What is the most interesting question you can ask to get to know someone?
12.06.2025 04:34
*** Questions About Me ***
10- List 5 of your top pet peeves.
1- What was your first impression of me? Has it changed?
Everything Apple Announced at WWDC 2025 - WIRED
Can you Deep Throat? Do you like the taste of yourself?
33- Beach or Mountains? Or is there another place to like better?
Do you like it when they show and tell you what they want?
Walkoff caps ‘unreal 24 hours’ for Mariners’ Cole Young - Seattle Sports
Will you cheat again? How can, you be sure? Define what cheating is to you.
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Have you ever regretted not hitting on a older women?
81~ Do you have any kinks and/or fetishes?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
13- What’s your favorite drink? What’s your least favorite?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
36~ What is your favorite time of day to have sex/make love?
10~ How many dates are necessary before you to have sex with someone?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
8- What are your thoughts on politics?
If NO, would you ever have one? Would it be with 2 men or 2 women?
48~ Do you have any siblings? Are you close to your family?
If YES, was it with 2 men or 2 women? Did you enjoy it?
How many partners have you had oral sex with? Who? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
21- What's your favorite way to spend a weekend or time off?
Japanese culture: Is it true adult adoption is common in Japan?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Any that are a turn off?
What have you learned about me that was new and/or surprising?
Utah’s quiet measles case: what happened and why officials stayed silent - KSLTV.com
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
18- How often do you drink alcohol? What is your favorite drink?
33- If you could visit any time period, when would you pick? Please explain why?
Why do companies cull employees during financial downturns without saying so?
Would you read them together?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
How did you get to be a leftist?
48~ Have you ever paid or been paid for sex?
Would /have you ever given your partner a lap dance and Striptease?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
19- Do/have you smoked? What do you prefer? How often?
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)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you watch it? What is your favorite?
Any that are a turn off?
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?
44~ Care to share something about yourself that no one else knows about you?
30~ What's something unexpected that turns you on?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
47~ What would be your dream job and why?
84~ How do you feel about reading/listening to adult stories?
15- What bad habit do you wish you could quit? Do you have any addictions?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
51~ Are you willing to play adult games with your partner?
65~ Describe the best orgasm you’ve ever had? Care to share?
Family Relation Age Play
11~ Have you ever been caught by your parents or children or others while having sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Do you think this brought you closer together?
11- How about if they like a certain sports team? 12-How about drinking too much?
29- How superstitious are you?
*** Questions about Relationships/Past ***
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
17- Have you ever done drugs? Which ones? How often?
Model/Photographer Police/Criminal
71~ Would you give your partner a hand or foot job? Would you receive one?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
38~ Share your most embarrassing sexual memory?
80~ Share your top three fantasies/desires. (Be detailed) 😊
14- What is an embarrassing moment in your life? How about your most embarrassing?
28- What are some things that people do that irritate you?
2- What’s your favorite color? Do you a least favorite?
22- Do you have any birth marks? How about scars? Care to share how you got them?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
What is your view on sex? Meaning, When/Where/ How often/
32- What's your greatest talent? Can I see it right now?
What have you learned about yourself that you did not before this?
12- What’s your favorite food? What’s your least favorite?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Prisoner/Prison Guard Landlord/Tenant
3- What’s your favorite smell? Do you a least favorite?
49~ How many times have you been married? Why did they end?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
21~ What was the best date you ever went on? What has been the worst?
62~ Have you used adult toys?
Nothing too Serious
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
23- What is your dream job? What was it as a child?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
13- How about having a certain hair cut/style?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
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~ When you first started having sex, was it what you thought it would be?
What do you dislike about me? I asked you to be 100% honest.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
13- What is the craziest/scariest thing you've ever done?
31- If given a chance to be immortal, would you take it? Why?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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,
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
11- List at least 5 things on your bucket list. Have you done any of them already?
11- What's your favorite restaurant? What’s your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
27- What was/ is nickname? Does it have a meaning behind it?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
What is your favorite toy? Ever wanted to try a specific toy?
