What is the most interesting question you can ask to get to know someone?
11.06.2025 19:37
If you win, what will you make them do?
14- What is an embarrassing moment in your life? How about your most embarrassing?
11- What's your favorite restaurant? What’s your least favorite?
21~ What was the best date you ever went on? What has been the worst?
*** What’s Your Favorite…? ***
Would /have you ever given your partner a lap dance and Striptease?
What does K mean in Vietnamese?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
10- What is your favorite family tradition? What’s your least favorite?
Is modular building a fix for NY's housing crisis? State officials hope so. - Gothamist
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How many partners have you had oral sex with? Who? Care to Share?
17- Have you ever done drugs? Which ones? How often?
RFK Jr. looks to fast track rare disease drug approvals (updated) - Seeking Alpha
37- Do you like your name? If you could change it, what would you change it too?
Would you do it again, and would you rather 2 females or 2 males?
1- What was your first impression of me? Has it changed?
Is it legal for an employer to ask why you are taking time off from work?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What would you say to prove to yourself that it was really you?
Nintendo Switch 2 sales shatters records, most-sold console in 24-hour period - TweakTown
35- Do you like playing board or cards game? What is your favorite? 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?
Doctor/Nurse Stripper/Client
Panthers' winning formula goes missing in Stanley Cup Final Game 1 loss to Oilers - NHL.com
If yes, what?
4- For a pet, Cat, dog or other?
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…
Column | Phil Mickelson’s legacy: Helping pro golfers and diminishing pro golf - The Washington Post
47~ What would be your dream job and why?
7-What do I do in bed that drives you wild? How about, what turns you off?
I would allow you to do it… What would you do to me?
Molly Jong-Fast on Human Frailty and Unlearning Erica Jong’s Lessons - Literary Hub
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Blue Diamond to close historic midtown Sacramento plant; 600 jobs affected - Sacramento Bee
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
Family Relation Age Play
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
What caused the Democratic Party's 2024 presidential campaign to implode so horrifically?
89~ Do you like taking showers together?
26~ What side of the bed do you sleep on?
If you say it, I will stop, and we can talk about it when you are ready.
Could Trump’s ‘big beautiful bill’ kill the OFR and accidentally sabotage SOFR? - Financial Times
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
You know that I will be 100% truthful, so ask.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Subway owner buys mega-popular chicken chain in $1 billion deal - AL.com
Do you shave/trim your pubic hair? For you guys do you shave your balls?
82~ Do you have any fantasies involving Role-Playing?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
51~ What tends to bring a smile to your face?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
13- How about having a certain hair cut/style?
21- What's your favorite way to spend a weekend or time off?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
31- If given a chance to be immortal, would you take it? Why?
What is your view on sex? Meaning, When/Where/ How often/
41~ Are there moments in your past that you would want to change? Please share 3 of them.
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
*** Questions About Me ***
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
70~ Would/do you have/like anal sex?
*** Random Questions ***
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
60~ How important is oral sex? Do you like receiving? Do you like giving?
(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…)
83~ How do you feel about Porn?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
17- What’s your favorite holiday? What’s your least favorite?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Can you Deep Throat? Do you like the taste of yourself?
9- What’s your favorite season and why? What’s your least favorite?
Over time has your thoughts on sex changed?
18~ Who/when was your first “crush”?
49~ How many times have you been married? Why did they end?
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?
19- What’s your favorite fairytale? What’s your least favorite?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
19- Do/have you smoked? What do you prefer? How often?
84~ How do you feel about reading/listening to adult stories?
What do you dislike about me? I asked you to be 100% honest.
Would you ever want to be woken up with oral and/or intercourse?
42~ What’s your biggest regret in life?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What was the longest? What was the shortest?
Would you allow me to clean every part of your body with my soapy hands and fingers?
11~ Have you ever been caught by your parents or children or others while having sex?
81~ Do you have any kinks and/or fetishes?
Have you ever? 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?
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your favorite animal? Do you a least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How about if they talk dirty and/or call you names?
Any that are a turn off?
38~ Share your most embarrassing sexual memory?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
2- What’s your favorite color? Do you a least favorite?
The Ice Breaker Questions
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?
25~ How do you feel about PDA? (Public Display of Affection)
Will you cheat again? How can, you be sure? Define what cheating is to you.
Prisoner/Prison Guard Landlord/Tenant
Get this wrong and this could mean the end… :-) some funny, some not…
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?
