What is the most interesting question you can ask to get to know someone?
Last Updated: 03.07.2025 01:31
Model/Photographer Police/Criminal
What have you learned about me that was new and/or surprising?
Get this wrong and this could mean the end… :-) some funny, some not…
Earth's atmosphere hasn't had this much CO2 in millions of years - NBC News
35- Do you like playing board or cards game? What is your favorite? 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,
42~ What’s your biggest regret in life?
SpaceX launches 23 Starlink satellites on Falcon 9 rocket from Cape Canaveral - Spaceflight Now
Would you mind if your partner watched it? How about together vs alone?
67~ Do you like it when your partner moans and/or is vocal during sex?
11- What's your favorite restaurant? What’s your least favorite?
‘Echo Valley’ Is the Trashiest A-List Lifetime Movie You’ve Ever Seen - rollingstone.com
11~ Have you ever been caught by your parents or children or others while having sex?
What is your favorite position? Why?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Acting NASA Administrator Janet Petro June 6, 2025 - NASA Watch
11- How about if they like a certain sports team? 12-How about drinking too much?
If you win, what will you make them do?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
29~ What are some things that turn you off? What is your biggest turn off?
9- If you could have three wishes, what would they be? Why?
Weight stigma isn’t just cruel — it makes losing weight harder - CNN
30~ What's something unexpected that turns you on?
I would allow you to do it… What would you do to me?
The Ice Breaker Questions
Sovereignty Wins 2025 Belmont Stakes, Beats Journalism in Final Triple Crown Leg - Bleacher Report
Would you ever want to be woken up with oral and/or intercourse?
Would /have you ever given your partner a lap dance and Striptease?
92~ Everyone needs a “safe” word. What is yours?
MLB Power Rankings: Phillies take charge in NL East, Junior Caminero leads Rays’ rise - NBC Sports
17- Have you ever done drugs? Which ones? How often?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Michaels acquires Joann’s intellectual property, private label brands - WSB-TV
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
51~ What tends to bring a smile to your face?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
ChatGPT Just Got 'Absolutely Wrecked' at Chess, Losing to a 1970s-Era Atari 2600 - CNET
How well do you know me? And some of your thoughts about me
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
44~ Care to share something about yourself that no one else knows about you?
84~ How do you feel about reading/listening to adult stories?
Over time has your thoughts on sex changed?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
What do you dislike about me? I asked you to be 100% honest.
33- Beach or Mountains? Or is there another place to like better?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Main Card Results | UFC 316: Dvalishvili vs O'Malley 2 - UFC.com
12- What’s your favorite food? What’s your least favorite?
*** Deal Breaker Questions ***
52~ What are your hobbies?
Which is a good budget sunscreen for my oily skin?
25~ How do you feel about PDA? (Public Display of Affection)
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
34~ Do you like the lights on or off during sex?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
37- Do you like your name? If you could change it, what would you change it too?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
62~ Have you used adult toys?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
*** Random Questions ***
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
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?
10- List 5 of your top pet peeves.
80~ Share your top three fantasies/desires. (Be detailed) 😊
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
36- Do you play video games? What is your favorite? Do you a least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
15~ Have you ever been “in love”? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
5- Have you ever been hypnotized? Would you allow yourself to be?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
76~ Have you had a threesome? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Any that are a turn off?
If YES, was it with 2 men or 2 women? Did you enjoy it?
1- What was your first impression of me? Has it changed?
Would you read them together?
Escort/Client Job Applicant/Hiring Manager
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
21- What's your favorite way to spend a weekend or time off?
What was the longest? What was the shortest?
13- What’s your favorite drink? What’s your least favorite?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
9~ How many times over your lifetime do you think you have had sex so far?
Would you do it again, and would you rather 2 females or 2 males?
13~ Is there a difference between, making love, having sex, and fucking?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
53~ How much can you tell me about the one thing you are most passionate about?
2- What’s your favorite color? 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?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
71~ Would you give your partner a hand or foot job? Would you receive one?
*** Questions about Relationships/Past ***
12- What is the weirdest thing you've ever eaten?
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
3- Should Pluto still be considered a planet? 4- How about smoking?
* Give a rating for each one (0-100)
19- Do/have you smoked? What do you prefer? How often?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Will you kiss after your partner has gone down on you? Swallow or spit semen?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
7- What are your thoughts on religion? Is there an afterlife?
