What is the most interesting question you can ask to get to know someone?
Last Updated: 26.06.2025 02:13
17- What’s your favorite holiday? What’s your least favorite?
22- What is your favorite childhood memory? What is your least favorite?
89~ Do you like taking showers together?
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92~ Have you ever had or have an STD? How many? What was it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
18- What’s your favorite way to relax after a long day? What’s your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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33- Beach or Mountains? Or is there another place to like better?
Nurse/Patient Celebrity/Fan
*** Questions About Me ***
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78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
83~ How do you feel about Porn?
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15~ Have you ever been “in love”? Who? Care to Share?
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?
What is your favorite toy? Ever wanted to try a specific toy?
Infrared contact lens enables humans to see in dark - DW
What have you learned about me that was new and/or surprising?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
19~ Who/when was your first “heartbreak”?
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* Which of the following turns you on the most? Do you have any not on this list? Care to share?
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?
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19- Do/have you smoked? What do you prefer? How often?
*** What’s Your Favorite…? ***
10- List 5 of your top pet peeves.
Cannabis use in any form directly linked to significant risk of heart damage - Earth.com
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Can you Deep Throat? Do you like the taste of yourself?
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30- Do you prefer living in the countryside, in a town, or in a big city? Why?
4- For a pet, Cat, dog or other?
18- How often do you drink alcohol? What is your favorite drink?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
The Ice Breaker Questions
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
Will you cheat again? How can, you be sure? Define what cheating is to you.
27- What was/ is nickname? Does it have a meaning behind it?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
11- List at least 5 things on your bucket list. Have you done any of them already?
26~ What side of the bed do you sleep on?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
62~ Have you used adult toys?
10~ How many dates are necessary before you to have sex with someone?
48~ Do you have any siblings? Are you close to your family?
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?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
If NO, would you ever have one? Would it be with 2 men or 2 women?
84~ How do you feel about reading/listening to adult stories?
38~ Share your most embarrassing sexual memory?
52~ What are your hobbies?
39~ What are your love languages?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
11- What's your favorite restaurant? What’s your least favorite?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
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?
I would allow you to do it… What would you do to me?
29~ What are some things that turn you off? What is your biggest turn off?
How about if they talk dirty and/or call you names?
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?
13- What is the craziest/scariest thing you've ever done?
Any that are a turn off?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
How many partners have you had oral sex with? Who? Care to Share?
Would /have you ever given your partner a lap dance and Striptease?
Repairman/Lonely Wife Virgin/Experienced
36- Do you play video games? What is your favorite? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
What was the longest? What was the shortest?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
3- What’s your favorite smell? Do you a least favorite?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
14- What's your favorite dessert? Do you a least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
Please share Did you stop?
Do you like it when they show and tell you what they want?
36~ What is your favorite time of day to have sex/make love?
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?
1- What’s your favorite animal? Do you a least favorite?
71~ Would you give your partner a hand or foot job? Would you receive one?
25~ How do you feel about PDA? (Public Display of Affection)
17- Have you ever done drugs? Which ones? How often?
21~ What was the best date you ever went on? What has been the worst?
What is your favorite position? Why?
7- What if a person smells a certain way? 8- How about smoking?
Master/Slave Boss/Maid
3- What Superhero or Superpower would you want to be/have?
What would you say to prove to yourself that it was really you?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
7- What are your thoughts on religion? Is there an afterlife?
9- Is there something you’ve always wanted to ask me but you’re afraid?
7-What do I do in bed that drives you wild? How about, what turns you off?
6- Do you have dreams? Can you remember them? What do you usually dream about?
*** Questions about Relationships/Past ***
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
30~ What's something unexpected that turns you on?
13~ Is there a difference between, making love, having sex, and fucking?
What is your view on sex? Meaning, When/Where/ How often/
That one or two things that made you go hmmmm, OMG or wow!
64~ When was your very first orgasm? When was your first from having sex? Care to share?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
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,
3- Should Pluto still be considered a planet? 4- How about smoking?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
*** Random Questions ***
24~ What are your expectations in a relationship? (I know a very big question, take your time)
40~ What’s the weirdest place you’ve ever had sex?
