What is the most interesting question you can ask to get to know someone?
12.06.2025 09:57
34- Ever been to a concert? What was your favorite? Who would you like to see?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Any that are a turn off?
When will dating stop being so hard for Gen Z?
Would you read them together?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
83~ How do you feel about Porn?
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Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
I would allow you to do it… What would you do to me?
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* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you like it when they show and tell you what they want?
17- Have you ever done drugs? Which ones? How often?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
27- What was/ is nickname? Does it have a meaning behind it?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
40~ What’s the weirdest place you’ve ever had sex?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
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11- What's your favorite restaurant? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Can men enjoy receiving anal sex?
62~ Have you used adult toys?
29~ What are some things that turn you off? What is your biggest turn off?
*** Deal Breaker Questions ***
Has a psychic ever made a crazy prediction that turned out to be true?
8- What's your favorite flavor of ice cream? Do you a least favorite?
61~ How willing would you be to try new sexual positions?
9- If you could have three wishes, what would they be? Why?
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21- What's your favorite way to spend a weekend or time off?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
19- Do/have you smoked? What do you prefer? How often?
What are some common lies that addicts may tell themselves?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
14- What's your favorite dessert? Do you a least favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Why do some people dislike Gilmore girls?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
25~ How do you feel about PDA? (Public Display of Affection)
31- If given a chance to be immortal, would you take it? Why?
Master/Slave Boss/Maid
Have you ever forcibly sucked someone’s dick?
18~ Who/when was your first “crush”?
71~ Would you give your partner a hand or foot job? Would you receive one?
Would you do it again, and would you rather 2 females or 2 males?
What is the best sex you have ever had (in detail)?
12- What’s your favorite food? What’s your least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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Escort/Client Job Applicant/Hiring Manager
Have you ever? Care to Share?
92~ Everyone needs a “safe” word. What is yours?
How many partners have you had oral sex with? Who? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
10- List 5 of your top pet peeves.
What have you learned about yourself that you did not before this?
18- How often do you drink alcohol? What is your favorite drink?
7- What are your thoughts on religion? Is there an afterlife?
84~ How do you feel about reading/listening to adult stories?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
1- What’s your favorite animal? Do you a least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
92~ Have you ever had or have an STD? How many? What was it?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Would you allow me to clean every part of your body with my soapy hands and fingers?
9~ How many times over your lifetime do you think you have had sex so far?
3- What’s your favorite smell? Do you a least favorite?
76~ Have you had a threesome? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
50~ How many children do you have? What are their ages?
89~ Do you like taking showers together?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How many times do you think you have “made love”?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
*** Questions about Relationships/Past ***
52~ Are you willing to make “those types” of bets with your partner?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
53~ How much can you tell me about the one thing you are most passionate about?
If NO, would you ever have one? Would it be with 2 men or 2 women?
67~ Do you like it when your partner moans and/or is vocal during sex?
If you win, what will you make them do?
33- Beach or Mountains? Or is there another place to like better?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
How old are you? Male or Female?
13- How about having a certain hair cut/style?
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?
10~ How many dates are necessary before you to have sex with someone?
5~ When you first started having sex, was it what you thought it would be?
80~ Share your top three fantasies/desires. (Be detailed) 😊
7- What if a person smells a certain way? 8- How about smoking?
Over time has your thoughts on sex changed?
Nothing too Serious
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
28~ What are some things that turn on? What is your biggest turn on?
13- What’s your favorite drink? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How well do you know me? And some of your thoughts about me
11- How about if they like a certain sports team? 12-How about drinking too much?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
You know that I will be 100% truthful, so ask.
If you say it, I will stop, and we can talk about it when you are ready.
Do you like the “69” position? Do you prefer to be on top or bottom?
6- Do you have dreams? Can you remember them? What do you usually dream about?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
65~ Describe the best orgasm you’ve ever had? Care to share?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
44~ Care to share something about yourself that no one else knows about you?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
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?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
29- How superstitious are you?