22- Do you have any birth marks? How about scars? Care to share how you got them?
9- Is there something you’ve always wanted to ask me but you’re afraid?
28- What are some things that people do that irritate you?
36- Do you play video games? What is your favorite? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
29~ What are some things that turn you off? What is your biggest turn off?
How many times do you think you have “made love”?
23- What is your dream job? What was it as a child?
80~ Share your top three fantasies/desires. (Be detailed) 😊
That one or two things that made you go hmmmm, OMG or wow!
Model/Photographer Police/Criminal
What is your favorite position? Why?
33- If you could visit any time period, when would you pick? Please explain why?
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…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What have you learned about me that was new and/or surprising?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Would you mind if your partner watched it? How about together vs alone?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
19~ Who/when was your first “heartbreak”?
Nurse/Patient Celebrity/Fan
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
8- What are your thoughts on politics?
What have you learned about yourself that you did not before this?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
3- Should Pluto still be considered a planet? 4- How about smoking?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
13- What is the craziest/scariest thing you've ever done?
3- What Superhero or Superpower would you want to be/have?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
62~ Have you used adult toys?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
33- Beach or Mountains? Or is there another place to like better?
Do you have a favorite? Is it ok if your partner does?
51~ Are you willing to play adult games with your partner?
How old are you? Male or Female?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
27- What was/ is nickname? Does it have a meaning behind it?
50~ How many children do you have? What are their ages?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral 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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
53~ How much can you tell me about the one thing you are most passionate about?
If NO, would you ever have one? Would it be with 2 men or 2 women?
48~ Have you ever paid or been paid for sex?
*** Deal Breaker Questions ***
52~ What are your hobbies?
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,
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Please share Did you stop?
1~ How old were you when you had your first kiss? Who? Care to Share?
Nothing too Serious
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Repairman/Lonely Wife Virgin/Experienced
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
Do you like the “69” position? Do you prefer to be on top or bottom?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
34- Ever been to a concert? What was your favorite? Who would you like to see?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
67~ Do you like it when your partner moans and/or is vocal during sex?
Do you watch it? What is your favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
9~ How many times over your lifetime do you think you have had sex so far?
How well do you know me? And some of your thoughts about me
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
52~ Are you willing to make “those types” of bets with your partner?
14- What's your favorite dessert? Do you a least favorite?
Do you like it when they show and tell you what they want?
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?
12- What’s your favorite food? What’s your least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Master/Slave Boss/Maid
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
6- Do you have dreams? Can you remember them? What do you usually dream about?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Do you think this brought you closer together?
*** Questions about Relationships/Past ***
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
18- How often do you drink alcohol? What is your favorite drink?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
39~ What are your love languages?
Would you read them together?
76~ Have you had a threesome? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? 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?
Any that are a turn off?
48~ Do you have any siblings? Are you close to your family?
7- What are your thoughts on religion? Is there an afterlife?
5~ When you first started having sex, was it what you thought it would be?
If YES, was it with 2 men or 2 women? Did you enjoy it?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
22- What is your favorite childhood memory? What is your least favorite?
Teacher/Student Stranger/One Night Stand
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
10- List 5 of your top pet peeves.
* Give a rating for each one (0-100)
12- What is the weirdest thing you've ever eaten?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
7- What if a person smells a certain way? 8- How about smoking?
15- What bad habit do you wish you could quit? Do you have any addictions?
11- List at least 5 things on your bucket list. Have you done any of them already?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Escort/Client Job Applicant/Hiring Manager
49~ If you could, would you want to be the opposite sex for a day, week, or year?
3- What’s your favorite smell? Do you a least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
40~ What’s the weirdest place you’ve ever had sex?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What is your favorite toy? Ever wanted to try a specific toy?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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?
36~ What is your favorite time of day to have sex/make love?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
13- What’s your favorite drink? What’s your least favorite?
Does the thought excite you? Care to share?
5- Have you ever been hypnotized? Would you allow yourself to be?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
10~ How many dates are necessary before you to have sex with someone?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
20- What’s your favorite candy? What’s your least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
44~ Care to share something about yourself that no one else knows about you?
30~ What's something unexpected that turns you on?
32- What's your greatest talent? Can I see it right now?
34~ Do you like the lights on or off during sex?
28~ What are some things that turn on? What is your biggest turn on?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
61~ How willing would you be to try new sexual positions?