What is the most interesting question you can ask to get to know someone?
13.06.2025 07:40
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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~ Everyone needs a “safe” word. What is yours?
I am 13 and I am planning to run away. What should I do to succeed?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Why am I so jealous towards couples? Why am I tired of being single and feel my life is over?
30~ What's something unexpected that turns you on?
81~ Do you have any kinks and/or fetishes?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What are the most shocking facts about the Bollywood industry?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
23- What is your dream job? What was it as a child?
52~ Are you willing to make “those types” of bets with your partner?
Is homosexuality an excommunicable offense in Christianity?
What have you learned about yourself that you did not before this?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
32- What's your greatest talent? Can I see it right now?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Get this wrong and this could mean the end… :-) some funny, some not…
Do you usually wear your panties over or under your pantyhose?
What is your favorite toy? Ever wanted to try a specific toy?
Model/Photographer Police/Criminal
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What does pompano fish taste like?
Repairman/Lonely Wife Virgin/Experienced
7- What are your thoughts on religion? Is there an afterlife?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
What are your funniest "lost in translation" moments if you grew up speaking more than one language?
Prisoner/Prison Guard Landlord/Tenant
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Would you read them together?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
I would allow you to do it… What would you do to me?
Why do Democrats look like snowflakes and Republicans look like Vikings?
9- What’s your favorite season and why? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Have you ever had your crush reject you, and then later you all dated and married?
Any that are a turn off?
51~ What tends to bring a smile to your face?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Would you date/marry a guy younger than you? If no, why not?
20- What’s your favorite candy? What’s your least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
14- What is an embarrassing moment in your life? How about your most embarrassing?
*** Deal Breaker Questions ***
4- For a pet, Cat, dog or other?
Why has Biden pulled ahead in battleground states and is now projected to win the 2024 presidency?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Nothing too Serious
Have you ever had sex with your female cousin? How did it start?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
The Ice Breaker Questions
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
15- What bad habit do you wish you could quit? Do you have any addictions?
That one or two things that made you go hmmmm, OMG or wow!
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
18- What’s your favorite way to relax after a long day? What’s your least favorite?
31- If given a chance to be immortal, would you take it? Why?
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?
84~ How do you feel about reading/listening to adult stories?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
If yes, what?
28- What are some things that people do that irritate you?
65~ Describe the best orgasm you’ve ever had? Care to share?
Family Relation Age Play
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
How many partners have you had oral sex with? Who? Care to Share?
18~ Who/when was your first “crush”?
1- What’s your favorite animal? Do you a least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
41~ Are there moments in your past that you would want to change? Please share 3 of them.
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Do you like it when they show and tell you what they want?
52~ What are your hobbies?
If you say it, I will stop, and we can talk about it when you are ready.
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
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,
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
39~ What are your love languages?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
36~ What is your favorite time of day to have sex/make love?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
21~ What was the best date you ever went on? What has been the worst?
67~ Do you like it when your partner moans and/or is vocal during sex?
7-What do I do in bed that drives you wild? How about, what turns you off?
Would you ever want to be woken up with oral and/or intercourse?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Would you do it again, and would you rather 2 females or 2 males?
Escort/Client Job Applicant/Hiring Manager
10- What is your favorite family tradition? What’s your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
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?
You know that I will be 100% truthful, so ask.
51~ Are you willing to play adult games with your partner?
If NO, would you ever have one? Would it be with 2 men or 2 women?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Teacher/Student Stranger/One Night Stand
34~ Do you like the lights on or off during sex?
70~ Would/do you have/like anal sex?
Any that are a turn off?
Doctor/Nurse Stripper/Client
3- What’s your favorite smell? Do you a least favorite?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
9- If you could have three wishes, what would they be? Why?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
45~ How do you feel about me blindfolding you? How about blindfolding me?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
61~ How willing would you be to try new sexual positions?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
28~ What are some things that turn on? What is your biggest turn on?
If YES, was it with 2 men or 2 women? Did you enjoy it?
18- How often do you drink alcohol? What is your favorite drink?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
How many times do you think you have “made love”?
* Give a rating for each one (0-100)
Do you think this brought you closer together?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
47~ What would be your dream job and why?
