What is the most interesting question you can ask to get to know someone?
12.06.2025 06:46
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Billionaire YouTuber MrBeast ‘borrowing’ money from mom for his wedding - New York Post
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
3- What’s your favorite smell? Do you a least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Wells Fargo Stock Rises as Fed Lifts Asset Cap After 7 Years - Barron's
How many partners have you had oral sex with? Who? Care to Share?
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?
38~ Share your most embarrassing sexual memory?
Experts reveal that THIS diet can reduce heart disease risk - Times of India
22- Do you have any birth marks? How about scars? Care to share how you got them?
37- Do you like your name? If you could change it, what would you change it too?
Model/Photographer Police/Criminal
What was the worst decision you ever did?
Doctor/Nurse Stripper/Client
Nothing too Serious
29- How superstitious are you?
5 Drinks to Help You Debloat, According to Dietitians - EatingWell
Do you shave/trim your pubic hair? For you guys do you shave your balls?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Do you think this brought you closer together?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Please share Did you stop?
Teacher/Student Stranger/One Night Stand
T.J. Oshie, the Caps’ beloved ‘warrior,’ announces his NHL retirement - The Washington Post
8- What's your favorite flavor of ice cream? Do you a least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
11~ Have you ever been caught by your parents or children or others while having sex?
What are the best self-care practices to improve mental health?
14- What is an embarrassing moment in your life? How about your most embarrassing?
9- What’s your favorite season and why? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Is it wise to choose your family over your honor?
45~ How do you feel about me blindfolding you? How about blindfolding me?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Escort/Client Job Applicant/Hiring Manager
29~ What are some things that turn you off? What is your biggest turn off?
51~ What tends to bring a smile to your face?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Delta Air Lines Warns Tariffs Could Halt New Airbus Orders & Eliminate Flights - Simple Flying
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
18~ Who/when was your first “crush”?
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?
What nonsense did you hear today in India that made you laugh?
How old are you? Male or Female?
*** Random Questions ***
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
2 dead in Las Vegas Strip shooting, with suspect known but not yet arrested, police say - ABC News
If YES, was it with 2 men or 2 women? Did you enjoy it?
10- What is your favorite family tradition? What’s your least favorite?
Have you ever? Care to Share?
Sean Combs Complains to Court Sketch Artist - Newser
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
*** Questions about Relationships/Past ***
5- Have you ever been hypnotized? Would you allow yourself to be?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
13- What is the craziest/scariest thing you've ever done?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you like the “69” position? Do you prefer to be on top or bottom?
11- How about if they like a certain sports team? 12-How about drinking too much?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
28~ What are some things that turn on? What is your biggest turn on?
*** Questions About Me ***
4- For a pet, Cat, dog or other?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
83~ How do you feel about Porn?
52~ Are you willing to make “those types” of bets with your partner?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
27- What was/ is nickname? Does it have a meaning behind it?
The Ice Breaker Questions
12- What is the weirdest thing you've ever eaten?
1~ How old were you when you had your first kiss? Who? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
7- What if a person smells a certain way? 8- How about smoking?
What is your view on sex? Meaning, When/Where/ How often/
Prisoner/Prison Guard Landlord/Tenant
15~ Have you ever been “in love”? Who? Care to Share?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
70~ Would/do you have/like anal sex?
89~ Do you like taking showers together?
21- What's your favorite way to spend a weekend or time off?
What have you learned about yourself that you did not before this?
5~ When you first started having sex, was it what you thought it would be?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
28- What are some things that people do that irritate you?
If yes, what?
Master/Slave Boss/Maid
92~ Have you ever had or have an STD? How many? What was it?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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 bad habit do you wish you could quit? Do you have any addictions?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
32- What's your greatest talent? Can I see it right now?
Would /have you ever given your partner a lap dance and Striptease?
19- Do/have you smoked? What do you prefer? How often?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Any that are a turn off?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Will you cheat again? How can, you be sure? Define what cheating is to you.
26~ What side of the bed do you sleep on?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If you say it, I will stop, and we can talk about it when you are ready.
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?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
44~ Care to share something about yourself that no one else knows about you?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
13~ Is there a difference between, making love, having sex, and fucking?
