What is the most interesting question you can ask to get to know someone?
08.06.2025 14:18
Nurse/Patient Celebrity/Fan
48~ Have you ever paid or been paid for sex?
(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…)
Weight stigma isn’t just cruel — it makes losing weight harder - CNN
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
89~ Do you like taking showers together?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
52~ Are you willing to make “those types” of bets with your partner?
Would you read them together?
Trump, DOJ threaten Calif. with legal action, fines after trans athlete’s win - The Washington Post
3- What’s your favorite smell? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
Your TRICARE Checklist for Moving - TRICARE Newsroom (.mil)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What is your favorite position? Why?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Why do narcissists avoid talking about the real issues?
33- Beach or Mountains? Or is there another place to like better?
28~ What are some things that turn on? What is your biggest turn on?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
S&P Dow Jones Makes No Changes to S&P 500 in Quarterly Rebalance - Bloomberg
7-What do I do in bed that drives you wild? How about, what turns you off?
9- If you could have three wishes, what would they be? Why?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Nintendo has replaced the longtime voice of Peach and Toad - Polygon
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
You know that I will be 100% truthful, so ask.
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Why do only ugly women like me on Tinder? Is it because I'm an ugly man?
21~ What was the best date you ever went on? What has been the worst?
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?
Any that are a turn off?
Physicists observe a new form of magnetism for the first time - Phys.org
24~ What are your expectations in a relationship? (I know a very big question, take your time)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
92~ Everyone needs a “safe” word. What is yours?
12- What’s your favorite food? What’s your least favorite?
13- How about having a certain hair cut/style?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
HBO’s New Movie Fiercely Splits Critics & Audiences On Rotten Tomatoes - Screen Rant
Get this wrong and this could mean the end… :-) some funny, some not…
9- What’s your favorite season and why? What’s your least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Do you believe that Jesus was God on Earth?
13- What is the craziest/scariest thing you've ever done?
32- What's your greatest talent? Can I see it right now?
*** Random Questions ***
Europe cuts interest rates as Trump's tariffs loom - BBC
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
17- What’s your favorite holiday? What’s your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you like it when they show and tell you what they want?
15- What's your favorite saying? What word or phrase is your least favorite?
I would allow you to do it… What would you do to me?
Would you ever want to be woken up with oral and/or intercourse?
70~ Would/do you have/like anal sex?
31- If given a chance to be immortal, would you take it? Why?
11- List at least 5 things on your bucket list. Have you done any of them already?
Will you cheat again? How can, you be sure? Define what cheating is to you.
23- What is your dream job? What was it as a child?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
5~ When you first started having sex, was it what you thought it would be?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
38~ Share your most embarrassing sexual memory?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Any that are a turn off?
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?
Do you think this brought you closer together?
56~ Would you ever go to a strip club with your partner? Have you ever been? 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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
1- What’s your favorite animal? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
If NO, would you ever have one? Would it be with 2 men or 2 women?
28- What are some things that people do that irritate you?
19- What’s your favorite fairytale? What’s your least favorite?
1~ How old were you when you had your first kiss? Who? Care to Share?
Do you have a favorite? Is it ok if your partner does?
Model/Photographer Police/Criminal
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
2- What’s your favorite color? Do you a least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What would you say to prove to yourself that it was really you?
Would /have you ever given your partner a lap dance and Striptease?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
80~ Share your top three fantasies/desires. (Be detailed) 😊
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
29~ What are some things that turn you off? What is your biggest turn off?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you watch it? What is your favorite?
What have you learned about me that was new and/or surprising?
*** Questions About Me ***
Over time has your thoughts on sex changed?
What do you dislike about me? I asked you to be 100% honest.
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)
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
18~ Who/when was your first “crush”?
11- What's your favorite restaurant? What’s your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
53~ How much can you tell me about the one thing you are most passionate about?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
8- What are your thoughts on politics?
19~ Who/when was your first “heartbreak”?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
30~ What's something unexpected that turns you on?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Master/Slave Boss/Maid
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Does the thought excite you? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
83~ How do you feel about Porn?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
If YES, was it with 2 men or 2 women? Did you enjoy it?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Prisoner/Prison Guard Landlord/Tenant
46~ Have you ever used furniture, or other types of things to aid you while having sex?
