What is the most interesting question you can ask to get to know someone?
11.06.2025 06:01
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
10~ How many dates are necessary before you to have sex with someone?
Would /have you ever given your partner a lap dance and Striptease?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
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?
What is the dirtiest thing you have witnessed your wife do?
You know that I will be 100% truthful, so ask.
How many times do you think you have “made love”?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
˗ˋˏ ♡ ˎˊ˗ NEW WOMAN - analysis ˗ˋˏ ♡ ˎˊ˗
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
51~ What tends to bring a smile to your face?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
15- What bad habit do you wish you could quit? Do you have any addictions?
Would you do it again, and would you rather 2 females or 2 males?
What is an easy way to get your driver's license?
If YES, was it with 2 men or 2 women? Did you enjoy it?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Escort/Client Job Applicant/Hiring Manager
Speech by Governor Kugler on the economic outlook and monetary policy - Federal Reserve Board (.gov)
18~ Who/when was your first “crush”?
71~ Would you give your partner a hand or foot job? Would you receive one?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
What was the longest? What was the shortest?
23- What is your dream job? What was it as a child?
Physicists Unveil New Quantum Super Material That Could Revolutionize Electronics - SciTechDaily
6- What’s your favorite TV series? Do you have a favorite genre? Do you a 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?
Would you ever want to be woken up with oral and/or intercourse?
Which Shakespeare words have completely changed meaning in modern English?
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…
What’s the longest time you gone without having sex, after, having it? How much time between the others?
14- What's your favorite dessert? Do you a least favorite?
Which current F1 drivers should switch teams based on historical patterns?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
81~ Do you have any kinks and/or fetishes?
CNN’s Live ‘Good Night, and Good Luck’ Telecast Spurs Special Coverage - Variety
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
* Give a rating for each one (0-100)
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
62~ Have you used adult toys?
Will you cheat again? How can, you be sure? Define what cheating is to you.
*** Deal Breaker Questions ***
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
13- What is the craziest/scariest thing you've ever done?
34~ Do you like the lights on or off during sex?
25~ How do you feel about PDA? (Public Display of Affection)
26~ What side of the bed do you sleep on?
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?
Doctor/Nurse Stripper/Client
52~ Are you willing to make “those types” of bets with your partner?
33- If you could visit any time period, when would you pick? Please explain why?
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?
7- What are your thoughts on religion? Is there an afterlife?
Family Relation Age Play
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you shave/trim your pubic hair? For you guys do you shave your balls?
65~ Describe the best orgasm you’ve ever had? Care to share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
13- How about having a certain hair cut/style?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
32- What's your greatest talent? Can I see it right now?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
(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?
29- How superstitious are you?
What would you say to prove to yourself that it was really you?
Master/Slave Boss/Maid
What is your favorite position? Why?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
22- Do you have any birth marks? How about scars? Care to share how you got them?
7- What if a person smells a certain way? 8- How about smoking?
3- What Superhero or Superpower would you want to be/have?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
*** Questions About Me ***
What is your favorite toy? Ever wanted to try a specific toy?
76~ Have you had a threesome? Care to Share?
Would you mind if your partner watched it? How about together vs alone?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
39~ What are your love languages?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you watch it? What is your favorite?
36~ What is your favorite time of day to have sex/make love?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
28~ What are some things that turn on? What is your biggest turn on?
Nurse/Patient Celebrity/Fan
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
21~ What was the best date you ever went on? What has been the worst?
Prisoner/Prison Guard Landlord/Tenant
13~ Is there a difference between, making love, having sex, and fucking?
Over time has your thoughts on sex changed?
5- Have you ever been hypnotized? Would you allow yourself to be?
33- Beach or Mountains? Or is there another place to like better?
21- What's your favorite way to spend a weekend or time off?
82~ Do you have any fantasies involving Role-Playing?
84~ How do you feel about reading/listening to adult stories?
8- What are your thoughts on politics?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
80~ Share your top three fantasies/desires. (Be detailed) 😊
9- If you could have three wishes, what would they be? Why?
(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…)
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?
Have you ever? Care to Share?
12- What’s your favorite food? What’s your 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.
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
92~ Have you ever had or have an STD? How many? What was it?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
52~ What are your hobbies?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
How many partners have you had oral sex with? Who? Care to Share?
Do you like it when they show and tell you what they want?
The Ice Breaker Questions
11- What's your favorite restaurant? What’s your least favorite?
