What is the most interesting question you can ask to get to know someone?
12.06.2025 08:27
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
*** Questions about Relationships/Past ***
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
81~ Do you have any kinks and/or fetishes?
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 exactly is female squirting? Is it only urine or a combination of liquids?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
*** Random Questions ***
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What are the best Jewish jokes?
Do you have a favorite? Is it ok if your partner does?
If NO, would you ever have one? Would it be with 2 men or 2 women?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
70~ Would/do you have/like anal sex?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Why do you think it is bad to allow people to self-identify as a different gender?
49~ How many times have you been married? Why did they end?
8- What's your favorite flavor of ice cream? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
How One Keto Trial Set Off a New War in the Nutrition World - WIRED
26~ What side of the bed do you sleep on?
22- What is your favorite childhood memory? What is your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Delete Every App On Your Smartphone That’s On This List - Forbes
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Please share Did you stop?
48~ Have you ever paid or been paid for sex?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
40~ What’s the weirdest place you’ve ever had sex?
92~ Have you ever had or have an STD? How many? What was it?
Blood test detects multiple cancer types through cell-free DNA - Medical Xpress
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
52~ What are your hobbies?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
What are the extra benefits of a smart TV?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Astronomers finally figured out how Pluto cools itself - Boy Genius Report
Have you ever? Care to Share?
52~ Are you willing to make “those types” of bets with your partner?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
New Webb Data Confirms ‘Crazy Idea’ About Cooling Effects of Pluto’s Haze - The Daily Galaxy
25~ How do you feel about PDA? (Public Display of Affection)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
8- What are your thoughts on politics?
How Dragonfly will support the search for life on an uninhabitable world - NASASpaceFlight.com -
80~ Share your top three fantasies/desires. (Be detailed) 😊
If yes, what?
The Ice Breaker Questions
Eight Centers Lions Could Sign to Replace Frank Ragnow - Sports Illustrated
How old are you? Male or Female?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
65~ Describe the best orgasm you’ve ever had? Care to share?
10~ How many dates are necessary before you to have sex with someone?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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?
Will you cheat again? How can, you be sure? Define what cheating is to you.
22~ What is the best pickup line anyone has ever used on you? What was the worst?
42~ What’s your biggest regret in life?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
11- List at least 5 things on your bucket list. Have you done any of them already?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
32- What's your greatest talent? Can I see it right now?
48~ Do you have any siblings? Are you close to your family?
34~ Do you like the lights on or off during sex?
62~ Have you used adult toys?
(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~ Ever been spanked during sex? Did you like it? Would you like me to do it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
82~ Do you have any fantasies involving Role-Playing?
61~ How willing would you be to try new sexual positions?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Over time has your thoughts on sex changed?
Doctor/Nurse Stripper/Client
How many times do you think you have “made love”?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
What is your view on sex? Meaning, When/Where/ How often/
Would you read them together?
21- What's your favorite way to spend a weekend or time off?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
3- Should Pluto still be considered a planet? 4- How about smoking?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Model/Photographer Police/Criminal
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7-What do I do in bed that drives you wild? How about, what turns you off?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
5~ When you first started having sex, was it what you thought it would be?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
9~ How many times over your lifetime do you think you have had sex so far?
1- What’s your favorite animal? Do you a least favorite?
Teacher/Student Stranger/One Night Stand
21~ What was the best date you ever went on? What has been the worst?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
28~ What are some things that turn on? What is your biggest turn on?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
7- What if a person smells a certain way? 8- How about smoking?
How well do you know me? And some of your thoughts about me
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
37- Do you like your name? If you could change it, what would you change it too?
33- Beach or Mountains? Or is there another place to like better?
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?
How about if they talk dirty and/or call you names?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
What was the longest? What was the shortest?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
84~ How do you feel about reading/listening to adult stories?
Nothing too Serious
If YES, was it with 2 men or 2 women? Did you enjoy it?
12- What’s your favorite food? What’s your least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Does the thought excite you? Care to share?
18~ Who/when was your first “crush”?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
60~ How important is oral sex? Do you like receiving? Do you like giving?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
1- What was your first impression of me? Has it changed?
28- What are some things that people do that irritate you?
