What is the most interesting question you can ask to get to know someone?
Last Updated: 01.07.2025 16:59
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would you allow me to clean every part of your body with my soapy hands and fingers?
That one or two things that made you go hmmmm, OMG or wow!
18- What’s your favorite way to relax after a long day? What’s your least favorite?
29- How superstitious are you?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Do you have a favorite? Is it ok if your partner does?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
50~ How many children do you have? What are their ages?
52~ Are you willing to make “those types” of bets with your partner?
What's a memory from your childhood that shaped who you are today?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
30~ What's something unexpected that turns you on?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
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If YES, was it with 2 men or 2 women? Did you enjoy it?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
48~ Have you ever paid or been paid for sex?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
38~ Share your most embarrassing sexual memory?
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How about if they talk dirty and/or call you names?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What is your view on sex? Meaning, When/Where/ How often/
If you say it, I will stop, and we can talk about it when you are ready.
13~ Is there a difference between, making love, having sex, and fucking?
23- What is your dream job? What was it as a child?
What is the best case of “You just picked a fight with the wrong person” that you've witnessed?
Model/Photographer Police/Criminal
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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
How many girls or guys keep extra pantyhose in their glove box or console of their vehicle?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Can bosses get fired for being too hard on employees?
What have you learned about me that was new and/or surprising?
Family Relation Age Play
Master/Slave Boss/Maid
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43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
1- What’s your favorite animal? Do you a least favorite?
15~ Have you ever been “in love”? Who? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5- Have you ever been hypnotized? Would you allow yourself to be?
15- What's your favorite saying? What word or phrase is your least favorite?
89~ Do you like taking showers together?
17- What’s your favorite holiday? What’s your least favorite?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
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?
9- If you could have three wishes, what would they be? Why?
11- What's your favorite restaurant? What’s your least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Would you ever want to be woken up with oral and/or intercourse?
14- What's your favorite dessert? Do you a least favorite?
20- What’s your favorite candy? What’s your least favorite?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
13- What’s your favorite drink? What’s your least favorite?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
4- For a pet, Cat, dog or other?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
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?
How many partners have you had oral sex with? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
11- How about if they like a certain sports team? 12-How about drinking too much?
What is your favorite toy? Ever wanted to try a specific toy?
36~ What is your favorite time of day to have sex/make love?
Would you do it again, and would you rather 2 females or 2 males?
Nothing too Serious
8- What are your thoughts on politics?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
2- What’s your favorite color? Do you a least favorite?
28- What are some things that people do that irritate you?
You know that I will be 100% truthful, so ask.
70~ Would/do you have/like anal sex?
12- What’s your favorite food? What’s your least favorite?
52~ What are your hobbies?
I would allow you to do it… What would you do to me?
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?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
25~ How do you feel about PDA? (Public Display of Affection)
Get this wrong and this could mean the end… :-) some funny, some not…
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
13- How about having a certain hair cut/style?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
How many times do you think you have “made love”?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you watch it? What is your favorite?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
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?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
17- Have you ever done drugs? Which ones? How often?
Doctor/Nurse Stripper/Client
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?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
34~ Do you like the lights on or off during sex?
36- Do you play video games? What is your favorite? Do you a least favorite?
What would you say to prove to yourself that it was really you?
14- What is an embarrassing moment in your life? How about your most embarrassing?
84~ How do you feel about reading/listening to adult stories?
9- Is there something you’ve always wanted to ask me but you’re afraid?
40~ What’s the weirdest place you’ve ever had sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
What was the longest? What was the shortest?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
9~ How many times over your lifetime do you think you have had sex so far?
6- Do you have dreams? Can you remember them? What do you usually dream about?
61~ How willing would you be to try new sexual positions?
1- What was your first impression of me? Has it changed?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
*** Deal Breaker Questions ***
76~ Have you had a threesome? Care to Share?
What have you learned about yourself that you did not before this?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
*** What’s Your Favorite…? ***
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
*** Questions About Me ***
9- What’s your favorite season and why? What’s your least favorite?
81~ Do you have any kinks and/or fetishes?
Teacher/Student Stranger/One Night Stand
49~ If you could, would you want to be the opposite sex for a day, week, or year?