3- Should Pluto still be considered a planet? 4- How about smoking?
*** Deal Breaker Questions ***
Nurse/Patient Celebrity/Fan
16~ Do you believe in “soulmates”? Have you found yours? Who? 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…)
42~ What’s your biggest regret in life?
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?
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 was the longest? What was the shortest?
19~ Who/when was your first “heartbreak”?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
*** What’s Your Favorite…? ***
80~ Share your top three fantasies/desires. (Be detailed) 😊
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
How many times do you think you have “made love”?
48~ Have you ever paid or been paid for sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
39~ What are your love languages?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
9- If you could have three wishes, what would they be? Why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Would you do it again, and would you rather 2 females or 2 males?
34~ Do you like the lights on or off during sex?
8- What are your thoughts on politics?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
92~ Everyone needs a “safe” word. What is yours?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
17- Have you ever done drugs? Which ones? How often?
33- Beach or Mountains? Or is there another place to like better?
76~ Have you had a threesome? Care to Share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
25~ How do you feel about PDA? (Public Display of Affection)
10- List 5 of your top pet peeves.
* Give a rating for each one (0-100)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Over time has your thoughts on sex changed?
14- What's your favorite dessert? 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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
84~ How do you feel about reading/listening to adult stories?
Can you Deep Throat? Do you like the taste of yourself?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
1- What was your first impression of me? Has it changed?
Would you mind if your partner watched it? How about together vs alone?
If NO, would you ever have one? Would it be with 2 men or 2 women?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your 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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you read them together?
17- What’s your favorite holiday? What’s your least favorite?
1- What’s your favorite animal? Do you a 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,
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
3- What Superhero or Superpower would you want to be/have?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
51~ Are you willing to play adult games with your partner?
7- What are your thoughts on religion? Is there an afterlife?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
62~ Have you used adult toys?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Any that are a turn off?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
30~ What's something unexpected that turns you on?
36~ What is your favorite time of day to have sex/make love?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
61~ How willing would you be to try new sexual positions?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you have a favorite? Is it ok if your partner does?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
22- What is your favorite childhood memory? What is your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Do you like it when they show and tell you what they want?
49~ How many times have you been married? Why did they end?
82~ Do you have any fantasies involving Role-Playing?
What have you learned about me that was new and/or surprising?
What is your favorite toy? Ever wanted to try a specific toy?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Do you watch it? What is your favorite?
40~ What’s the weirdest place you’ve ever had sex?
50~ How many children do you have? What are their ages?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Would you ever want to be woken up with oral and/or intercourse?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Does the thought excite you? Care to share?
9~ How many times over your lifetime do you think you have had sex so far?
13- How about having a certain hair cut/style?
10~ How many dates are necessary before you to have sex with someone?
34- Ever been to a concert? What was your favorite? Who would you like to see?
53~ How much can you tell me about the one thing you are most passionate about?
What would you say to prove to yourself that it was really you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
You know that I will be 100% truthful, so ask.
31- If given a chance to be immortal, would you take it? Why?
52~ What are your hobbies?
71~ Would you give your partner a hand or foot job? Would you receive one?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Family Relation Age Play
I would allow you to do it… What would you do to me?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
How well do you know me? And some of your thoughts about me
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
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- What’s your favorite fairytale? What’s your least favorite?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
What is your favorite position? Why?
Repairman/Lonely Wife Virgin/Experienced
What do you dislike about me? I asked you to be 100% honest.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
How about if they talk dirty and/or call you names?
33- If you could visit any time period, when would you pick? Please explain why?
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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
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…
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
23- What is your dream job? What was it as a child?
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
81~ Do you have any kinks and/or fetishes?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
48~ Do you have any siblings? Are you close to your family?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
67~ Do you like it when your partner moans and/or is vocal during sex?
18- How often do you drink alcohol? What is your favorite drink?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
11- List at least 5 things on your bucket list. Have you done any of them already?
21~ What was the best date you ever went on? What has been the worst?
If you win, what will you make them do?
47~ What would be your dream job and why?
60~ How important is oral sex? Do you like receiving? Do you like giving?
11- What's your favorite restaurant? What’s your least favorite?
12- What’s your favorite food? What’s your least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
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?