What is the most interesting question you can ask to get to know someone?
09.06.2025 17:09
11~ Have you ever been caught by your parents or children or others while having sex?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
FDA chief wary of federal recommendations for Covid-19 vaccines - Politico
10- List 5 of your top pet peeves.
11- List at least 5 things on your bucket list. Have you done any of them already?
27- What was/ is nickname? Does it have a meaning behind it?
Ireland added to list of countries monitored by the U.S. for currency manipulation - Fortune
What would you say to prove to yourself that it was really you?
*** What’s Your Favorite…? ***
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Why do unattractive men assume that a pretty woman like me want them?
18~ Who/when was your first “crush”?
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…
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
The Best Tea for Lowering High Blood Pressure, Recommended by a Dietitian - EatingWell
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Apple’s leaked 45W MagSafe charger is first to support Qi2.2 - The Verge
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
36- Do you play video games? What is your favorite? Do you a least favorite?
Do conservative white women like black men?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Why do I feel bad when I see white girls dating black guys, am I racist?
29- How superstitious are you?
13- What’s your favorite drink? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
My ex got into a relationship within 2 weeks after a breakup. What should I do?
Nothing too Serious
22~ What is the best pickup line anyone has ever used on you? What was the worst?
40~ What’s the weirdest place you’ve ever had sex?
7- What are your thoughts on religion? Is there an afterlife?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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What was the longest? What was the shortest?
* Give a rating for each one (0-100)
Escort/Client Job Applicant/Hiring Manager
Why do people love to live alone in a house?
What is your favorite toy? Ever wanted to try a specific toy?
4- For a pet, Cat, dog or other?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Measles cases see biggest rise in over a month - The Hill
Do you think this brought you closer together?
13- What is the craziest/scariest thing you've ever done?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
With 'I Love Lucy' and beyond, Desi Arnaz helped shaped TV as we know it - NPR
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
26~ What side of the bed do you sleep on?
50~ How many children do you have? What are their ages?
PlayStation Plus new free game is the service's first 'AAAA' - GAMINGbible
Any that are a turn off?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
48~ Have you ever paid or been paid for sex?
Do you have a favorite? Is it ok if your partner does?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Can you Deep Throat? Do you like the taste of yourself?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
80~ Share your top three fantasies/desires. (Be detailed) 😊
If you say it, I will stop, and we can talk about it when you are ready.
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
(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?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Model/Photographer Police/Criminal
Doctor/Nurse Stripper/Client
What have you learned about me that was new and/or surprising?
47~ What would be your dream job and why?
Get this wrong and this could mean the end… :-) some funny, some not…
The Ice Breaker Questions
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What is your favorite position? Why?
76~ Have you had a threesome? Care to Share?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
How well do you know me? And some of your thoughts about me
8- What's your favorite flavor of ice cream? Do you a least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
53~ How much can you tell me about the one thing you are most passionate about?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
19- Do/have you smoked? What do you prefer? How often?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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.
What have you learned about yourself that you did not before this?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
81~ Do you have any kinks and/or fetishes?
14- What is an embarrassing moment in your life? How about your most embarrassing?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
22- What is your favorite childhood memory? What is your least favorite?
14- What's your favorite dessert? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
8- What are your thoughts on politics?
89~ Do you like taking showers together?
7-What do I do in bed that drives you wild? How about, what turns you off?
33- If you could visit any time period, when would you pick? Please explain why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
15- What bad habit do you wish you could quit? Do you have any addictions?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
How many times do you think you have “made love”?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
7- What if a person smells a certain way? 8- How about smoking?
10- What is your favorite family tradition? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would you ever want to be woken up with oral and/or intercourse?
11- How about if they like a certain sports team? 12-How about drinking too much?
29~ What are some things that turn you off? What is your biggest turn off?
Prisoner/Prison Guard Landlord/Tenant
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Do you watch it? What is your favorite?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
21~ What was the best date you ever went on? What has been the worst?
10~ How many dates are necessary before you to have sex with someone?
52~ What are your hobbies?
51~ Are you willing to play adult games with your partner?
That one or two things that made you go hmmmm, OMG or wow!
