What is the most interesting question you can ask to get to know someone?
Last Updated: 25.06.2025 01:16
Would you read them together?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
The Ozempic era is forcing wellness retreats for the elite to change - The Washington Post
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
29- How superstitious are you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
How do you respond to "I don't like you anymore"?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How do organic ready-to-eat meals compare to conventional ones?
44~ Care to share something about yourself that no one else knows about 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?
21~ What was the best date you ever went on? What has been the worst?
Meta in Talks for Scale AI Investment That Could Top $10 Billion - Bloomberg
81~ Do you have any kinks and/or fetishes?
Master/Slave Boss/Maid
8- What's your favorite flavor of ice cream? Do you a least favorite?
Apple iPhone 17 Series Will Showcase ‘Design Revamp,’ New Report Claims - Forbes
18- What’s your favorite way to relax after a long day? What’s your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
9~ How many times over your lifetime do you think you have had sex so far?
Any that are a turn off?
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?
60~ How important is oral sex? Do you like receiving? Do you like giving?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Is it safe to say that China is at least 30 years ahead of India?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How to protect yourself from wildfire smoke and poor air quality - The Washington Post
28- What are some things that people do that irritate you?
84~ How do you feel about reading/listening to adult stories?
Would you allow me to clean every part of your body with my soapy hands and fingers?
By skipping offseason workouts, Lamar Jackson forfeits another $750,000 - NBC Sports
3- What was the most surprising thing you’ve learned about me throughout our relationship?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Get this wrong and this could mean the end… :-) some funny, some not…
Why does Boko Haram attack its own Muslims?
Any that are a turn off?
I would allow you to do it… What would you do to me?
Family Relation Age Play
New Webb Data Confirms ‘Crazy Idea’ About Cooling Effects of Pluto’s Haze - The Daily Galaxy
61~ How willing would you be to try new sexual positions?
17- What’s your favorite holiday? What’s your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
62~ Have you used adult toys?
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…
Teacher/Student Stranger/One Night Stand
F1's Canadian GP will clash with the Indy 500 every five years - Motorsport.com
Nurse/Patient Celebrity/Fan
47~ What would be your dream job and why?
5- Have you ever been hypnotized? Would you allow yourself to be?
What are the most trending skin hydrating products of 2025?
*** What’s Your Favorite…? ***
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Will you cheat again? How can, you be sure? Define what cheating is to you.
51~ Are you willing to play adult games with your partner?
71~ Would you give your partner a hand or foot job? Would you receive one?
53~ How much can you tell me about the one thing you are most passionate about?
20- What’s your favorite candy? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
42~ What’s your biggest regret in life?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Have you ever? Care to Share?
11- What's your favorite restaurant? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Prisoner/Prison Guard Landlord/Tenant
22- What is your favorite childhood memory? What is your least favorite?
Escort/Client Job Applicant/Hiring Manager
25~ How do you feel about PDA? (Public Display of Affection)
30~ What's something unexpected that turns you on?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
38~ Share your most embarrassing sexual memory?
What is your view on sex? Meaning, When/Where/ How often/
82~ Do you have any fantasies involving Role-Playing?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
11- List at least 5 things on your bucket list. Have you done any of them already?
Would you do it again, and would you rather 2 females or 2 males?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
23- What is your dream job? What was it as a child?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
14- What's your favorite dessert? Do you a least favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
11- How about if they like a certain sports team? 12-How about drinking too much?
33- Beach or Mountains? Or is there another place to like better?
*** Questions about Relationships/Past ***
You know that I will be 100% truthful, so ask.
15- What's your favorite saying? What word or phrase is your least favorite?
What do you dislike about me? I asked you to be 100% honest.
If you win, what will you make them do?
92~ Have you ever had or have an STD? How many? What was it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
How many times do you think you have “made love”?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
13- How about having a certain hair cut/style?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
12- What is the weirdest thing you've ever eaten?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Does the thought excite you? Care to share?
Nothing too Serious
19~ Who/when was your first “heartbreak”?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Can you Deep Throat? Do you like the taste of yourself?
