What is the most interesting question you can ask to get to know someone?
10.06.2025 07:24
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
That one or two things that made you go hmmmm, OMG or wow!
What is a good way to conduct an interview?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
If NO, would you ever have one? Would it be with 2 men or 2 women?
How well do you know me? And some of your thoughts about me
Playdate’s second season is off to a great (and very weird) start - The Verge
Repairman/Lonely Wife Virgin/Experienced
48~ Have you ever paid or been paid for sex?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
M’s Kirby struck in face by 103 mph line drive - Seattle Sports
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
What have you learned about yourself that you did not before this?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
*** Deal Breaker Questions ***
What happens psychologically to a man the first time he gets penetrated anally?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
37- Do you like your name? If you could change it, what would you change it too?
8- What are your thoughts on politics?
What is one thing you've learned from life?
*** Questions About Me ***
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?
89~ Do you like taking showers together?
Is it true that LGB should drop T?
17- What’s your favorite holiday? What’s your least favorite?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
2- What’s your favorite color? Do you a least favorite?
Fermenting legume pulses increases antioxidant and antidiabetic properties, study finds - Phys.org
How about if they talk dirty and/or call you names?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Knicks get Jay Wright clarity in their head coach search - New York Post
What would you say to prove to yourself that it was really you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Galerie David Guiraud : Deep Space & Celestial Objects - The Eye of Photography
7- What are your thoughts on religion? Is there an afterlife?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
36~ What is your favorite time of day to have sex/make love?
The Ice Breaker Questions
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
47~ What would be your dream job and why?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
15~ Have you ever been “in love”? Who? Care to Share?
Any that are a turn off?
Get this wrong and this could mean the end… :-) some funny, some not…
1- What’s your favorite animal? Do you a least favorite?
52~ Are you willing to make “those types” of bets with your partner?
What is your favorite toy? Ever wanted to try a specific toy?
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?
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?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
You know that I will be 100% truthful, so ask.
81~ Do you have any kinks and/or fetishes?
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?
62~ Have you used adult toys?
17- Have you ever done drugs? Which ones? How often?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Escort/Client Job Applicant/Hiring Manager
28- What are some things that people do that irritate you?
Have you ever? Care to Share?
38~ Share your most embarrassing sexual memory?
18~ Who/when was your first “crush”?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
If yes, what?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Does the thought excite you? Care to share?
44~ Care to share something about yourself that no one else knows about you?
Teacher/Student Stranger/One Night Stand
What is your view on sex? Meaning, When/Where/ How often/
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
How many times do you think you have “made love”?
9- What’s your favorite season and why? What’s your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Do you think this brought you closer together?
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…
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
51~ Are you willing to play adult games with your partner?
Nurse/Patient Celebrity/Fan
4- For a pet, Cat, dog or other?
3- Should Pluto still be considered a planet? 4- How about smoking?
If you say it, I will stop, and we can talk about it when you are ready.
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
39~ What are your love languages?
12- What is the weirdest thing you've ever eaten?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Prisoner/Prison Guard Landlord/Tenant
Master/Slave Boss/Maid
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Doctor/Nurse Stripper/Client
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
50~ How many children do you have? What are their ages?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
92~ Everyone needs a “safe” word. What is yours?
25~ How do you feel about PDA? (Public Display of Affection)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
11- How about if they like a certain sports team? 12-How about drinking too much?
33- Beach or Mountains? Or is there another place to like better?
Would you mind if your partner watched it? How about together vs alone?
5- Have you ever been hypnotized? Would you allow yourself to be?
10- List 5 of your top pet peeves.
11- What's your favorite restaurant? 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?
10- What is your favorite family tradition? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
*** What’s Your Favorite…? ***
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
14- What is an embarrassing moment in your life? How about your most embarrassing?
10~ How many dates are necessary before you to have sex with someone?
61~ How willing would you be to try new sexual positions?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
12- What’s your favorite food? What’s your least favorite?