3- Should Pluto still be considered a planet? 4- How about smoking?
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)
(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…)
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
22- Do you have any birth marks? How about scars? Care to share how you got them?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
21- What's your favorite way to spend a weekend or time off?
27- What was/ is nickname? Does it have a meaning behind it?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
18- How often do you drink alcohol? What is your favorite drink?
If yes, what?
*** Random Questions ***
92~ Have you ever had or have an STD? How many? What was it?
22- What is your favorite childhood memory? What is your least favorite?
What is your favorite position? Why?
31- If given a chance to be immortal, would you take it? Why?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
How old are you? Male or Female?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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…
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Would you mind if your partner watched it? How about together vs alone?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
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?
Can you Deep Throat? Do you like the taste of yourself?
Do you like the “69” position? Do you prefer to be on top or bottom?
19- What’s your favorite fairytale? What’s your least favorite?
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,
Have you ever? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How well do you know me? And some of your thoughts about me
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
42~ What’s your biggest regret in life?
Repairman/Lonely Wife Virgin/Experienced
Any that are a turn off?
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 NO, would you ever have one? Would it be with 2 men or 2 women?
83~ How do you feel about Porn?
Nurse/Patient Celebrity/Fan
22~ What is the best pickup line anyone has ever used on you? What was the worst?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Will you cheat again? How can, you be sure? Define what cheating is to you.
41~ Are there moments in your past that you would want to change? Please share 3 of them.
80~ Share your top three fantasies/desires. (Be detailed) 😊
10~ How many dates are necessary before you to have sex with someone?
13- What is the craziest/scariest thing you've ever done?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Do you like it when they show and tell you what they want?
51~ Are you willing to play adult games with your partner?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
47~ What would be your dream job and why?
49~ How many times have you been married? Why did they end?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
51~ What tends to bring a smile to your face?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
7- What are your thoughts on religion? Is there an afterlife?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
28~ What are some things that turn on? What is your biggest turn on?
Over time has your thoughts on sex changed?
7- What if a person smells a certain way? 8- How about smoking?
Prisoner/Prison Guard Landlord/Tenant
What do you dislike about me? I asked you to be 100% honest.
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
* Give a rating for each one (0-100)
18~ Who/when was your first “crush”?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
Escort/Client Job Applicant/Hiring Manager
1~ How old were you when you had your first kiss? Who? Care to Share?
37- Do you like your name? If you could change it, what would you change it too?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Would /have you ever given your partner a lap dance and Striptease?
15- What bad habit do you wish you could quit? Do you have any addictions?
48~ Do you have any siblings? Are you close to your family?
10- What is your favorite family tradition? What’s your least favorite?
11~ Have you ever been caught by your parents or children or others while having sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
33- If you could visit any time period, when would you pick? Please explain why?
39~ What are your love languages?
3- What Superhero or Superpower would you want to be/have?
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?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
44~ Care to share something about yourself that no one else knows about you?
Do you think this brought you closer together?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
*** Questions about Relationships/Past ***
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
The Ice Breaker Questions
29~ What are some things that turn you off? What is your biggest turn off?
53~ How much can you tell me about the one thing you are most passionate about?
If you win, what will you make them do?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
65~ Describe the best orgasm you’ve ever had? Care to share?
12- What is the weirdest thing you've ever eaten?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
32- What's your greatest talent? Can I see it right now?
19~ Who/when was your first “heartbreak”?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
11- List at least 5 things on your bucket list. Have you done any of them already?
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…
3- What’s your favorite smell? Do you a least favorite?
Does the thought excite you? Care to share?
33- Beach or Mountains? Or is there another place to like better?
26~ What side of the bed do you sleep on?
5~ When you first started having sex, was it what you thought it would be?
8- What's your favorite flavor of ice cream? Do you a least favorite?
19- Do/have you smoked? What do you prefer? How often?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
62~ Have you used adult toys?
Would you read them together?
67~ Do you like it when your partner moans and/or is vocal during sex?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
45~ How do you feel about me blindfolding you? How about blindfolding me?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (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.
Any that are a turn off?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
10- List 5 of your top pet peeves.
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
7-What do I do in bed that drives you wild? How about, what turns you off?
Please share Did you stop?