Teacher/Student Stranger/One Night Stand
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Over time has your thoughts on sex changed?
33- If you could visit any time period, when would you pick? Please explain why?
If YES, was it with 2 men or 2 women? Did you enjoy it?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
70~ Would/do you have/like anal sex?
19- What’s your favorite fairytale? What’s your least favorite?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Would you do it again, and would you rather 2 females or 2 males?
42~ What’s your biggest regret in life?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
49~ How many times have you been married? Why did they end?
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…
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Do you watch it? What is your favorite?
9- If you could have three wishes, what would they be? Why?
What do you dislike about me? I asked you to be 100% honest.
Do you have a favorite? Is it ok if your partner does?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Get this wrong and this could mean the end… :-) some funny, some not…
29- How superstitious are you?
How well do you know me? And some of your thoughts about me
Would you allow me to clean every part of your body with my soapy hands and fingers?
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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
You know that I will be 100% truthful, so ask.
51~ What tends to bring a smile to your face?
48~ Have you ever paid or been paid for sex?
Prisoner/Prison Guard Landlord/Tenant
81~ Do you have any kinks and/or fetishes?
*** Deal Breaker Questions ***
50~ How many children do you have? What are their ages?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
31- If given a chance to be immortal, would you take it? Why?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
92~ Everyone needs a “safe” word. What is yours?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
53~ How much can you tell me about the one thing you are most passionate about?
65~ Describe the best orgasm you’ve ever had? Care to share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
How many times do you think you have “made love”?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Escort/Client Job Applicant/Hiring Manager
10- What is your favorite family tradition? What’s your least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
28~ What are some things that turn on? What is your biggest turn on?
11- How about if they like a certain sports team? 12-How about drinking too much?
12- What’s your favorite food? What’s your least favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
9- What’s your favorite season and why? What’s your least favorite?
5~ When you first started having sex, was it what you thought it would be?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
22- Do you have any birth marks? How about scars? Care to share how you got them?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
(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…)
47~ What would be your dream job and why?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
How old are you? Male or Female?
45~ How do you feel about me blindfolding you? How about blindfolding me?
12- What is the weirdest thing you've ever eaten?
Model/Photographer Police/Criminal
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
34~ Do you like the lights on or off during sex?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
67~ Do you like it when your partner moans and/or is vocal during sex?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
60~ How important is oral sex? Do you like receiving? Do you like giving?
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?
18~ Who/when was your first “crush”?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
51~ Are you willing to play adult games with your partner?
Have you ever? Care to Share?
Doctor/Nurse Stripper/Client
If yes, what?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
Do you like the “69” position? Do you prefer to be on top or bottom?
82~ Do you have any fantasies involving Role-Playing?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Family Relation Age Play
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
23- What is your dream job? What was it as a child?
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…
13- What’s your favorite drink? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
21- What's your favorite way to spend a weekend or time off?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
1- What was your first impression of me? Has it changed?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
If you win, what will you make them do?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
28- What are some things that people do that irritate you?
15- What bad habit do you wish you could quit? Do you have any addictions?
76~ Have you had a threesome? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
9~ How many times over your lifetime do you think you have had sex so far?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
* Give a rating for each one (0-100)
44~ Care to share something about yourself that no one else knows about you?
37- Do you like your name? If you could change it, what would you change it too?
11~ Have you ever been caught by your parents or children or others while having sex?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Nothing too Serious
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)
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What have you learned about yourself that you did not before this?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
14- What is an embarrassing moment in your life? How about your most embarrassing?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
20- What’s your favorite candy? What’s your least favorite?
13- How about having a certain hair cut/style?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Any that are a turn off?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
52~ Are you willing to make “those types” of bets with your partner?
Does the thought excite you? Care to share?
8- What are your thoughts on politics?
2- What’s your favorite color? Do you a least favorite?
61~ How willing would you be to try new sexual positions?
1~ How old were you when you had your first kiss? Who? Care to Share?
Do you think this brought you closer together?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
Would you read them together?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would you mind if your partner watched it? How about together vs alone?