What is your favorite toy? Ever wanted to try a specific toy?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Any that are a turn off?
83~ How do you feel about Porn?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Do you think this brought you closer together?
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?
7- What are your thoughts on religion? Is there an afterlife?
33- If you could visit any time period, when would you pick? Please explain why?
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?
You know that I will be 100% truthful, so ask.
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What have you learned about me that was new and/or surprising?
4- For a pet, Cat, dog or other?
34- Ever been to a concert? What was your favorite? Who would you like to see?
3- What Superhero or Superpower would you want to be/have?
10- What is your favorite family tradition? What’s your least favorite?
51~ What tends to bring a smile to your face?
Do you like it when they show and tell you what they want?
29~ What are some things that turn you off? What is your biggest turn off?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Nurse/Patient Celebrity/Fan
39~ What are your love languages?
9- Is there something you’ve always wanted to ask me but you’re afraid?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
47~ What would be your dream job and why?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
15- What bad habit do you wish you could quit? Do you have any addictions?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
13- What’s your favorite drink? What’s your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
9- If you could have three wishes, what would they be? Why?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What is your favorite position? Why?
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?
3- What’s your favorite smell? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
13- What is the craziest/scariest thing you've ever done?
53~ How much can you tell me about the one thing you are most passionate about?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Can you Deep Throat? Do you like the taste of yourself?
Do you like the “69” position? Do you prefer to be on top or bottom?
30~ What's something unexpected that turns you on?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
*** Questions About Me ***
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
I would allow you to do it… What would you do to me?
18- How often do you drink alcohol? What is your favorite drink?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
11- What's your favorite restaurant? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
Any that are a turn off?
13- How about having a certain hair cut/style?
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?
* Give a rating for each one (0-100)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
11~ Have you ever been caught by your parents or children or others while having sex?
Do you watch it? What is your favorite?
44~ Care to share something about yourself that no one else knows about you?
Would you mind if your partner watched it? How about together vs alone?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
17- Have you ever done drugs? Which ones? How often?
What do you dislike about me? I asked you to be 100% honest.
11- How about if they like a certain sports team? 12-How about drinking too much?
Escort/Client Job Applicant/Hiring Manager
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Would you allow me to clean every part of your body with my soapy hands and fingers?
51~ Are you willing to play adult games with your partner?
Would you ever want to be woken up with oral and/or intercourse?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
29- How superstitious are you?
Master/Slave Boss/Maid
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Would you do it again, and would you rather 2 females or 2 males?
Prisoner/Prison Guard Landlord/Tenant
36~ What is your favorite time of day to have sex/make love?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How many partners have you had oral sex with? Who? Care to Share?
Get this wrong and this could mean the end… :-) some funny, some not…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
5- Have you ever been hypnotized? Would you allow yourself to be?
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…
89~ Do you like taking showers 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?
17- What’s your favorite holiday? 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?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
If you win, what will you make them do?
That one or two things that made you go hmmmm, OMG or wow!
What have you learned about yourself that you did not before this?
*** What’s Your Favorite…? ***
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
13~ Is there a difference between, making love, having sex, and fucking?
76~ Have you had a threesome? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
27- What was/ is nickname? Does it have a meaning behind it?
14- What is an embarrassing moment in your life? How about your most embarrassing?
1~ How old were you when you had your first kiss? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
12- What is the weirdest thing you've ever eaten?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
23- What is your dream job? What was it as a child?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
10- List 5 of your top pet peeves.
50~ How many children do you have? What are their ages?
2- What’s your favorite color? Do you a least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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)
15~ Have you ever been “in love”? Who? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
What would you say to prove to yourself that it was really you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
20- What’s your favorite candy? What’s your least favorite?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
19~ Who/when was your first “heartbreak”?
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?
Family Relation Age Play
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
19- What’s your favorite fairytale? What’s your least favorite?
*** Deal Breaker Questions ***
Do you shave/trim your pubic hair? For you guys do you shave your balls?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
16~ Do you believe in “soulmates”? Have you found yours? 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…
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would /have you ever given your partner a lap dance and Striptease?
92~ Everyone needs a “safe” word. What is yours?
Repairman/Lonely Wife Virgin/Experienced