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