30~ What's something unexpected that turns you on?
Would you read them together?
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?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
19- What’s your favorite fairytale? What’s your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
17- Have you ever done drugs? Which ones? How often?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
6- Do you have dreams? Can you remember them? What do you usually dream about?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Teacher/Student Stranger/One Night Stand
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
Do you think this brought you closer together?
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)
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Does the thought excite you? Care to share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Model/Photographer Police/Criminal
7- What’s your favorite book? Do you have a favorite genre? 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?
42~ What’s your biggest regret in life?
*** Random Questions ***
46~ Have you ever used furniture, or other types of things to aid you while having sex?
37- Do you like your name? If you could change it, what would you change it too?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
20- What’s your favorite candy? What’s your least favorite?
Any that are a turn off?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Do you like the “69” position? Do you prefer to be on top or bottom?
1- What was your first impression of me? Has it changed?
If NO, would you ever have one? Would it be with 2 men or 2 women?
3- What’s your favorite smell? Do you a least favorite?
53~ How much can you tell me about the one thing you are most passionate about?
What have you learned about yourself that you did not before this?
15~ Have you ever been “in love”? Who? Care to Share?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
19~ Who/when was your first “heartbreak”?
22- What is your favorite childhood memory? What is your least favorite?
*** Questions about Relationships/Past ***
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
47~ What would be your dream job and why?
70~ Would/do you have/like anal sex?
What have you learned about me that was new and/or surprising?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
11~ Have you ever been caught by your parents or children or others while having sex?
50~ How many children do you have? What are their ages?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
What do you dislike about me? I asked you to be 100% honest.
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
83~ How do you feel about Porn?
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)
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Repairman/Lonely Wife Virgin/Experienced
That one or two things that made you go hmmmm, OMG or wow!
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
12- What is the weirdest thing you've ever eaten?
5~ When you first started having sex, was it what you thought it would be?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
11- How about if they like a certain sports team? 12-How about drinking too much?
What is your view on sex? Meaning, When/Where/ How often/
27- What was/ is nickname? Does it have a meaning behind it?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
9- Is there something you’ve always wanted to ask me but you’re afraid?
44~ Care to share something about yourself that no one else knows about you?
29~ What are some things that turn you off? What is your biggest turn off?
67~ Do you like it when your partner moans and/or is vocal during sex?
4- For a pet, Cat, dog or other?
Do you have a favorite? Is it ok if your partner does?
Any that are a turn off?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched 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?
48~ Have you ever paid or been paid for sex?
I would allow you to do it… What would you do to me?
10- What is your favorite family tradition? What’s your least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
1~ How old were you when you had your first kiss? Who? Care to Share?
Please share Did you stop?
61~ How willing would you be to try new sexual positions?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
13- What’s your favorite drink? What’s your least favorite?
Get this wrong and this could mean the end… :-) some funny, some not…
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
1- What’s your favorite animal? Do you a least favorite?
89~ Do you like taking showers together?
How old are you? Male or Female?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
49~ How many times have you been married? Why did they end?
Nothing too Serious
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
If you win, what will you make them do?
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?
15- What's your favorite saying? What word or phrase is your least favorite?
51~ Are you willing to play adult games with your partner?
11- List at least 5 things on your bucket list. Have you done any of them already?
92~ Everyone needs a “safe” word. What is yours?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
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,
How about if they talk dirty and/or call you names?
48~ Do you have any siblings? Are you close to your family?
8- What's your favorite flavor of ice cream? Do you a least favorite?
Can you Deep Throat? Do you like the taste of yourself?
*** What’s Your Favorite…? ***
How well do you know me? And some of your thoughts about me
10- List 5 of your top pet peeves.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
36- Do you play video games? What is your favorite? Do you a least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
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~ 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?
9~ How many times over your lifetime do you think you have had sex so far?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
14- What is an embarrassing moment in your life? How about your most embarrassing?
31- If given a chance to be immortal, would you take it? Why?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Would you allow me to clean every part of your body with my soapy hands and fingers?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
9- What’s your favorite season and why? What’s your least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
2- What’s your favorite color? Do you a least favorite?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
28- What are some things that people do that irritate you?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
19- Do/have you smoked? What do you prefer? How often?
If yes, what?
38~ Share your most embarrassing sexual memory?
17- What’s your favorite holiday? What’s your least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?