What is the most interesting question you can ask to get to know someone?
Last Updated: 22.06.2025 04:11

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