What is the most interesting question you can ask to get to know someone?
12.06.2025 14:02
8- What are your thoughts on politics?
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
What firsthand information do you have on prisoner-on-prisoner sexual abuse/rape?
If YES, was it with 2 men or 2 women? Did you enjoy it?
6- Do you have dreams? Can you remember them? What do you usually dream about?
51~ Are you willing to play adult games with your partner?
40~ What’s the weirdest place you’ve ever had sex?
15- What's your favorite saying? What word or phrase is your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
30~ What's something unexpected that turns you on?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
44~ Care to share something about yourself that no one else knows about you?
*** Questions about Relationships/Past ***
Apple updates design resources for iOS 26, iPadOS 26, and macOS Tahoe 26 - 9to5Mac
How old are you? Male or Female?
10- What is your favorite family tradition? What’s your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Common Diabetes Drug Linked to 'Exceptional Longevity' in Women - ScienceAlert
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Do you think this brought you closer together?
34- Ever been to a concert? What was your favorite? Who would you like to see?
5~ When you first started having sex, was it what you thought it would be?
Derek Jeter Shares Brutal Reality for Yankees After Dodgers Loss - Sports Illustrated
11- What's your favorite restaurant? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
61~ How willing would you be to try new sexual positions?
10~ How many dates are necessary before you to have sex with someone?
If you say it, I will stop, and we can talk about it when you are ready.
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?
AI-Focused Apple Music Reboot Said to Be in the Works - MacRumors
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
Enhanced Box Score: Cubs 2, Reds 0 – May 31, 2025 - Bleacher Nation
22- What is your favorite childhood memory? What is your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Anthony Richardson sidelined by shoulder injury - NBC Sports
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
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?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
ChatGPT outage shows just how many people are using AI at work - MarketWatch
52~ What are your hobbies?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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)
Get this wrong and this could mean the end… :-) some funny, some not…
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
48~ Have you ever paid or been paid for sex?
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
17- Have you ever done drugs? Which ones? How often?
84~ How do you feel about reading/listening to adult stories?
Have you ever? Care to Share?
47~ What would be your dream job and why?
If yes, what?
* Give a rating for each one (0-100)
Would you read them together?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Any that are a turn off?
83~ How do you feel about Porn?
60~ How important is oral sex? Do you like receiving? Do you like giving?
9- Is there something you’ve always wanted to ask me but you’re afraid?
39~ What are your love languages?
28~ What are some things that turn on? What is your biggest turn on?
26~ What side of the bed do you sleep on?
*** Random Questions ***
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Escort/Client Job Applicant/Hiring Manager
13- How about having a certain hair cut/style?
71~ Would you give your partner a hand or foot job? Would you receive one?
Teacher/Student Stranger/One Night Stand
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
62~ Have you used adult toys?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Will you cheat again? How can, you be sure? Define what cheating is to you.
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What have you learned about me that was new and/or surprising?
11- List at least 5 things on your bucket list. Have you done any of them already?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Would you ever want to be woken up with oral and/or intercourse?
How many partners have you had oral sex with? Who? Care to Share?
Do you watch it? What is your favorite?
What is your favorite position? Why?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
3- What was the most surprising thing you’ve learned about me throughout our relationship?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
12- What is the weirdest thing you've ever eaten?
Would you allow me to clean every part of your body with my soapy hands and fingers?
21~ What was the best date you ever went on? What has been the worst?
29- How superstitious are you?
Family Relation Age Play
Will you kiss after your partner has gone down on you? Swallow or spit semen?
32- What's your greatest talent? Can I see it right now?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Model/Photographer Police/Criminal
33- If you could visit any time period, when would you pick? Please explain why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
36~ What is your favorite time of day to have sex/make love?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
17- What’s your favorite holiday? What’s your least favorite?
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Doctor/Nurse Stripper/Client
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?
Nurse/Patient Celebrity/Fan
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Nothing too Serious
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
49~ How many times have you been married? Why did they end?
53~ How much can you tell me about the one thing you are most passionate about?
