What is the most interesting question you can ask to get to know someone?
09.06.2025 02:26
*** Questions about Relationships/Past ***
*** Deal Breaker Questions ***
45~ How do you feel about me blindfolding you? How about blindfolding me?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
44~ Care to share something about yourself that no one else knows about you?
We’re About To Talk To Dolphins… But Are We Ready To Hear The Truth? - The Daily Galaxy
What is your view on sex? Meaning, When/Where/ How often/
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
Can you Deep Throat? Do you like the taste of yourself?
29- How superstitious are you?
81~ Do you have any kinks and/or fetishes?
Why do I want to give up on men?
The Ice Breaker Questions
That one or two things that made you go hmmmm, OMG or wow!
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
1- What’s your favorite animal? Do you a least favorite?
Family Relation Age Play
Prisoner/Prison Guard Landlord/Tenant
Measles case confirmed in Allegan County, officials provide locations of exposure - WWMT
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
83~ How do you feel about Porn?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
CT scan radiation and cancer risk - reassuring and alarming at the same time - Daily Kos
Would you read them together?
(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…)
Have you ever? Care to Share?
Why do philosophy of physics when you can do physics itself? - Aeon
12- What is the weirdest thing you've ever eaten?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
92~ Everyone needs a “safe” word. What is yours?
How many partners have you had oral sex with? Who? Care to Share?
Escort/Client Job Applicant/Hiring Manager
20- What’s your favorite candy? What’s your least favorite?
Do you agree with Kamala Harris that Donald Trump is dangerous?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Will you cheat again? How can, you be sure? Define what cheating is to you.
21- What's your favorite way to spend a weekend or time off?
28- What are some things that people do that irritate you?
51~ What tends to bring a smile to your face?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Mark Hamill Say Carrie Fisher Told Him to Embrace His Star Wars Fame - Variety
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
What was the longest? What was the shortest?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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,
50~ How many children do you have? What are their ages?
*** Random Questions ***
21~ What was the best date you ever went on? What has been the worst?
Would you ever want to be woken up with oral and/or intercourse?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
60~ How important is oral sex? Do you like receiving? Do you like giving?
2- What’s your favorite color? Do you a least favorite?
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
89~ Do you like taking showers together?
62~ Have you used adult toys?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
You know that I will be 100% truthful, so ask.
If you win, what will you make them do?
1~ How old were you when you had your first kiss? Who? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
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)
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Would /have you ever given your partner a lap dance and Striptease?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
How many times do you think you have “made love”?
9- Is there something you’ve always wanted to ask me but you’re afraid?
13- What is the craziest/scariest thing you've ever done?
13- What’s your favorite drink? What’s your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
52~ Are you willing to make “those types” of bets with your partner?
28~ What are some things that turn on? What is your biggest turn on?
Do you watch it? What is your favorite?
10- List 5 of your top pet peeves.
Please share Did you stop?
4- For a pet, Cat, dog or other?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
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…
22- Do you have any birth marks? How about scars? Care to share how you got them?
36- Do you play video games? What is your favorite? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
36~ What is your favorite time of day to have sex/make love?
26~ What side of the bed do you sleep on?
9- If you could have three wishes, what would they be? Why?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
17- Have you ever done drugs? Which ones? How often?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
52~ What are your hobbies?
42~ What’s your biggest regret in life?
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?
Does the thought excite you? Care to share?
11- What's your favorite restaurant? What’s your least favorite?
Nothing too Serious
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…
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
7- What if a person smells a certain way? 8- How about smoking?
Over time has your thoughts on sex changed?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
14- What is an embarrassing moment in your life? How about your most embarrassing?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
38~ Share your most embarrassing sexual memory?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Would you mind if your partner watched it? How about together vs alone?
11- List at least 5 things on your bucket list. Have you done any of them already?
70~ Would/do you have/like anal sex?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Nurse/Patient Celebrity/Fan
12- What’s your favorite food? What’s your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
*** Questions About Me ***
18~ Who/when was your first “crush”?
