What is the most interesting question you can ask to get to know someone?
13.06.2025 00:29
9- Is there something you’ve always wanted to ask me but you’re afraid?
If you say it, I will stop, and we can talk about it when you are ready.
83~ How do you feel about Porn?
Musk-Trump Spat Hits New High As Musk’s Ex Piles On - HuffPost
13- How about having a certain hair cut/style?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Speech by Governor Kugler on the economic outlook and monetary policy - Federal Reserve Board (.gov)
Over time has your thoughts on sex changed?
Prisoner/Prison Guard Landlord/Tenant
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
JPMorgan's Jamie Dimon Says U.S. Should Stockpile Missiles, Not Bitcoin - CoinDesk
17- Have you ever done drugs? Which ones? How often?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
3- What’s your favorite smell? Do you a least favorite?
Have you ever had your crush reject you, and then later you all dated and married?
81~ Do you have any kinks and/or fetishes?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Why does Africa have all mineral resources but she is suffering economically?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you like the “69” position? Do you prefer to be on top or bottom?
R.I.P Loretta Swit: How well do you remember ''Hot Lips'' Houlihan? - MeTV
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
17- What’s your favorite holiday? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
What is the most inappropriate experience you have had with a friend's daughter?
Have you ever? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
10~ How many dates are necessary before you to have sex with someone?
Why do boobs of some girls bounce when they walk?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
61~ How willing would you be to try new sexual positions?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
28- What are some things that people do that irritate you?
What do you dislike about me? I asked you to be 100% honest.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
GOP megabill could undermine US energy production, Republicans warn - Politico
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
If there is an abandoned house with no owner, can I live in it?
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
89~ Do you like taking showers together?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Any that are a turn off?
12- What’s your favorite food? What’s your least favorite?
Live From: 125th U.S. Open Championship Final Qualifying - Metropolitan Golf Association
70~ Would/do you have/like anal sex?
32- What's your greatest talent? Can I see it right now?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How can we become the best humans? How can we trust each other?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
27- What was/ is nickname? Does it have a meaning behind it?
33- If you could visit any time period, when would you pick? Please explain why?
Do very hot men ever feel attracted to an ugly woman? Why?
*** Deal Breaker Questions ***
5~ When you first started having sex, was it what you thought it would be?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
15~ Have you ever been “in love”? Who? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
82~ Do you have any fantasies involving Role-Playing?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Nurse/Patient Celebrity/Fan
53~ How much can you tell me about the one thing you are most passionate about?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
If you win, what will you make them do?
60~ How important is oral sex? Do you like receiving? Do you like giving?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Nothing too Serious
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
80~ Share your top three fantasies/desires. (Be detailed) 😊
If you lose, are you willing to be their sex slave for a day, (anything goes)?
14- What's your favorite dessert? Do you a least favorite?
49~ How many times have you been married? Why did they end?
18~ Who/when was your first “crush”?
*** Questions about Relationships/Past ***
33- Beach or Mountains? Or is there another place to like better?
3- Should Pluto still be considered a planet? 4- How about smoking?
71~ Would you give your partner a hand or foot job? Would you receive one?
What was the longest? What was the shortest?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Doctor/Nurse Stripper/Client
40~ What’s the weirdest place you’ve ever had sex?
19~ Who/when was your first “heartbreak”?
21~ What was the best date you ever went on? What has been the worst?
28~ What are some things that turn on? What is your biggest turn on?
12- What is the weirdest thing you've ever eaten?
29- How superstitious are you?
48~ Have you ever paid or been paid for sex?
62~ Have you used adult toys?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
52~ What are your hobbies?
7- What are your thoughts on religion? Is there an afterlife?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
76~ Have you had a threesome? Care to Share?
Master/Slave Boss/Maid
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…
3- What was the most surprising thing you’ve learned about me throughout our relationship?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
10- What is your favorite family tradition? What’s your least favorite?
Do you like it when they show and tell you what they want?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
31- If given a chance to be immortal, would you take it? Why?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
22- What is your favorite childhood memory? What is your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
You know that I will be 100% truthful, so ask.
Will you cheat again? How can, you be sure? Define what cheating is to you.
36~ What is your favorite time of day to have sex/make love?
Would you mind if your partner watched it? How about together vs alone?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
9- What’s your favorite season and why? What’s your least favorite?
