or other?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
1- What’s your favorite animal? Do you a least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
If YES, was it with 2 men or 2 women? Did you enjoy it?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
30~ What's something unexpected that turns you on?
22- What is your favorite childhood memory? What is your least favorite?
Do you watch it? What is your favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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?
8- What are your thoughts on politics?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
42~ What’s your biggest regret in life?
61~ How willing would you be to try new sexual positions?
40~ What’s the weirdest place you’ve ever had sex?
How well do you know me? And some of your thoughts about me
89~ Do you like taking showers together?
Would you do it again, and would you rather 2 females or 2 males?
65~ Describe the best orgasm you’ve ever had? Care to share?
51~ What tends to bring a smile to your face?
*** Questions about Relationships/Past ***
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
10~ How many dates are necessary before you to have sex with someone?
53~ How much can you tell me about the one thing you are most passionate about?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
*** What’s Your Favorite…? ***
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Escort/Client Job Applicant/Hiring Manager
Prisoner/Prison Guard Landlord/Tenant
37- Do you like your name? If you could change it, what would you change it too?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
1- What was your first impression of me? Has it changed?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
39~ What are your love languages?
Please share Did you stop?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would /have you ever given your partner a lap dance and Striptease?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
7- What are your thoughts on religion? Is there an afterlife?
What is your favorite toy? Ever wanted to try a specific toy?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
71~ Would you give your partner a hand or foot job? Would you receive one?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
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…
Can you Deep Throat? Do you like the taste of yourself?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
How many times do you think you have “made love”?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
19- What’s your favorite fairytale? What’s your least favorite?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
5~ When you first started having sex, was it what you thought it would be?
13~ Is there a difference between, making love, having sex, and fucking?
36~ What is your favorite time of day to have sex/make love?
Any that are a turn off?
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…
29~ What are some things that turn you off? What is your biggest turn off?
84~ How do you feel about reading/listening to adult stories?
92~ Have you ever had or have an STD? How many? What was it?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
What do you dislike about me? I asked you to be 100% honest.
8- What's your favorite flavor of ice cream? Do you a least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Nurse/Patient Celebrity/Fan
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
83~ How do you feel about Porn?
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)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
17- Have you ever done drugs? Which ones? How often?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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,
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
What have you learned about yourself that you did not before this?
9- What’s your favorite season and why? What’s your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
45~ How do you feel about me blindfolding you? How about blindfolding me?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
3- What’s your favorite smell? Do you a least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
9~ How many times over your lifetime do you think you have had sex so far?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you read them together?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
I would allow you to do it… What would you do to me?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
3- What Superhero or Superpower would you want to be/have?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
*** Random Questions ***
20- What’s your favorite candy? What’s your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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?
70~ Would/do you have/like anal sex?
32- What's your greatest talent? Can I see it right now?
19- Do/have you smoked? What do you prefer? How often?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
What is your favorite position? Why?
11- How about if they like a certain sports team? 12-How about drinking too much?
29- How superstitious are you?
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?
52~ Are you willing to make “those types” of bets with your partner?
What would you say to prove to yourself that it was really you?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
27- What was/ is nickname? Does it have a meaning behind it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
48~ Have you ever paid or been paid for sex?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Does the thought excite you? Care to share?
10- List 5 of your top pet peeves.
11- What's your favorite restaurant? What’s your least favorite?
5- Have you ever been hypnotized? Would you allow yourself to be?
Over time has your thoughts on sex changed?
That one or two things that made you go hmmmm, OMG or wow!
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Any that are a turn off?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
13- What’s your favorite drink? What’s your least favorite?
(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…)
How old are you? Male or Female?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Repairman/Lonely Wife Virgin/Experienced
Do you think this brought you closer together?
33- If you could visit any time period, when would you pick? Please explain why?
11- List at least 5 things on your bucket list. Have you done any of them already?
22- Do you have any birth marks? How about scars? Care to share how you got them?
17- What’s your favorite holiday? What’s your least favorite?
44~ Care to share something about yourself that no one else knows about you?
If you win, what will you make them do?
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?
7- What if a person smells a certain way? 8- How about smoking?
Would you ever want to be woken up with oral and/or intercourse?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Model/Photographer Police/Criminal