What is the most interesting question you can ask to get to know someone?
13.06.2025 12:13
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
*** What’s Your Favorite…? ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What have you learned about yourself that you did not before this?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
What have you learned about me that was new and/or surprising?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
What is a good comeback for when someone calls you flat?
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?
What is your favorite toy? Ever wanted to try a specific toy?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
40~ What’s the weirdest place you’ve ever had sex?
2- What’s your favorite color? Do you a least favorite?
What is one thing nice you did for someone today or something they did for you?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
70~ Would/do you have/like anal sex?
10- What is your favorite family tradition? What’s your least favorite?
What was the worst spanking you ever got? Why did you get it, and how was it given to you?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
13- What’s your favorite drink? What’s your least favorite?
What are the psychological reasons behind an extreme obsession with another human being?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What do porn stars do when they get old?
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,
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
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 you have multiple orgasms? Are you able to have different kinds of orgasms?
29~ What are some things that turn you off? What is your biggest turn off?
Why can’t the British eat or drink anything unless they place a table cloth on the table first?
20- What’s your favorite candy? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
19~ Who/when was your first “heartbreak”?
Nvidia CEO sends blunt 7-word message on quantum computing - TheStreet
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
84~ How do you feel about reading/listening to adult stories?
What is the most craziest dream you ever had?
67~ Do you like it when your partner moans and/or is vocal during sex?
11- What's your favorite restaurant? What’s your least favorite?
48~ Have you ever paid or been paid for sex?
What is the reason for writing X^2 as XX instead of X*X?
You know that I will be 100% truthful, so ask.
What do you dislike about me? I asked you to be 100% honest.
7- What if a person smells a certain way? 8- How about smoking?
Do other British people agree that the UK should reconquer Ireland?
Nurse/Patient Celebrity/Fan
*** Questions About Me ***
10- List 5 of your top pet peeves.
Do you have a favorite? Is it ok if your partner does?
38~ Share your most embarrassing sexual memory?
*** Deal Breaker Questions ***
If YES, was it with 2 men or 2 women? Did you enjoy it?
21~ What was the best date you ever went on? What has been the worst?
Nothing too Serious
Any that are a turn off?
27- What was/ is nickname? Does it have a meaning behind it?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
9~ How many times over your lifetime do you think you have had sex so far?
15~ Have you ever been “in love”? 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?
11- List at least 5 things on your bucket list. Have you done any of them already?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
How many times do you think you have “made love”?
Would you read them together?
How about if they talk dirty and/or call you names?
If yes, what?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would you mind if your partner watched it? How about together vs alone?
What is your view on sex? Meaning, When/Where/ How often/
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
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?
8- What are your thoughts on politics?
82~ Do you have any fantasies involving Role-Playing?
11~ Have you ever been caught by your parents or children or others while having sex?
How well do you know me? And some of your thoughts about me
1~ How old were you when you had your first kiss? Who? Care to Share?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
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!
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
*** Questions about Relationships/Past ***
51~ What tends to bring a smile to your face?
What is your favorite position? Why?
Over time has your thoughts on sex changed?
* Give a rating for each one (0-100)
17- Have you ever done drugs? Which ones? How often?
Do you like the “69” position? Do you prefer to be on top or bottom?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
12- What’s your favorite food? What’s your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
19- Do/have you smoked? What do you prefer? How often?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
14- What is an embarrassing moment in your life? How about your most embarrassing?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
If you win, what will you make them do?
53~ How much can you tell me about the one thing you are most passionate about?
(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…)
28- What are some things that people do that irritate you?
80~ Share your top three fantasies/desires. (Be detailed) 😊
22- What is your favorite childhood memory? What is your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
7-What do I do in bed that drives you wild? How about, what turns you off?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
65~ Describe the best orgasm you’ve ever had? Care to share?
Teacher/Student Stranger/One Night Stand
81~ Do you have any kinks and/or fetishes?
32- What's your greatest talent? Can I see it right now?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
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?
Do you think this brought you closer together?
1- What was your first impression of me? Has it changed?
Does the thought excite you? Care to share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
17- What’s your favorite holiday? What’s your least favorite?
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?
33- Beach or Mountains? Or is there another place to like better?