18- How often do you drink alcohol? What is your favorite drink?
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?
If yes, what?
That one or two things that made you go hmmmm, OMG or wow!
18- What’s your favorite way to relax after a long day? What’s your least favorite?
51~ Are you willing to play adult games with your partner?
29- How superstitious are you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
7-What do I do in bed that drives you wild? How about, what turns you off?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Please share Did you stop?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Prisoner/Prison Guard Landlord/Tenant
Do you have a favorite? Is it ok if your partner does?
31- If given a chance to be immortal, would you take it? Why?
20- What’s your favorite candy? What’s your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
14- What's your favorite dessert? Do you a least favorite?
Nurse/Patient Celebrity/Fan
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
70~ Would/do you have/like anal sex?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
8- What are your thoughts on politics?
Do you like it when they show and tell you what they want?
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…
13- What is the craziest/scariest thing you've ever done?
(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…)
10- What is your favorite family tradition? What’s your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Repairman/Lonely Wife Virgin/Experienced
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
60~ How important is oral sex? Do you like receiving? Do you like giving?
61~ How willing would you be to try new sexual positions?
What have you learned about yourself that you did not before this?
48~ Do you have any siblings? Are you close to your family?
Does the thought excite you? Care to share?
Do you think this brought you closer together?
Master/Slave Boss/Maid
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
83~ How do you feel about Porn?
81~ Do you have any kinks and/or fetishes?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How old are you? Male or Female?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
23- What is your dream job? What was it as a child?
5- What do I do outside the bedroom that turns you on? How about, what turns you 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?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
17- What’s your favorite holiday? 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…
40~ What’s the weirdest place you’ve ever had sex?
33- If you could visit any time period, when would you pick? Please explain why?
28~ What are some things that turn on? What is your biggest turn on?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Family Relation Age Play
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
3- What’s your favorite smell? Do you a least favorite?
4- For a pet, Cat, dog or other?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
16~ Do you believe in “soulmates”? Have you found yours? Who? 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?
19~ Who/when was your first “heartbreak”?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
22- What is your favorite childhood memory? What is your least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
49~ How many times have you been married? Why did they end?
Do you watch it? What is your favorite?
*** What’s Your Favorite…? ***
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
82~ Do you have any fantasies involving Role-Playing?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Nothing too Serious
89~ Do you like taking showers together?
19- What’s your favorite fairytale? What’s your least favorite?
38~ Share your most embarrassing sexual memory?
52~ Are you willing to make “those types” of bets with your partner?
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?
39~ What are your love languages?
Do you like the “69” position? Do you prefer to be on top or bottom?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
27- What was/ is nickname? Does it have a meaning behind it?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
15- What's your favorite saying? What word or phrase is your least favorite?
13- How about having a certain hair cut/style?
34- Ever been to a concert? What was your favorite? Who would you like to see?
15- What bad habit do you wish you could quit? Do you have any addictions?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
36~ What is your favorite time of day to have sex/make love?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What would you say to prove to yourself that it was really you?
*** Questions About Me ***
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.
21~ What was the best date you ever went on? What has been the worst?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
If you say it, I will stop, and we can talk about it when you are ready.
6- Do you have dreams? Can you remember them? What do you usually dream about?
What is your view on sex? Meaning, When/Where/ How often/
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Have you ever? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
64~ When was your very first orgasm? When was your first from having sex? Care to share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
Any that are a turn off?
What is your favorite toy? Ever wanted to try a specific toy?
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?
28- What are some things that people do that irritate you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
26~ What side of the bed do you sleep on?
Teacher/Student Stranger/One Night Stand
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)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Doctor/Nurse Stripper/Client
Can you Deep Throat? Do you like the taste of yourself?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
3- What Superhero or Superpower would you want to be/have?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
32- What's your greatest talent? Can I see it right now?
How about if they talk dirty and/or call you names?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
How many partners have you had oral sex with? Who? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
How many times do you think you have “made love”?
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…
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
18~ Who/when was your first “crush”?
You know that I will be 100% truthful, so ask.
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
50~ How many children do you have? What are their ages?
5~ When you first started having sex, was it what you thought it would be?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
47~ What would be your dream job and why?