What is the most interesting question you can ask to get to know someone?
08.06.2025 14:13
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
13- What’s your favorite drink? What’s your least favorite?
8- What are your thoughts on politics?
Why do I sweat between my legs all the time, top off my legs, all way down?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
48~ Do you have any siblings? Are you close to your family?
19- What’s your favorite fairytale? What’s your least favorite?
Can a Trump supporter explain what was wrong with what Bishop Budde said to Donald Trump?
Model/Photographer Police/Criminal
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
What is the most offensive thing someone has ever asked you?
31- If given a chance to be immortal, would you take it? Why?
Please share Did you stop?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
What movies and TV shows portray realistic beauty standards?
Over time has your thoughts on sex changed?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
89~ Do you like taking showers together?
Why has Biden pulled ahead in battleground states and is now projected to win the 2024 presidency?
If you say it, I will stop, and we can talk about it when you are ready.
26~ What side of the bed do you sleep on?
Do you like it when they show and tell you what they want?
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?
Would you read them together?
Inside ‘Inside the NBA’ Transition to ESPN - Front Office Sports
The Ice Breaker Questions
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…
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?
Trump is forcing this dirty, costly coal plant to stay open - The Washington Post
38~ Share your most embarrassing sexual memory?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
*** Questions about Relationships/Past ***
How can I easily get rid of my writers block?
25~ How do you feel about PDA? (Public Display of Affection)
12- What is the weirdest thing you've ever eaten?
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?
How do I get a white man for a serious relationship?
2- What’s your favorite color? Do you a least favorite?
How many partners have you had oral sex with? Who? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
5- Have you ever been hypnotized? Would you allow yourself to be?
81~ Do you have any kinks and/or fetishes?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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?
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
33- Beach or Mountains? Or is there another place to like better?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
What have you learned about me that was new and/or surprising?
What is your favorite position? Why?
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,
3- Should Pluto still be considered a planet? 4- How about smoking?
Do you like the “69” position? Do you prefer to be on top or bottom?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
80~ Share your top three fantasies/desires. (Be detailed) 😊
39~ What are your love languages?
Escort/Client Job Applicant/Hiring Manager
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
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?
14- What's your favorite dessert? 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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
34- Ever been to a concert? What was your favorite? Who would you like to see?
13- How about having a certain hair cut/style?
Get this wrong and this could mean the end… :-) some funny, some not…
11- What's your favorite restaurant? What’s your least favorite?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
17- What’s your favorite holiday? What’s your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
That one or two things that made you go hmmmm, OMG or wow!
60~ How important is oral sex? Do you like receiving? Do you like giving?
Master/Slave Boss/Maid
*** Questions About Me ***
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…
29- How superstitious are you?
How old are you? Male or Female?
If NO, would you ever have one? Would it be with 2 men or 2 women?
45~ How do you feel about me blindfolding you? How about blindfolding me?
50~ How many children do you have? What are their ages?
13- What is the craziest/scariest thing you've ever done?
52~ What are your hobbies?
Would you mind if your partner watched it? How about together vs alone?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
15- What's your favorite saying? What word or phrase is your least favorite?
Any that are a turn off?
Do you have a favorite? Is it ok if your partner does?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
51~ What tends to bring a smile to your face?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
You know that I will be 100% truthful, so ask.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
22- Do you have any birth marks? How about scars? Care to share how you got them?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Teacher/Student Stranger/One Night Stand
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
61~ How willing would you be to try new sexual positions?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
15- What bad habit do you wish you could quit? Do you have any addictions?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
27- What was/ is nickname? Does it have a meaning behind it?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
8- What's your favorite flavor of ice cream? Do you a least favorite?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What is your view on sex? Meaning, When/Where/ How often/
Would you ever want to be woken up with oral and/or intercourse?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
21~ What was the best date you ever went on? What has been the worst?
Can you Deep Throat? Do you like the taste of yourself?
33- If you could visit any time period, when would you pick? Please explain why?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
19~ Who/when was your first “heartbreak”?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
*** Random Questions ***
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?
