What is the most interesting question you can ask to get to know someone?
11.06.2025 06:45
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
26~ What side of the bed do you sleep on?
27- What was/ is nickname? Does it have a meaning behind it?
44~ Care to share something about yourself that no one else knows about you?
15~ Have you ever been “in love”? Who? Care to Share?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
22- What is your favorite childhood memory? What is your least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
What type of sex do women prefer, oral, anal, or vaginal?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
48~ Do you have any siblings? Are you close to your family?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
How do women feel when they are in love?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
47~ What would be your dream job and why?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
What are some good Caribbean islands to travel to with friends or family? Why?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
1- What’s your favorite animal? 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?
Is it wrong of me to feel uncomfortable that my friend thinks my brother is hot?
14- What's your favorite dessert? Do you a least favorite?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Would you allow me to clean every part of your body with my soapy hands and fingers?
14- What is an embarrassing moment in your life? How about your most embarrassing?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Master/Slave Boss/Maid
Why was Boromir corrupted by the One Ring, but not Faramir in The Lord of the Rings?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
13- How about having a certain hair cut/style?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Can Djokovic climb the mountain? - Roland Garros
Does the thought excite you? Care to share?
How about if they talk dirty and/or call you names?
7-What do I do in bed that drives you wild? How about, what turns you off?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
How many partners have you had oral sex with? Who? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
Why were the Japanese soldiers in WW II so hesitant to surrender in battle?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
Get this wrong and this could mean the end… :-) some funny, some not…
What have you learned about me that was new and/or surprising?
61~ How willing would you be to try new sexual positions?
28~ What are some things that turn on? What is your biggest turn on?
*** Questions About Me ***
Nothing too Serious
62~ Have you used adult toys?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
17- What’s your favorite holiday? What’s your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
38~ Share your most embarrassing sexual memory?
That one or two things that made you go hmmmm, OMG or wow!
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
22- Do you have any birth marks? How about scars? Care to share how you got them?
What is your view on sex? Meaning, When/Where/ How often/
9~ How many times over your lifetime do you think you have had sex so far?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
1~ How old were you when you had your first kiss? Who? Care to Share?
13- What’s your favorite drink? What’s your least favorite?
51~ What tends to bring a smile to your face?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
2- What’s your favorite color? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
If YES, was it with 2 men or 2 women? Did you enjoy it?
5- Have you ever been hypnotized? Would you allow yourself to be?
Escort/Client Job Applicant/Hiring Manager
The Ice Breaker Questions
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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?
I would allow you to do it… What would you do to me?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
21- What's your favorite way to spend a weekend or time off?
51~ Are you willing to play adult games with your partner?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
13- What is the craziest/scariest thing you've ever done?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
53~ How much can you tell me about the one thing you are most passionate about?
11- How about if they like a certain sports team? 12-How about drinking too much?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
You know that I will be 100% truthful, so ask.
10- What is your favorite family tradition? What’s your least favorite?
How well do you know me? And some of your thoughts 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?
Can you Deep Throat? Do you like the taste of yourself?
18~ Who/when was your first “crush”?
13~ Is there a difference between, making love, having sex, and fucking?
* Give a rating for each one (0-100)
Model/Photographer Police/Criminal
Have you ever? Care to Share?
42~ What’s your biggest regret in life?
What have you learned about yourself that you did not before this?
30~ What's something unexpected that turns you on?
19~ Who/when was your first “heartbreak”?
Prisoner/Prison Guard Landlord/Tenant
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
32- What's your greatest talent? Can I see it right now?
20- What’s your favorite candy? What’s your least favorite?
83~ How do you feel about Porn?
Doctor/Nurse Stripper/Client
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
10- List 5 of your top pet peeves.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
60~ How important is oral sex? Do you like receiving? Do you like giving?
Any that are a turn off?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
33- If you could visit any time period, when would you pick? Please explain why?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
19- Do/have you smoked? What do you prefer? How often?
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…
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
3- What Superhero or Superpower would you want to be/have?