36- Do you play video games? What is your favorite? Do you a least favorite?
42~ What’s your biggest regret in life?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
83~ How do you feel about Porn?
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…
Please share Did you stop?
37- Do you like your name? If you could change it, what would you change it too?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Would you do it again, and would you rather 2 females or 2 males?
I would allow you to do it… What would you do to me?
23- What is your dream job? What was it as a child?
71~ Would you give your partner a hand or foot job? Would you receive one?
7- What are your thoughts on religion? Is there an afterlife?
18- How often do you drink alcohol? What is your favorite drink?
51~ Are you willing to play adult games with your partner?
31- If given a chance to be immortal, would you take it? Why?
19- What’s your favorite fairytale? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Do you like it when they show and tell you what they want?
48~ Do you have any siblings? Are you close to your family?
89~ Do you like taking showers together?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
52~ What are your hobbies?
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)
13- How about having a certain hair cut/style?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
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?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
6- Do you have dreams? Can you remember them? What do you usually dream about?
The Ice Breaker Questions
34- Ever been to a concert? What was your favorite? Who would you like to see?
Would /have you ever given your partner a lap dance and Striptease?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
If NO, would you ever have one? Would it be with 2 men or 2 women?
Family Relation Age Play
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Get this wrong and this could mean the end… :-) some funny, some not…
Model/Photographer Police/Criminal
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
30~ What's something unexpected that turns you on?
9- What’s your favorite season and why? What’s your least favorite?
25~ How do you feel about PDA? (Public Display of Affection)
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?
Do you watch it? What is your favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How old are you? Male or Female?
76~ Have you had a threesome? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
Master/Slave Boss/Maid
3- What Superhero or Superpower would you want to be/have?
1- What’s your favorite animal? Do you a least favorite?
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?
34~ Do you like the lights on or off during sex?
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?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
15- What's your favorite saying? What word or phrase is your least favorite?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
36~ What is your favorite time of day to have sex/make love?
5- Have you ever been hypnotized? Would you allow yourself to be?
What would you say to prove to yourself that it was really you?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Prisoner/Prison Guard Landlord/Tenant
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
4- For a pet, Cat, dog or other?
9- If you could have three wishes, what would they be? Why?
50~ How many children do you have? What are their ages?
26~ What side of the bed do you sleep on?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
45~ How do you feel about me blindfolding you? How about blindfolding me?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
18~ Who/when was your first “crush”?
3- Should Pluto still be considered a planet? 4- How about smoking?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
28~ What are some things that turn on? What is your biggest turn on?
Any that are a turn off?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
15- What bad habit do you wish you could quit? Do you have any addictions?
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
49~ How many times have you been married? Why did they end?
12- What is the weirdest thing you've ever eaten?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
10~ How many dates are necessary before you to have sex with someone?
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?
62~ Have you used adult toys?
Doctor/Nurse Stripper/Client
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
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?
14- What's your favorite dessert? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
Escort/Client Job Applicant/Hiring Manager
Can you Deep Throat? Do you like the taste of yourself?
11- How about if they like a certain sports team? 12-How about drinking too much?
60~ How important is oral sex? Do you like receiving? Do you like giving?
If you say it, I will stop, and we can talk about it when you are ready.
Will you cheat again? How can, you be sure? Define what cheating is to you.
3- What was the most surprising thing you’ve learned about me throughout our relationship?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
47~ What would be your dream job and why?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
21- What's your favorite way to spend a weekend or time off?
29- How superstitious are you?
22- Do you have any birth marks? How about scars? Care to share how you got them?
39~ What are your love languages?
92~ Have you ever had or have an STD? How many? What was it?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
61~ How willing would you be to try new sexual positions?
44~ Care to share something about yourself that no one else knows about you?
8- What's your favorite flavor of ice cream? Do you a least favorite?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
Have you ever? Care to Share?
*** Random Questions ***
3- What’s your favorite smell? Do you a least favorite?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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 is the craziest/scariest thing you've ever done?
What was the longest? What was the shortest?
How many partners have you had oral sex with? Who? 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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
5~ When you first started having sex, was it what you thought it would be?
92~ Everyone needs a “safe” word. What is yours?