65~ Describe the best orgasm you’ve ever had? Care to share?
61~ How willing would you be to try new sexual positions?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Teacher/Student Stranger/One Night Stand
5- Have you ever been hypnotized? Would you allow yourself to be?
5~ When you first started having sex, was it what you thought it would be?
Do you think this brought you closer together?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Any that are a turn off?
33- If you could visit any time period, when would you pick? Please explain why?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
14- What's your favorite dessert? 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?
3- Should Pluto still be considered a planet? 4- How about smoking?
9- What’s your favorite season and why? What’s your least favorite?
34~ Do you like the lights on or off during sex?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
33- Beach or Mountains? Or is there another place to like better?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Any that are a turn off?
84~ How do you feel about reading/listening to adult stories?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
7- What are your thoughts on religion? Is there an afterlife?
19~ Who/when was your first “heartbreak”?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
15- What's your favorite saying? What word or phrase is your least favorite?
48~ Have you ever paid or been paid for sex?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
67~ Do you like it when your partner moans and/or is vocal during sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If NO, would you ever have one? Would it be with 2 men or 2 women?
If yes, what?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
51~ Are you willing to play adult games with your partner?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
71~ Would you give your partner a hand or foot job? Would you receive one?
How well do you know me? And some of your thoughts about me
Do you like it when they show and tell you what they want?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
19- Do/have you smoked? What do you prefer? How often?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Model/Photographer Police/Criminal
Master/Slave Boss/Maid
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
46~ Have you ever used furniture, or other types of things to aid you while having sex?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
39~ What are your love languages?
76~ Have you had a threesome? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
49~ How many times have you been married? Why did they end?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
27- What was/ is nickname? Does it have a meaning behind it?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
3- What Superhero or Superpower would you want to be/have?
What have you learned about yourself that you did not before this?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
10- What is your favorite family tradition? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
1- What was your first impression of me? Has it changed?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
9~ How many times over your lifetime do you think you have had sex so far?
How about if they talk dirty and/or call you names?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
8- What are your thoughts on politics?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
What have you learned about me that was new and/or surprising?
92~ Have you ever had or have an STD? How many? What was it?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
11~ Have you ever been caught by your parents or children or others while having sex?
29~ What are some things that turn you off? What is your biggest turn off?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
32- What's your greatest talent? Can I see it right now?
30~ What's something unexpected that turns you on?
Would you do it again, and would you rather 2 females or 2 males?
*** What’s Your Favorite…? ***
I would allow you to do it… What would you do to me?
Repairman/Lonely Wife Virgin/Experienced
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
8- What's your favorite flavor of ice cream? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
15~ Have you ever been “in love”? Who? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
What would you say to prove to yourself that it was really you?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
23- What is your dream job? What was it as a child?
19- What’s your favorite fairytale? What’s your least favorite?
82~ Do you have any fantasies involving Role-Playing?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
37- Do you like your name? If you could change it, what would you change it too?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
56~ Would you ever go to a strip club with your partner? Have you ever been? 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?
* Give a rating for each one (0-100)
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?
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?
17- What’s your favorite holiday? What’s your least favorite?
What is your favorite position? Why?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
How old are you? Male or Female?
Get this wrong and this could mean the end… :-) some funny, some not…
34- Ever been to a concert? What was your favorite? Who would you like to see?
31- If given a chance to be immortal, would you take it? Why?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
What is your favorite toy? Ever wanted to try a specific toy?
If YES, was it with 2 men or 2 women? Did you enjoy it?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
13- How about having a certain hair cut/style?
48~ Do you have any siblings? Are you close to your family?
18- How often do you drink alcohol? What is your favorite drink?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
15- What bad habit do you wish you could quit? Do you have any addictions?
47~ What would be your dream job and why?
Doctor/Nurse Stripper/Client
53~ How much can you tell me about the one thing you are most passionate about?
22- What is your favorite childhood memory? What is your least favorite?