What is the most interesting question you can ask to get to know someone?
14.06.2025 00:18
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
What was the longest? What was the shortest?
Would you read them together?
Why do unattractive men assume that a pretty woman like me want them?
Nothing too Serious
1~ How old were you when you had your first kiss? Who? Care to Share?
How many times do you think you have “made love”?
Would you join a gym or workout at home and why?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
21- What's your favorite way to spend a weekend or time off?
84~ How do you feel about reading/listening to adult stories?
What does the Bible say about the Antichrist? How will we know when he arrives on the scene?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Repairman/Lonely Wife Virgin/Experienced
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
All of the new features coming to Apple’s iOS apps - TechCrunch
10~ How many dates are necessary before you to have sex with someone?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If yes, what?
How do I come out as queer to my best friend in a funny and stupid way?
38~ Share your most embarrassing sexual memory?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
27- What was/ is nickname? Does it have a meaning behind it?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
51~ What tends to bring a smile to your face?
Why am I not getting any atheists to debate with? Are they scared?
37- Do you like your name? If you could change it, what would you change it too?
Nurse/Patient Celebrity/Fan
44~ Care to share something about yourself that no one else knows about you?
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,
19- What’s your favorite fairytale? What’s your least favorite?
30~ What's something unexpected that turns you on?
What is your worst experience in life?
8- What's your favorite flavor of ice cream? Do you a least favorite?
49~ How many times have you been married? Why did they end?
Will you cheat again? How can, you be sure? Define what cheating is to you.
Is it wrong of me to feel uncomfortable that my friend thinks my brother is hot?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
The Ice Breaker Questions
1- What’s your favorite animal? Do you a least favorite?
If gays can get married, why can't I marry my dog or a cheeseburger?
5- Have you ever been hypnotized? Would you allow yourself to be?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
When do you feel most peaceful ever?
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?
22- What is your favorite childhood memory? What is your least favorite?
15- What bad habit do you wish you could quit? Do you have any addictions?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
9- What’s your favorite season and why? What’s your least favorite?
Any that are a turn off?
2- What’s your favorite color? Do you a least favorite?
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?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
12- What’s your favorite food? What’s your least favorite?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
How many partners have you had oral sex with? Who? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Over time has your thoughts on sex changed?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you like the “69” position? Do you prefer to be on top or bottom?
How well do you know me? And some of your thoughts about me
*** Deal Breaker Questions ***
33- If you could visit any time period, when would you pick? Please explain why?
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?
What have you learned about yourself that you did not before this?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
92~ Everyone needs a “safe” word. What is yours?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
19~ Who/when was your first “heartbreak”?
34~ Do you like the lights on or off during sex?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
11~ Have you ever been caught by your parents or children or others while having sex?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What do you dislike about me? I asked you to be 100% honest.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Do you shave/trim your pubic hair? For you guys do you shave your balls?
11- How about if they like a certain sports team? 12-How about drinking too much?
81~ Do you have any kinks and/or fetishes?
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?
51~ Are you willing to play adult games with your partner?
70~ Would/do you have/like anal sex?
Can you Deep Throat? Do you like the taste of yourself?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
71~ Would you give your partner a hand or foot job? Would you receive one?
8- What are your thoughts on politics?
That one or two things that made you go hmmmm, OMG or wow!
29~ What are some things that turn you off? What is your biggest turn off?
5~ When you first started having sex, was it what you thought it would be?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
10- What is your favorite family tradition? 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.
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
26~ What side of the bed do you sleep on?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
7- What are your thoughts on religion? Is there an afterlife?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
I would allow you to do it… What would you do to me?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
62~ Have you used adult toys?
If NO, would you ever have one? Would it be with 2 men or 2 women?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
12- What is the weirdest thing you've ever eaten?
If YES, was it with 2 men or 2 women? Did you enjoy it?
(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…)
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Would you mind if your partner watched it? How about together vs alone?
54~ Would you ever go skinny dipping with your partner? Have you ever been? 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?
9- Is there something you’ve always wanted to ask me but you’re afraid?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
92~ Have you ever had or have an STD? How many? What was it?
48~ Do you have any siblings? Are you close to your family?