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?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
47~ What would be your dream job and why?
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…
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
7-What do I do in bed that drives you wild? How about, what turns you off?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
48~ Do you have any siblings? Are you close to your family?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
*** What’s Your Favorite…? ***
22~ What is the best pickup line anyone has ever used on you? What was the worst?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Can you Deep Throat? Do you like the taste of yourself?
15~ Have you ever been “in love”? Who? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
9- What’s your favorite season and why? What’s your least favorite?
1- What was your first impression of me? Has it changed?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
33- If you could visit any time period, when would you pick? Please explain why?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Do you watch it? What is your favorite?
23- What is your dream job? What was it as a child?
1~ How old were you when you had your first kiss? Who? Care to Share?
Nurse/Patient Celebrity/Fan
Will you cheat again? How can, you be sure? Define what cheating is to you.
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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)
*** Random Questions ***
51~ What tends to bring a smile to your face?
10- What is your favorite family tradition? What’s your 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?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
The Ice Breaker Questions
Please share Did you stop?
Do you have a favorite? Is it ok if your partner does?
What have you learned about me that was new and/or surprising?
Get this wrong and this could mean the end… :-) some funny, some not…
How about if they talk dirty and/or call you names?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
Prisoner/Prison Guard Landlord/Tenant
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
52~ What are your hobbies?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
26~ What side of the bed do you sleep on?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
12- What is the weirdest thing you've ever eaten?
82~ Do you have any fantasies involving Role-Playing?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Any that are a turn off?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
37- Do you like your name? If you could change it, what would you change it too?
What would you say to prove to yourself that it was really you?
30~ What's something unexpected that turns you on?
What is your favorite position? Why?
Would you ever want to be woken up with oral and/or intercourse?
Doctor/Nurse Stripper/Client
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?
11- List at least 5 things on your bucket list. Have you done any of them already?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
38~ Share your most embarrassing sexual memory?
49~ How many times have you been married? Why did they end?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
13- What is the craziest/scariest thing you've ever done?
81~ Do you have any kinks and/or fetishes?
19- What’s your favorite fairytale? What’s your least favorite?
3- What Superhero or Superpower would you want to be/have?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
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?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
15- What bad habit do you wish you could quit? Do you have any addictions?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
What was the longest? What was the shortest?
3- Should Pluto still be considered a planet? 4- How about smoking?
13~ Is there a difference between, making love, having sex, and fucking?
Repairman/Lonely Wife Virgin/Experienced
2- What’s your favorite color? Do you a least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
* Give a rating for each one (0-100)
Would /have you ever given your partner a lap dance and Striptease?
48~ Have you ever paid or been paid for sex?
42~ What’s your biggest regret in life?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
5- Have you ever been hypnotized? Would you allow yourself to be?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
17- What’s your favorite holiday? 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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
19~ Who/when was your first “heartbreak”?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
28- What are some things that people do that irritate you?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
11~ Have you ever been caught by your parents or children or others while having sex?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
70~ Would/do you have/like anal sex?
*** Questions About Me ***
What is your favorite toy? Ever wanted to try a specific toy?
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 think this brought you closer together?
Does the thought excite you? Care to share?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
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…
60~ How important is oral sex? Do you like receiving? Do you like giving?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
34~ Do you like the lights on or off during sex?
Would you mind if your partner watched it? How about together vs alone?
8- What are your thoughts on politics?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
4- For a pet, Cat, dog or other?
(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…)
Family Relation Age Play
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
32- What's your greatest talent? Can I see it right now?
If yes, what?
Model/Photographer Police/Criminal
What do you dislike about me? I asked you to be 100% honest.
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,
21~ What was the best date you ever went on? What has been the worst?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
39~ What are your love languages?
51~ Are you willing to play adult games with your partner?
20- What’s your favorite candy? What’s your least favorite?
That one or two things that made you go hmmmm, OMG or wow!