13~ Is there a difference between, making love, having sex, and fucking?
19- Do/have you smoked? What do you prefer? How often?
Over time has your thoughts on sex changed?
3- What Superhero or Superpower would you want to be/have?
What would you say to prove to yourself that it was really you?
25~ How do you feel about PDA? (Public Display of Affection)
15~ Have you ever been “in love”? Who? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
*** Deal Breaker Questions ***
38~ Share your most embarrassing sexual memory?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
51~ What tends to bring a smile to your face?
Please share Did you stop?
What is your favorite toy? Ever wanted to try a specific toy?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
1- What was your first impression of me? Has it changed?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
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)
18~ Who/when was your first “crush”?
27- What was/ is nickname? Does it have a meaning behind it?
23- What is your dream job? What was it as a child?
82~ Do you have any fantasies involving Role-Playing?
That one or two things that made you go hmmmm, OMG or wow!
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?
9- What’s your favorite season and why? What’s your least favorite?
Any that are a turn off?
42~ What’s your biggest regret in life?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Can you Deep Throat? Do you like the taste of yourself?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
29~ What are some things that turn you off? What is your biggest turn off?
21- What's your favorite way to spend a weekend or time off?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
How about if they talk dirty and/or call you names?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
36- Do you play video games? What is your favorite? Do you a least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
8- What's your favorite flavor of ice cream? Do you a least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
13- What is the craziest/scariest thing you've ever done?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
37- Do you like your name? If you could change it, what would you change it too?
14- What's your favorite dessert? Do you a least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
4- For a pet, Cat, dog or other?
*** Questions About Me ***
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would /have you ever given your partner a lap dance and Striptease?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
What was the longest? What was the shortest?
9~ How many times over your lifetime do you think you have had sex so far?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Repairman/Lonely Wife Virgin/Experienced
81~ Do you have any kinks and/or fetishes?
7- What if a person smells a certain way? 8- How about smoking?
67~ Do you like it when your partner moans and/or is vocal during sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What do you dislike about me? I asked you to be 100% honest.
12- What’s your favorite food? What’s your least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
7- What are your thoughts on religion? Is there an afterlife?
What have you learned about yourself that you did not before this?
If you win, what will you make them do?
(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…)
11- How about if they like a certain sports team? 12-How about drinking too much?
I would allow you to do it… What would you do to me?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
15- What bad habit do you wish you could quit? Do you have any addictions?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Would you mind if your partner watched it? How about together vs alone?
48~ Do you have any siblings? Are you close to your family?
5- Have you ever been hypnotized? Would you allow yourself to be?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Master/Slave Boss/Maid
33- Beach or Mountains? Or is there another place to like better?
Do you have a favorite? Is it ok if your partner does?
28- What are some things that people do that irritate you?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Does the thought excite you? Care to share?
31- If given a chance to be immortal, would you take it? Why?
3- What’s your favorite smell? Do you a least favorite?
34~ Do you like the lights on or off during sex?
2- What’s your favorite color? Do you a least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
How well do you know me? And some of your thoughts about me
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…
18- How often do you drink alcohol? What is your favorite drink?
How many times do you think you have “made love”?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
You know that I will be 100% truthful, so ask.
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
70~ Would/do you have/like anal sex?
20- What’s your favorite candy? What’s your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
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,
1- What’s your favorite animal? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
89~ Do you like taking showers together?
Do you like the “69” position? Do you prefer to be on top or bottom?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
13- What’s your favorite drink? What’s your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
41~ Are there moments in your past that you would want to change? Please share 3 of them.
10- List 5 of your top pet peeves.
The Ice Breaker Questions
1~ How old were you when you had your first kiss? Who? Care to Share?
50~ How many children do you have? What are their ages?
9- If you could have three wishes, what would they be? Why?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you like it when they show and tell you what they want?
Prisoner/Prison Guard Landlord/Tenant
Would you do it again, and would you rather 2 females or 2 males?
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~ Who/when was your first “heartbreak”?
*** What’s Your Favorite…? ***
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?