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