67~ Do you like it when your partner moans and/or is vocal during sex?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What was the longest? What was the shortest?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
What have you learned about yourself that you did not before this?
22- What is your favorite childhood memory? What is your least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
51~ Are you willing to play adult games with your partner?
11- How about if they like a certain sports team? 12-How about drinking too much?
32- What's your greatest talent? Can I see it right now?
3- What’s your favorite smell? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Do you think this brought you closer together?
Nurse/Patient Celebrity/Fan
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)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
How about if they talk dirty and/or call you names?
Would /have you ever given your partner a lap dance and Striptease?
13~ Is there a difference between, making love, having sex, and fucking?
Doctor/Nurse Stripper/Client
9~ How many times over your lifetime do you think you have had sex so far?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
18- How often do you drink alcohol? What is your favorite drink?
5~ When you first started having sex, was it what you thought it would be?
18~ Who/when was your first “crush”?
20- What’s your favorite candy? What’s your least favorite?
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?
23- What is your dream job? What was it as a child?
19- Do/have you smoked? What do you prefer? How often?
Nothing too Serious
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
37- Do you like your name? If you could change it, what would you change it too?
3- What Superhero or Superpower would you want to be/have?
92~ Everyone needs a “safe” word. What is yours?
21- What's your favorite way to spend a weekend or time off?
49~ How many times have you been married? Why did they end?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
82~ Do you have any fantasies involving Role-Playing?
Family Relation Age Play
1- What’s your favorite animal? Do you a least favorite?
*** Deal Breaker Questions ***
9- Is there something you’ve always wanted to ask me but you’re afraid?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
4- For a pet, Cat, dog or other?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
1- What was your first impression of me? Has it changed?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
11~ Have you ever been caught by your parents or children or others while having sex?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
7- What are your thoughts on religion? Is there an afterlife?
11- List at least 5 things on your bucket list. Have you done any of them already?
Prisoner/Prison Guard Landlord/Tenant
* Give a rating for each one (0-100)
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
If yes, what?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
40~ What’s the weirdest place you’ve ever had sex?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
(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…)
22~ What is the best pickup line anyone has ever used on you? What was the worst?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
42~ What’s your biggest regret in life?
*** What’s Your Favorite…? ***
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
28- What are some things that people do that irritate you?
12- What’s your favorite food? What’s your least favorite?
92~ Have you ever had or have an STD? How many? What was it?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
6- Do you have dreams? Can you remember them? What do you usually dream about?
10- What is your favorite family tradition? What’s your least favorite?
Have you ever? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
47~ What would be your dream job and why?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
53~ How much can you tell me about the one thing you are most passionate about?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
7- What if a person smells a certain way? 8- How about smoking?
76~ Have you had a threesome? Care to Share?
What would you say to prove to yourself that it was really you?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
What is your favorite toy? Ever wanted to try a specific toy?
If you win, what will you make them do?
Repairman/Lonely Wife Virgin/Experienced
I would allow you to do it… What would you do to me?
65~ Describe the best orgasm you’ve ever had? Care to share?
17~ What is the average length of your relationship(s)? What was the longest? 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?
34~ Do you like the lights on or off during sex?
62~ Have you used adult toys?
71~ Would you give your partner a hand or foot job? Would you receive one?
Any that are a turn off?
Would you do it again, and would you rather 2 females or 2 males?
29~ What are some things that turn you off? What is your biggest turn off?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
How many times do you think you have “made love”?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
30~ What's something unexpected that turns you on?
Do you watch it? What is your favorite?
83~ How do you feel about Porn?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
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?
70~ Would/do you have/like anal sex?
9- If you could have three wishes, what would they be? Why?
1~ How old were you when you had your first kiss? Who? Care to Share?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
10- List 5 of your top pet peeves.
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?
84~ How do you feel about reading/listening to adult stories?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
What do you dislike about me? I asked you to be 100% honest.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Does the thought excite you? Care to share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
10~ How many dates are necessary before you to have sex with someone?
48~ Have you ever paid or been paid for sex?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
36~ What is your favorite time of day to have sex/make love?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How well do you know me? And some of your thoughts about me