Would you read them together?
33- Beach or Mountains? Or is there another place to like better?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
12- What’s your favorite food? What’s your least favorite?
52~ Are you willing to make “those types” of bets with your partner?
Nurse/Patient Celebrity/Fan
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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…
What was the longest? What was the shortest?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
*** Random Questions ***
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?
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 is your favorite position? Why?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Please share Did you stop?
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?
65~ Describe the best orgasm you’ve ever had? Care to share?
Family Relation Age Play
What would you say to prove to yourself that it was really you?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
23- What is your dream job? What was it as a child?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
48~ Have you ever paid or been paid for sex?
11- What's your favorite restaurant? What’s your least favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
21~ What was the best date you ever went on? What has been the worst?
71~ Would you give your partner a hand or foot job? Would you receive one?
81~ Do you have any kinks and/or fetishes?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
11~ Have you ever been caught by your parents or children or others while having sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Do you watch it? What is your favorite?
4- For a pet, Cat, dog or other?
15- What bad habit do you wish you could quit? Do you have any addictions?
67~ Do you like it when your partner moans and/or is vocal during sex?
31- If given a chance to be immortal, would you take it? Why?
If NO, would you ever have one? Would it be with 2 men or 2 women?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
70~ Would/do you have/like anal sex?
7- What are your thoughts on religion? Is there an afterlife?
Would you do it again, and would you rather 2 females or 2 males?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Would /have you ever given your partner a lap dance and Striptease?
29~ What are some things that turn you off? What is your biggest turn off?
If yes, what?
7- What if a person smells a certain way? 8- How about smoking?
28- What are some things that people do that irritate you?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
8- What are your thoughts on politics?
*** Deal Breaker Questions ***
29- How superstitious are you?
40~ What’s the weirdest place you’ve ever had sex?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Over time has your thoughts on sex changed?
19- What’s your favorite fairytale? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
36~ What is your favorite time of day to have sex/make love?
Do you like the “69” position? Do you prefer to be on top or bottom?
Will you cheat again? How can, you be sure? Define what cheating is to you.
5~ When you first started having sex, was it what you thought it would be?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What is your favorite toy? Ever wanted to try a specific toy?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
18- How often do you drink alcohol? What is your favorite drink?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
Repairman/Lonely Wife Virgin/Experienced
37- Do you like your name? If you could change it, what would you change it too?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What do you dislike about me? I asked you to be 100% honest.
Would you ever want to be woken up with oral and/or intercourse?
Any that are a turn off?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
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?
Would you mind if your partner watched it? How about together vs alone?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3- Should Pluto still be considered a planet? 4- How about smoking?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
92~ Have you ever had or have an STD? How many? What was it?
34~ Do you like the lights on or off during sex?
If you win, what will you make them do?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
82~ Do you have any fantasies involving Role-Playing?
17- Have you ever done drugs? Which ones? How often?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
Teacher/Student Stranger/One Night Stand
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,
Do you think this brought you closer together?
How many times do you think you have “made love”?
6- Do you have dreams? Can you remember them? What do you usually dream about?
92~ Everyone needs a “safe” word. What is yours?
12- What is the weirdest thing you've ever eaten?
*** What’s Your Favorite…? ***
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Do you like it when they show and tell you what they want?
1- What was your first impression of me? Has it changed?
89~ Do you like taking showers together?
Do you have a favorite? Is it ok if your partner does?
76~ Have you had a threesome? Care to Share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
*** Questions about Relationships/Past ***
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
50~ How many children do you have? What are their ages?
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?
52~ What are your hobbies?
49~ How many times have you been married? Why did they end?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
If you say it, I will stop, and we can talk about it when you are ready.
80~ Share your top three fantasies/desires. (Be detailed) 😊
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
25~ How do you feel about PDA? (Public Display of Affection)
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?
(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…)
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
9- If you could have three wishes, what would they be? Why?
39~ What are your love languages?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
How old are you? Male or Female?
84~ How do you feel about reading/listening to adult stories?