10- List 5 of your top pet peeves.
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
*** What’s Your Favorite…? ***
What was the longest? What was the shortest?
11- What's your favorite restaurant? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What do you dislike about me? I asked you to be 100% honest.
76~ Have you had a threesome? Care to Share?
8- What are your thoughts on politics?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
1~ How old were you when you had your first kiss? Who? Care to Share?
29- How superstitious are you?
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?
42~ What’s your biggest regret in life?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
19- Do/have you smoked? What do you prefer? How often?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What is your favorite position? Why?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
Master/Slave Boss/Maid
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
89~ Do you like taking showers together?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
2- What’s your favorite color? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
How about if they talk dirty and/or call you names?
36- Do you play video games? What is your favorite? Do you a least favorite?
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…
44~ Care to share something about yourself that no one else knows about you?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Does the thought excite you? Care to share?
7- What if a person smells a certain way? 8- How about smoking?
Please share Did you stop?
50~ How many children do you have? What are their ages?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
40~ What’s the weirdest place you’ve ever had sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
71~ Would you give your partner a hand or foot job? Would you receive one?
17- Have you ever done drugs? Which ones? How often?
83~ How do you feel about Porn?
82~ Do you have any fantasies involving Role-Playing?
6- Do you have dreams? Can you remember them? What do you usually dream about?
21- What's your favorite way to spend a weekend or time off?
33- If you could visit any time period, when would you pick? Please explain why?
How old are you? Male or Female?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
8- What's your favorite flavor of ice cream? Do you a least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
*** Random Questions ***
37- Do you like your name? If you could change it, what would you change it too?
13- What’s your favorite drink? What’s your least favorite?
14- What's your favorite dessert? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
9~ How many times over your lifetime do you think you have had sex so far?
What have you learned about me that was new and/or surprising?
17- What’s your favorite holiday? What’s your least favorite?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Can you Deep Throat? Do you like the taste of yourself?
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)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
62~ Have you used adult toys?
13- What is the craziest/scariest thing you've ever done?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Would you mind if your partner watched it? How about together vs alone?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
27- What was/ is nickname? Does it have a meaning behind it?
26~ What side of the bed do you sleep on?
10~ How many dates are necessary before you to have sex with someone?
11- How about if they like a certain sports team? 12-How about drinking too much?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
11- List at least 5 things on your bucket list. Have you done any of them already?
Over time has your thoughts on sex changed?
Nurse/Patient Celebrity/Fan
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
What would you say to prove to yourself that it was really you?
12- What’s your favorite food? What’s your least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
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?
49~ How many times have you been married? Why did they end?
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 watch it? What is your favorite?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
5~ When you first started having sex, was it what you thought it would be?
22- What is your favorite childhood memory? What is your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
13- How about having a certain hair cut/style?
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?
19- What’s your favorite fairytale? What’s your least favorite?
48~ Do you have any siblings? Are you close to your family?
*** Questions About Me ***
(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…)
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
What is your view on sex? Meaning, When/Where/ How often/
Will you cheat again? How can, you be sure? Define what cheating is to you.
80~ Share your top three fantasies/desires. (Be detailed) 😊
19~ Who/when was your first “heartbreak”?
Do you like the “69” position? Do you prefer to be on top or bottom?
13~ Is there a difference between, making love, having sex, and fucking?
92~ Have you ever had or have an STD? How many? What was it?
3- What Superhero or Superpower would you want to be/have?
48~ Have you ever paid or been paid for sex?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
15- What's your favorite saying? What word or phrase is your least favorite?
12- What is the weirdest thing you've ever eaten?
33- Beach or Mountains? Or is there another place to like better?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Have you ever? Care to Share?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Do you have a favorite? Is it ok if your partner does?
5- Have you ever been hypnotized? Would you allow yourself to be?
1- What was your first impression of me? Has it changed?
*** Questions about Relationships/Past ***
What’s the longest time you gone without having sex, after, having it? How much time between the others?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
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?
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?
29~ What are some things that turn you off? What is your biggest turn off?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
22- Do you have any birth marks? How about scars? Care to share how you got them?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?