49~ If you could, would you want to be the opposite sex for a day, week, or year?
32- What's your greatest talent? Can I see it right now?
15~ Have you ever been “in love”? Who? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
83~ How do you feel about Porn?
How many partners have you had oral sex with? Who? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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…
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
12- What is the weirdest thing you've ever eaten?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
17- Have you ever done drugs? Which ones? How often?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
60~ How important is oral sex? Do you like receiving? Do you like giving?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
49~ How many times have you been married? Why did they end?
38~ Share your most embarrassing sexual memory?
Would /have you ever given your partner a lap dance and Striptease?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
30~ What's something unexpected that turns you on?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What do you dislike about me? I asked you to be 100% honest.
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
3- What Superhero or Superpower would you want to be/have?
If NO, would you ever have one? Would it be with 2 men or 2 women?
62~ Have you used adult toys?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
1- What was your first impression of me? Has it changed?
9- What’s your favorite season and why? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
52~ Are you willing to make “those types” of bets with your partner?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
(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…)
Do you like it when they show and tell you what they want?
37- Do you like your name? If you could change it, what would you change it too?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Have you ever? Care to Share?
How old are you? Male or Female?
12- What’s your favorite food? What’s your least favorite?
Would you read them together?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
17- What’s your favorite holiday? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
51~ What tends to bring a smile to your face?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
If yes, what?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Nurse/Patient Celebrity/Fan
*** Questions about Relationships/Past ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
34~ Do you like the lights on or off during sex?
45~ How do you feel about me blindfolding you? How about blindfolding me?
What is your view on sex? Meaning, When/Where/ How often/
Repairman/Lonely Wife Virgin/Experienced
67~ Do you like it when your partner moans and/or is vocal during sex?
48~ Do you have any siblings? Are you close to your family?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
If you win, what will you make them do?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Do you like the “69” position? Do you prefer to be on top or bottom?
18- How often do you drink alcohol? What is your favorite drink?
5- Have you ever been hypnotized? Would you allow yourself to be?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
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?
9~ How many times over your lifetime do you think you have had sex so far?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
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?
Please share Did you stop?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
19- What’s your favorite fairytale? What’s your least favorite?
Does the thought excite you? Care to share?
6- Do you have dreams? Can you remember them? What do you usually dream about?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
36~ What is your favorite time of day to have sex/make love?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
39~ What are your love languages?
20- What’s your favorite candy? What’s your least favorite?
23- What is your dream job? What was it as a child?
You know that I will be 100% truthful, so ask.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
9- If you could have three wishes, what would they be? Why?
Family Relation Age Play
Over time has your thoughts on sex changed?
2- What’s your favorite color? Do you a least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
*** Questions About Me ***
92~ Have you ever had or have an STD? How many? What was it?
42~ What’s your biggest regret in life?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
21- What's your favorite way to spend a weekend or time off?
How about if they talk dirty and/or call you names?
19~ Who/when was your first “heartbreak”?
Would you do it again, and would you rather 2 females or 2 males?
61~ How willing would you be to try new sexual positions?
13~ Is there a difference between, making love, having sex, and fucking?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
70~ Would/do you have/like anal sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
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,
*** Deal Breaker Questions ***
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
11- What's your favorite restaurant? What’s your least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
3- What’s your favorite smell? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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)
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Master/Slave Boss/Maid
28- What are some things that people do that irritate you?
Will you cheat again? How can, you be sure? Define what cheating is to you.
65~ Describe the best orgasm you’ve ever had? Care to share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
82~ Do you have any fantasies involving Role-Playing?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
*** Random Questions ***
34- Ever been to a concert? What was your favorite? Who would you like to see?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
1- What’s your favorite animal? Do you a least favorite?
33- Beach or Mountains? Or is there another place to like better?
Any that are a turn off?
Would you mind if your partner watched it? How about together vs alone?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
92~ Everyone needs a “safe” word. What is yours?
If YES, was it with 2 men or 2 women? Did you enjoy it?
28~ What are some things that turn on? What is your biggest turn on?
I would allow you to do it… What would you do to me?