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