12- What is the weirdest thing you've ever eaten?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
82~ Do you have any fantasies involving Role-Playing?
20- What’s your favorite candy? What’s your least favorite?
*** Random Questions ***
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
*** Deal Breaker Questions ***
What was the longest? What was the shortest?
Repairman/Lonely Wife Virgin/Experienced
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…
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Teacher/Student Stranger/One Night Stand
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
15- What's your favorite saying? What word or phrase is your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
1~ How old were you when you had your first kiss? Who? Care to Share?
Over time has your thoughts on sex changed?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
10- What is your favorite family tradition? What’s your least favorite?
50~ How many children do you have? What are their ages?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
92~ Have you ever had or have an STD? How many? What was it?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
29~ What are some things that turn you off? What is your biggest turn off?
83~ How do you feel about Porn?
How old are you? Male or Female?
You know that I will be 100% truthful, so ask.
76~ Have you had a threesome? Care to Share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
36- Do you play video games? What is your favorite? Do you a least favorite?
Do you have a favorite? Is it ok if your partner does?
39~ What are your love languages?
25~ How do you feel about PDA? (Public Display of Affection)
8- What's your favorite flavor of ice cream? Do you a least favorite?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
52~ Are you willing to make “those types” of bets with your partner?
3- Should Pluto still be considered a planet? 4- How about smoking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
9~ How many times over your lifetime do you think you have had sex so far?
22- What is your favorite childhood memory? What is your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
7-What do I do in bed that drives you wild? How about, what turns you off?
92~ Everyone needs a “safe” word. What is yours?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
89~ Do you like taking showers together?
Doctor/Nurse Stripper/Client
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? 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?
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
26~ What side of the bed do you sleep on?
How about if they talk dirty and/or call you names?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Does the thought excite you? Care to share?
34~ Do you like the lights on or off during sex?
Escort/Client Job Applicant/Hiring Manager
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Get this wrong and this could mean the end… :-) some funny, some not…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
The Ice Breaker Questions
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Do you like the “69” position? Do you prefer to be on top or bottom?
Would you ever want to be woken up with oral and/or intercourse?
18~ Who/when was your first “crush”?
40~ What’s the weirdest place you’ve ever had sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
That one or two things that made you go hmmmm, OMG or wow!
35- Do you like playing board or cards game? What is your favorite? 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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
42~ What’s your biggest regret in life?
(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…)
If you win, what will you make them do?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
61~ How willing would you be to try new sexual positions?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
If you say it, I will stop, and we can talk about it when you are ready.
17- What’s your favorite holiday? What’s your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
3- What Superhero or Superpower would you want to be/have?
5- Have you ever been hypnotized? Would you allow yourself to be?
52~ What are your hobbies?
9- Is there something you’ve always wanted to ask me but you’re afraid?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
6- Do you have dreams? Can you remember them? What do you usually dream about?
* Give a rating for each one (0-100)
37- Do you like your name? If you could change it, what would you change it too?
9- If you could have three wishes, what would they be? Why?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Please share Did you stop?
1- What’s your favorite animal? Do you a least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Nurse/Patient Celebrity/Fan
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
14- What's your favorite dessert? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
19- What’s your favorite fairytale? What’s your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Master/Slave Boss/Maid
28~ What are some things that turn on? What is your biggest turn on?
19~ Who/when was your first “heartbreak”?
51~ What tends to bring a smile to your face?
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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
I would allow you to do it… What would you do to me?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If yes, what?
70~ Would/do you have/like anal sex?
What is your favorite position? Why?
13~ Is there a difference between, making love, having sex, and fucking?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Have you ever? Care to Share?
*** What’s Your Favorite…? ***
4- For a pet, Cat, dog or other?
What would you say to prove to yourself that it was really you?
60~ How important is oral sex? Do you like receiving? Do you like giving?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
How many times do you think you have “made love”?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?