40~ What’s the weirdest place you’ve ever had sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
1- What was your first impression of me? Has it changed?
If you say it, I will stop, and we can talk about it when you are ready.
34~ Do you like the lights on or off during sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
9- What’s your favorite season and why? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Doctor/Nurse Stripper/Client
49~ How many times have you been married? Why did they end?
* Give a rating for each one (0-100)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
48~ Do you have any siblings? Are you close to your family?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
33- If you could visit any time period, when would you pick? Please explain why?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
36~ What is your favorite time of day to have sex/make love?
27- What was/ is nickname? Does it have a meaning behind it?
11~ Have you ever been caught by your parents or children or others while having sex?
10- List 5 of your top pet peeves.
39~ What are your love languages?
Would /have you ever given your partner a lap dance and Striptease?
How about if they talk dirty and/or call you names?
37- Do you like your name? If you could change it, what would you change it too?
3- Should Pluto still be considered a planet? 4- How about smoking?
7- What are your thoughts on religion? Is there an afterlife?
22- Do you have any birth marks? How about scars? Care to share how you got them?
(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…)
If YES, was it with 2 men or 2 women? Did you enjoy it?
What have you learned about me that was new and/or surprising?
28~ What are some things that turn on? What is your biggest turn on?
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?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
What is your favorite position? Why?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you have a favorite? Is it ok if your partner does?
4- For a pet, Cat, dog or other?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
10- What is your favorite family tradition? What’s your least favorite?
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?
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?
13- What’s your favorite drink? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
36- Do you play video games? What is your favorite? Do you a least favorite?
Over time has your thoughts on sex changed?
Do you like it when they show and tell you what they want?
17- Have you ever done drugs? Which ones? How often?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
18- How often do you drink alcohol? What is your favorite drink?
70~ Would/do you have/like anal sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
65~ Describe the best orgasm you’ve ever had? Care to share?
32- What's your greatest talent? Can I see it right now?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
9- If you could have three wishes, what would they be? Why?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Would you mind if your partner watched it? How about together vs alone?
That one or two things that made you go hmmmm, OMG or wow!
80~ Share your top three fantasies/desires. (Be detailed) 😊
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
29~ What are some things that turn you off? What is your biggest turn off?
31- If given a chance to be immortal, would you take it? Why?
The Ice Breaker Questions
22~ What is the best pickup line anyone has ever used on you? What was the worst?
18~ Who/when was your first “crush”?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
15~ Have you ever been “in love”? Who? 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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
5~ When you first started having sex, was it what you thought it would be?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
What would you say to prove to yourself that it was really you?
52~ Are you willing to make “those types” of bets with your partner?
Repairman/Lonely Wife Virgin/Experienced
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?
13- What is the craziest/scariest thing you've ever done?
Model/Photographer Police/Criminal
50~ How many children do you have? What are their ages?
45~ How do you feel about me blindfolding you? How about blindfolding me?
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,
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
26~ What side of the bed do you sleep on?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
12- What’s your favorite food? What’s your least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
*** Deal Breaker Questions ***
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
51~ What tends to bring a smile to your face?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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)
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
If yes, what?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
83~ How do you feel about Porn?
How many partners have you had oral sex with? Who? Care to Share?
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?
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…
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
2- What’s your favorite color? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
*** Random Questions ***
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What was the longest? What was the shortest?
89~ Do you like taking showers together?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
52~ What are your hobbies?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Do you think this brought you closer together?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
14- What is an embarrassing moment in your life? How about your most embarrassing?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
1- What’s your favorite animal? Do you a least favorite?
How old are you? Male or Female?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
92~ Everyone needs a “safe” word. What is yours?
21- What's your favorite way to spend a weekend or time off?
Do you watch it? What is your favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
10~ How many dates are necessary before you to have sex with someone?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
8- What are your thoughts on politics?
Please share Did you stop?
3- What’s your favorite smell? Do you a 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?
19- Do/have you smoked? What do you prefer? How often?
76~ Have you had a threesome? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
7- What if a person smells a certain way? 8- How about smoking?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would you ever want to be woken up with oral and/or intercourse?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
*** Questions About Me ***