21- What's your favorite way to spend a weekend or time off?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
How many times do you think you have “made love”?
51~ What tends to bring a smile to your face?
36~ What is your favorite time of day to have sex/make love?
39~ What are your love languages?
44~ Care to share something about yourself that no one else knows about you?
7- What if a person smells a certain way? 8- How about smoking?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
17- Have you ever done drugs? Which ones? How often?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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…
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
47~ What would be your dream job and why?
50~ How many children do you have? What are their ages?
48~ Do you have any siblings? Are you close to your family?
27- What was/ is nickname? Does it have a meaning behind it?
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Teacher/Student Stranger/One Night Stand
If you win, what will you make them do?
51~ Are you willing to play adult games with your partner?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What was the longest? What was the shortest?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
14- What's your favorite dessert? Do you a least favorite?
82~ Do you have any fantasies involving Role-Playing?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
* Give a rating for each one (0-100)
19- Do/have you smoked? What do you prefer? How often?
13~ Is there a difference between, making love, having sex, and fucking?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
49~ How many times have you been married? Why did they end?
25~ How do you feel about PDA? (Public Display of Affection)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
10- List 5 of your top pet peeves.
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Do you like the “69” position? Do you prefer to be on top or bottom?
10- What is your favorite family tradition? What’s your least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
62~ Have you used adult toys?
3- What Superhero or Superpower would you want to be/have?
6- Do you have dreams? Can you remember them? What do you usually dream about?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
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?
84~ How do you feel about reading/listening to adult stories?
3- Should Pluto still be considered a planet? 4- How about smoking?
40~ What’s the weirdest place you’ve ever had sex?
How old are you? Male or Female?
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?
34~ Do you like the lights on or off during sex?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
81~ Do you have any kinks and/or fetishes?
36- Do you play video games? What is your favorite? Do you a least favorite?
That one or two things that made you go hmmmm, OMG or wow!
52~ What are your hobbies?
5- Have you ever been hypnotized? Would you allow yourself to be?
42~ What’s your biggest regret in life?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Doctor/Nurse Stripper/Client
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Would you mind if your partner watched it? How about together vs alone?
Family Relation Age Play
Can you Deep Throat? Do you like the taste of yourself?
*** Deal Breaker Questions ***
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
22- What is your favorite childhood memory? What is your least favorite?
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,
4- For a pet, Cat, dog or other?
33- If you could visit any time period, when would you pick? Please explain why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
29- How superstitious are you?
18- How often do you drink alcohol? What is your favorite drink?
22- Do you have any birth marks? How about scars? Care to share how you got them?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
10~ How many dates are necessary before you to have sex with someone?
Nothing too Serious
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
7- What are your thoughts on religion? Is there an afterlife?
How many partners have you had oral sex with? Who? 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?
15- What bad habit do you wish you could quit? Do you have any addictions?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
92~ Have you ever had or have an STD? How many? What was it?
12- What is the weirdest thing you've ever eaten?
*** Questions about Relationships/Past ***
The Ice Breaker Questions
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How about if they talk dirty and/or call you names?
Have you ever? Care to Share?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
71~ Would you give your partner a hand or foot job? Would you receive one?
*** What’s Your Favorite…? ***
43~ Ever had your hair pulled 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?
Escort/Client Job Applicant/Hiring Manager
What is your favorite toy? Ever wanted to try a specific toy?
60~ How important is oral sex? Do you like receiving? Do you like giving?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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…
If yes, what?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
61~ How willing would you be to try new sexual positions?
26~ What side of the bed do you sleep on?
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?
67~ Do you like it when your partner moans and/or is vocal during sex?
What is your view on sex? Meaning, When/Where/ How often/
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
13- What’s your favorite drink? What’s your least favorite?
9~ How many times over your lifetime do you think you have had sex so far?
Repairman/Lonely Wife Virgin/Experienced
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
76~ Have you had a threesome? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
11~ Have you ever been caught by your parents or children or others while having sex?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Please share Did you stop?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
How well do you know me? And some of your thoughts about me
What have you learned about yourself that you did not before this?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
If you say it, I will stop, and we can talk about it when you are ready.
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
Would you allow me to clean every part of your body with my soapy hands and fingers?