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)
14- What's your favorite dessert? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
9- If you could have three wishes, what would they be? Why?
Family Relation Age Play
22- What is your favorite childhood memory? What is your least favorite?
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…
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
28~ What are some things that turn on? What is your biggest turn on?
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.
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
21- What's your favorite way to spend a weekend or time off?
26~ What side of the bed do you sleep on?
Would you read them together?
Over time has your thoughts on sex changed?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
80~ Share your top three fantasies/desires. (Be detailed) 😊
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
42~ What’s your biggest regret in life?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
* Give a rating for each one (0-100)
27- What was/ is nickname? Does it have a meaning behind it?
29~ What are some things that turn you off? What is your biggest turn off?
What is your favorite position? Why?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
Would you do it again, and would you rather 2 females or 2 males?
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?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Any that are a turn off?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
5~ When you first started having sex, was it what you thought it would be?
Would you ever want to be woken up with oral and/or intercourse?
84~ How do you feel about reading/listening to adult stories?
How old are you? Male or Female?
19- What’s your favorite fairytale? What’s your least favorite?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
13~ Is there a difference between, making love, having sex, and fucking?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
34- Ever been to a concert? What was your favorite? Who would you like to see?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
67~ Do you like it when your partner moans and/or is vocal during sex?
36- Do you play video games? What is your favorite? Do you a least favorite?
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?
82~ Do you have any fantasies involving Role-Playing?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
48~ Do you have any siblings? Are you close to your family?
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?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
32- What's your greatest talent? Can I see it right now?
Model/Photographer Police/Criminal
34~ Do you like the lights on or off during sex?
19- Do/have you smoked? What do you prefer? How often?
13- How about having a certain hair cut/style?
49~ How many times have you been married? Why did they end?
Please share Did you stop?
*** Random Questions ***
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
7-What do I do in bed that drives you wild? How about, what turns you off?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Nothing too Serious
45~ How do you feel about me blindfolding you? How about blindfolding me?
23- What is your dream job? What was it as a child?
22- Do you have any birth marks? How about scars? Care to share how you got them?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
19~ Who/when was your first “heartbreak”?
(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…)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
I would allow you to do it… What would you do to me?
30~ What's something unexpected that turns you on?
20- What’s your favorite candy? What’s your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
Do you like it when they show and tell you what they want?
11- List at least 5 things on your bucket list. Have you done any of them already?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
33- If you could visit any time period, when would you pick? Please explain why?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
13- What’s your favorite drink? What’s your least favorite?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
7- What if a person smells a certain way? 8- How about smoking?
What have you learned about me that was new and/or surprising?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
3- What Superhero or Superpower would you want to be/have?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
29- How superstitious are you?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
70~ Would/do you have/like anal sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
13- What is the craziest/scariest thing you've ever done?
31- If given a chance to be immortal, would you take it? Why?
How many partners have you had oral sex with? Who? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
9~ How many times over your lifetime do you think you have had sex so far?
Do you like the “69” position? Do you prefer to be on top or bottom?
8- What's your favorite flavor of ice cream? Do you a least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
What was the longest? What was the shortest?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
52~ What are your hobbies?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you watch it? What is your favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Can you Deep Throat? Do you like the taste of yourself?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
76~ Have you had a threesome? Care to Share?
83~ How do you feel about Porn?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
3- What’s your favorite smell? Do you a least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
92~ Have you ever had or have an STD? How many? What was it?
*** Questions about Relationships/Past ***
1~ How old were you when you had your first kiss? Who? Care to Share?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
If you win, what will you make them do?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
21~ What was the best date you ever went on? What has been the worst?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
1- What was your first impression of me? Has it changed?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
71~ Would you give your partner a hand or foot job? Would you receive one?
51~ What tends to bring a smile to your face?
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,
18- How often do you drink alcohol? What is your favorite drink?
Do you have a favorite? Is it ok if your partner does?