What is the most interesting question you can ask to get to know someone?
08.06.2025 03:26
If yes, what?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
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?
Teacher/Student Stranger/One Night Stand
12- What is the weirdest thing you've ever eaten?
13- How about having a certain hair cut/style?
92~ Have you ever had or have an STD? How many? What was it?
Please share Did you stop?
Any that are a turn off?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
49~ If you could, would you want to be the opposite sex for a day, week, or year?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
As a woman, what would be you response to a male friend’s offer of a full body massage?
20- What’s your favorite candy? What’s your least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Do you think this brought you closer together?
11~ Have you ever been caught by your parents or children or others while having sex?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
How do you know if your husband loves you truly and deeply?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
If YES, was it with 2 men or 2 women? Did you enjoy it?
10~ How many dates are necessary before you to have sex with someone?
Mets and Dodgers are more than living up to heavyweight billing - New York Post
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,
5~ When you first started having sex, was it what you thought it would be?
71~ Would you give your partner a hand or foot job? Would you receive one?
FDA rushed out agency-wide AI tool—it’s not going well - Ars Technica
45~ How do you feel about me blindfolding you? How about blindfolding me?
14- What is an embarrassing moment in your life? How about your most embarrassing?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Physicists observe a new form of magnetism for the first time - Phys.org
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
13~ Is there a difference between, making love, having sex, and fucking?
38~ Share your most embarrassing sexual memory?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
You know that I will be 100% truthful, so ask.
5- Have you ever been hypnotized? Would you allow yourself to be?
1- What’s your favorite animal? 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?
19- Do/have you smoked? What do you prefer? How often?
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?
*** Random Questions ***
17- What’s your favorite holiday? What’s your least favorite?
What would you say to prove to yourself that it was really you?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
7- What if a person smells a certain way? 8- How about smoking?
11- What's your favorite restaurant? What’s your least favorite?
Would you ever want to be woken up with oral and/or intercourse?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
9- Is there something you’ve always wanted to ask me but you’re afraid?
22- Do you have any birth marks? How about scars? Care to share how you got them?
15- What bad habit do you wish you could quit? Do you have any addictions?
3- Should Pluto still be considered a planet? 4- How about smoking?
19- What’s your favorite fairytale? What’s your least favorite?
*** Questions about Relationships/Past ***
13- What’s your favorite drink? What’s your least favorite?
36~ What is your favorite time of day to have sex/make love?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
32- What's your greatest talent? Can I see it right now?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
84~ How do you feel about reading/listening to adult stories?
9- What’s your favorite season and why? What’s your least favorite?
61~ How willing would you be to try new sexual positions?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
If NO, would you ever have one? Would it be with 2 men or 2 women?
52~ Are you willing to make “those types” of bets with your partner?
Nurse/Patient Celebrity/Fan
Would you do it again, and would you rather 2 females or 2 males?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
10- What is your favorite family tradition? What’s your least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
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)
What have you learned about yourself that you did not before this?
51~ What tends to bring a smile to your face?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
83~ How do you feel about Porn?
*** What’s Your Favorite…? ***
How many partners have you had oral sex with? Who? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
28~ What are some things that turn on? What is your biggest turn on?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Do you watch it? What is your favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
80~ Share your top three fantasies/desires. (Be detailed) 😊
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Any that are a turn off?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
39~ What are your love languages?
30~ What's something unexpected that turns you on?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Get this wrong and this could mean the end… :-) some funny, some not…
Can you Deep Throat? Do you like the taste of yourself?
(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…)
Have you ever? Care to Share?
76~ Have you had a threesome? Care to Share?
47~ What would be your dream job and why?
22- What is your favorite childhood memory? What is your least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
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…
9- If you could have three wishes, what would they be? Why?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
44~ Care to share something about yourself that no one else knows about you?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
1- What was your first impression of me? Has it changed?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
13- What is the craziest/scariest thing you've ever done?
28- What are some things that people do that irritate you?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
* Give a rating for each one (0-100)
How many times do you think you have “made love”?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
Prisoner/Prison Guard Landlord/Tenant
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
60~ How important is oral sex? Do you like receiving? Do you like giving?
7- What are your thoughts on religion? Is there an afterlife?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
Does the thought excite you? Care to share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
42~ What’s your biggest regret in life?
12- What’s your favorite food? What’s your least favorite?
62~ Have you used adult toys?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
What do you dislike about me? I asked you to be 100% honest.
Nothing too Serious
82~ Do you have any fantasies involving Role-Playing?
52~ What are your hobbies?
33- Beach or Mountains? Or is there another place to like better?
26~ What side of the bed do you sleep on?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
That one or two things that made you go hmmmm, OMG or wow!
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
How about if they talk dirty and/or call you names?
34~ Do you like the lights on or off during sex?
*** Deal Breaker Questions ***
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
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?
14- What's your favorite dessert? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
89~ Do you like taking showers together?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Doctor/Nurse Stripper/Client
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
How well do you know me? And some of your thoughts about me
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If you say it, I will stop, and we can talk about it when you are ready.
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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…
What is your favorite toy? Ever wanted to try a specific toy?
Would /have you ever given your partner a lap dance and Striptease?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
31- If given a chance to be immortal, would you take it? Why?
15- What's your favorite saying? What word or phrase is your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
23- What is your dream job? What was it as a child?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
18~ Who/when was your first “crush”?
What was the longest? What was the shortest?
What have you learned about me that was new and/or surprising?
53~ How much can you tell me about the one thing you are most passionate about?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
10- List 5 of your top pet peeves.
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
2- What’s your favorite color? Do you a least favorite?
Model/Photographer Police/Criminal
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
How old are you? Male or Female?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
37- Do you like your name? If you could change it, what would you change it too?
49~ How many times have you been married? Why did they end?
3- What Superhero or Superpower would you want to be/have?
81~ Do you have any kinks and/or fetishes?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
8- What's your favorite flavor of ice cream? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Escort/Client Job Applicant/Hiring Manager
What is your favorite position? Why?
Do you have a favorite? Is it ok if your partner does?
36- Do you play video games? What is your favorite? Do you a least favorite?
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 there a smell that most people do not like that you do? Is there a smell that triggers a memory?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
48~ Have you ever paid or been paid for sex?
33- If you could visit any time period, when would you pick? Please explain why?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
Family Relation Age Play
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
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?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
The Ice Breaker Questions
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
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?
48~ Do you have any siblings? Are you close to your family?
21~ What was the best date you ever went on? What has been the worst?
*** Questions About Me ***
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
50~ How many children do you have? What are their ages?
21- What's your favorite way to spend a weekend or time off?
What is your view on sex? Meaning, When/Where/ How often/
17- Have you ever done drugs? Which ones? How often?
18- How often do you drink alcohol? What is your favorite drink?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
51~ Are you willing to play adult games with your partner?
34- Ever been to a concert? What was your favorite? Who would you like to see?
29- How superstitious are you?
3- What’s your favorite smell? Do you a least favorite?
Would you read them together?
70~ Would/do you have/like anal sex?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Master/Slave Boss/Maid
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Do you like it when they show and tell you what they want?
65~ Describe the best orgasm you’ve ever had? Care to share?
Will you cheat again? How can, you be sure? Define what cheating is to you.
29~ What are some things that turn you off? What is your biggest turn off?
8- What are your thoughts on politics?
9~ How many times over your lifetime do you think you have had sex so far?
Over time has your thoughts on sex changed?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
4- For a pet, Cat, dog or other?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
19~ Who/when was your first “heartbreak”?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
If you win, what will you make them do?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?