47~ What would be your dream job and why?
19- Do/have you smoked? What do you prefer? How often?
Please share Did you stop?
36- Do you play video games? What is your favorite? Do you a least favorite?
36~ What is your favorite time of day to have sex/make love?
Escort/Client Job Applicant/Hiring Manager
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
You know that I will be 100% truthful, so ask.
13- What is the craziest/scariest thing you've ever done?
17- What’s your favorite holiday? What’s your least favorite?
89~ Do you like taking showers together?
If you win, what will you make them do?
40~ What’s the weirdest place you’ve ever had sex?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
53~ How much can you tell me about the one thing you are most passionate about?
3- What’s your favorite smell? Do you a least favorite?
28- What are some things that people do that irritate you?
Prisoner/Prison Guard Landlord/Tenant
What is your favorite position? Why?
22- Do you have any birth marks? How about scars? Care to share how you got them?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
39~ What are your love languages?
Family Relation Age Play
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Do you watch it? What is your favorite?
50~ How many children do you have? What are their ages?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Would you do it again, and would you rather 2 females or 2 males?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
42~ What’s your biggest regret in life?
52~ What are your hobbies?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
*** Random Questions ***
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
18~ Who/when was your first “crush”?
34- Ever been to a concert? What was your favorite? Who would you like to see?
9~ How many times over your lifetime do you think you have had sex so far?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
82~ Do you have any fantasies involving Role-Playing?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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…
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
18- How often do you drink alcohol? What is your favorite drink?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Would you allow me to clean every part of your body with my soapy hands and fingers?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
23- What is your dream job? What was it as a child?
What is your view on sex? Meaning, When/Where/ How often/
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
13- What’s your favorite drink? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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....)
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?
Would you ever want to be woken up with oral and/or intercourse?
Would /have you ever given your partner a lap dance and Striptease?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
14- What's your favorite dessert? Do you a least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What have you learned about me that was new and/or surprising?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Do you think this brought you closer together?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
15- What's your favorite saying? What word or phrase is your least favorite?
10- List 5 of your top pet peeves.
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
11- What's your favorite restaurant? What’s your least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
33- Beach or Mountains? Or is there another place to like better?
76~ Have you had a threesome? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
7- What if a person smells a certain way? 8- How about smoking?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Get this wrong and this could mean the end… :-) some funny, some not…
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
*** Questions About Me ***
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
28~ What are some things that turn on? What is your biggest turn on?
67~ Do you like it when your partner moans and/or is vocal during sex?
Any that are a turn off?
45~ How do you feel about me blindfolding you? How about blindfolding me?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
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)
If you say it, I will stop, and we can talk about it when you are ready.
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
13- How about having a certain hair cut/style?
7-What do I do in bed that drives you wild? How about, what turns you off?
Doctor/Nurse Stripper/Client
Do you have a favorite? Is it ok if your partner does?
20- What’s your favorite candy? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
How about if they talk dirty and/or call you names?
Does the thought excite you? Care to share?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
1- What was your first impression of me? Has it changed?
31- If given a chance to be immortal, would you take it? Why?
* Give a rating for each one (0-100)
32- What's your greatest talent? Can I see it right now?
3- What Superhero or Superpower would you want to be/have?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Master/Slave Boss/Maid
9- If you could have three wishes, what would they be? Why?
61~ How willing would you be to try new sexual positions?
14- What is an embarrassing moment in your life? How about your most embarrassing?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Teacher/Student Stranger/One Night Stand
83~ How do you feel about Porn?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
*** What’s Your Favorite…? ***
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Do you like it when they show and tell you what they want?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How old are you? Male or Female?
17- Have you ever done drugs? Which ones? How often?
What would you say to prove to yourself that it was really you?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
29- How superstitious are you?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
25~ How do you feel about PDA? (Public Display of Affection)
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
4- For a pet, Cat, dog or other?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
21~ What was the best date you ever went on? What has been the worst?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
15~ Have you ever been “in love”? Who? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Model/Photographer Police/Criminal
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3- Should Pluto still be considered a planet? 4- How about smoking?
Have you ever? Care to Share?
*** Questions about Relationships/Past ***
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…