34~ Do you like the lights on or off during sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
39~ What are your love languages?
Teacher/Student Stranger/One Night Stand
45~ How do you feel about me blindfolding you? How about blindfolding me?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
51~ Are you willing to play adult games with your partner?
What is your favorite toy? Ever wanted to try a specific toy?
If yes, what?
13- What’s your favorite drink? What’s your least favorite?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
5- Have you ever been hypnotized? Would you allow yourself to be?
34- Ever been to a concert? What was your favorite? Who would you like to see?
9~ How many times over your lifetime do you think you have had sex so far?
50~ How many children do you have? What are their ages?
Would you read them together?
21- What's your favorite way to spend a weekend or time off?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
(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…)
Family Relation Age Play
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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…
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?
Would you ever want to be woken up with oral and/or intercourse?
If YES, was it with 2 men or 2 women? Did you enjoy it?
1~ How old were you when you had your first kiss? Who? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Do you have a favorite? Is it ok if your partner does?
Can you Deep Throat? Do you like the taste of yourself?
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,
13~ Is there a difference between, making love, having sex, and fucking?
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How many partners have you had oral sex with? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
13- What is the craziest/scariest thing you've ever done?
29~ What are some things that turn you off? What is your biggest turn off?
48~ Do you have any siblings? Are you close to your family?
2- What’s your favorite color? 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.
64~ When was your very first orgasm? When was your first from having sex? Care to share?
67~ Do you like it when your partner moans and/or is vocal during sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8- What are your thoughts on politics?
Do you think this brought you closer together?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Any that are a turn off?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
44~ Care to share something about yourself that no one else knows about you?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Would /have you ever given your partner a lap dance and Striptease?
What would you say to prove to yourself that it was really you?
92~ Have you ever had or have an STD? How many? What was it?
52~ Are you willing to make “those types” of bets with your partner?
26~ What side of the bed do you sleep on?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
19- Do/have you smoked? What do you prefer? How often?
Please share Did you stop?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
11- What's your favorite restaurant? What’s your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
30~ What's something unexpected that turns you on?
If NO, would you ever have one? Would it be with 2 men or 2 women?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
11~ Have you ever been caught by your parents or children or others while having sex?
* Give a rating for each one (0-100)
What have you learned about me that was new and/or surprising?
Do you watch it? What is your favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
*** Random Questions ***
I would allow you to do it… What would you do to me?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
6- Do you have dreams? Can you remember them? What do you usually dream about?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
22- Do you have any birth marks? How about scars? Care to share how you got them?
9- If you could have three wishes, what would they be? Why?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
15- What's your favorite saying? What word or phrase is your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
42~ What’s your biggest regret in life?
1- What was your first impression of me? Has it changed?
*** What’s Your Favorite…? ***
1- What’s your favorite animal? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
The Ice Breaker Questions
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
23- What is your dream job? What was it as a child?
36- Do you play video games? What is your favorite? Do you a least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
47~ What would be your dream job and why?
What is your view on sex? Meaning, When/Where/ How often/
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?
10- List 5 of your top pet peeves.
4- For a pet, Cat, dog or other?
*** Questions About Me ***
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
What is your favorite position? Why?
38~ Share your most embarrassing sexual memory?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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?
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?
51~ What tends to bring a smile to your face?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3- What Superhero or Superpower would you want to be/have?
Get this wrong and this could mean the end… :-) some funny, some not…
Repairman/Lonely Wife Virgin/Experienced
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How well do you know me? And some of your thoughts about me
25~ How do you feel about PDA? (Public Display of Affection)
Does the thought excite you? Care to share?
11- How about if they like a certain sports team? 12-How about drinking too much?
How many times do you think you have “made love”?
How about if they talk dirty and/or call you names?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Model/Photographer Police/Criminal
8- What's your favorite flavor of ice cream? Do you a least favorite?
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?
That one or two things that made you go hmmmm, OMG or wow!
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Would you do it again, and would you rather 2 females or 2 males?
Escort/Client Job Applicant/Hiring Manager
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
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)
What have you learned about yourself that you did not before this?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
37- Do you like your name? If you could change it, what would you change it too?
18- How often do you drink alcohol? What is your favorite drink?
How old are you? Male or Female?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
11- List at least 5 things on your bucket list. Have you done any of them already?