What is the most interesting question you can ask to get to know someone?
Last Updated: 26.06.2025 17:01
81~ Do you have any kinks and/or fetishes?
Teacher/Student Stranger/One Night Stand
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Oregon State leaves no doubt, outslug Florida State to reach College World Series - OregonLive.com
Does the thought excite you? Care to share?
45~ How do you feel about me blindfolding you? How about blindfolding me?
3- What Superhero or Superpower would you want to be/have?
What was your biggest culture shock going to Europe?
Escort/Client Job Applicant/Hiring Manager
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
11~ Have you ever been caught by your parents or children or others while having sex?
Top Federal Reserve official promises major overhaul of US bank regulation - Financial Times
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
34- Ever been to a concert? What was your favorite? Who would you like to see?
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13~ Is there a difference between, making love, having sex, and fucking?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
48~ Have you ever paid or been paid for sex?
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?
Would you mind if your partner watched it? How about together vs alone?
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?
17- What’s your favorite holiday? What’s your least favorite?
50~ How many children do you have? What are their ages?
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5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Are there any free methods to remove only the vocals (not music) from an MP4 file?
22- What is your favorite childhood memory? What is your least favorite?
15~ Have you ever been “in love”? Who? 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?
Can you tell me something about yourself?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
39~ What are your love languages?
What is the future of artificial intelligence?
67~ Do you like it when your partner moans and/or is vocal during sex?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
Is Matt Gaetz qualified to be Attorney General of the United States?
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?
21- What's your favorite way to spend a weekend or time off?
Can you Deep Throat? Do you like the taste of yourself?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
36- Do you play video games? What is your favorite? Do you a least favorite?
Repairman/Lonely Wife Virgin/Experienced
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
26~ What side of the bed do you sleep on?
40~ What’s the weirdest place you’ve ever had sex?
Why are Indians so influenced by the Western culture, when the Indian tradition has so much to give?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
11- List at least 5 things on your bucket list. Have you done any of them already?
15- What bad habit do you wish you could quit? Do you have any addictions?
52~ Are you willing to make “those types” of bets with your partner?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Do you like it when they show and tell you what they want?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would /have you ever given your partner a lap dance and Striptease?
31- If given a chance to be immortal, would you take it? Why?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
70~ Would/do you have/like anal sex?
19- Do/have you smoked? What do you prefer? How often?
The Ice Breaker Questions
29~ What are some things that turn you off? What is your biggest turn off?
How many times do you think you have “made love”?
Family Relation Age Play
Would you read them together?
23- What is your dream job? What was it as a child?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
*** Deal Breaker Questions ***
13- What is the craziest/scariest thing you've ever done?
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)
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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…
If you say it, I will stop, and we can talk about it when you are ready.
14- What is an embarrassing moment in your life? How about your most embarrassing?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
How about if they talk dirty and/or call you names?
I would allow you to do it… What would you do to me?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
7- What are your thoughts on religion? Is there an afterlife?
8- What's your favorite flavor of ice cream? Do you a least favorite?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
What is your favorite position? Why?
Would you do it again, and would you rather 2 females or 2 males?
Would you allow me to clean every part of your body with my soapy hands and fingers?
* Give a rating for each one (0-100)
48~ Do you have any siblings? Are you close to your family?
33- Beach or Mountains? Or is there another place to like better?
13- How about having a certain hair cut/style?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
89~ Do you like taking showers together?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
How well do you know me? And some of your thoughts about me
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
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?
37- Do you like your name? If you could change it, what would you change it too?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
What have you learned about me that was new and/or surprising?
4- For a pet, Cat, dog or other?
Any that are a turn off?
Doctor/Nurse Stripper/Client
20- What’s your favorite candy? What’s your least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Get this wrong and this could mean the end… :-) some funny, some not…
80~ Share your top three fantasies/desires. (Be detailed) 😊
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
2- What’s your favorite color? Do you a least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
11- How about if they like a certain sports team? 12-How about drinking too much?
18~ Who/when was your first “crush”?
65~ Describe the best orgasm you’ve ever had? Care to share?
13- What’s your favorite drink? What’s your least favorite?
Do you think this brought you closer together?
Have you ever? Care to Share?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you like the “69” position? Do you prefer to be on top or bottom?
38~ Share your most embarrassing sexual memory?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
60~ How important is oral sex? Do you like receiving? Do you like giving?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
61~ How willing would you be to try new sexual positions?
53~ How much can you tell me about the one thing you are most passionate about?
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?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Any that are a turn off?
5~ When you first started having sex, was it what you thought it would be?
21~ What was the best date you ever went on? What has been the worst?
10~ How many dates are necessary before you to have sex with someone?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Prisoner/Prison Guard Landlord/Tenant
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
That one or two things that made you go hmmmm, OMG or wow!
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
30~ What's something unexpected that turns you on?
44~ Care to share something about yourself that no one else knows about you?
29- How superstitious are you?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
3- What’s your favorite smell? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
What is your favorite toy? Ever wanted to try a specific toy?
Do you watch it? What is your favorite?
1- What was your first impression of me? Has it changed?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
7- What if a person smells a certain way? 8- How about smoking?
*** Questions about Relationships/Past ***
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
9- If you could have three wishes, what would they be? Why?
7-What do I do in bed that drives you wild? How about, what turns you off?
25~ How do you feel about PDA? (Public Display of Affection)
14- What's your favorite dessert? Do you a least favorite?
11- What's your favorite restaurant? 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,
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? 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?
*** Questions About Me ***
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
17- Have you ever done drugs? Which ones? How often?
15- What's your favorite saying? What word or phrase is your least favorite?
19- What’s your favorite fairytale? What’s your least favorite?
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?
If yes, what?
49~ How many times have you been married? Why did they end?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
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…
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
62~ Have you used adult toys?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Model/Photographer Police/Criminal
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
28~ What are some things that turn on? What is your biggest turn on?
82~ Do you have any fantasies involving Role-Playing?
What is your view on sex? Meaning, When/Where/ How often/
84~ How do you feel about reading/listening to adult stories?
33- If you could visit any time period, when would you pick? Please explain why?
12- What is the weirdest thing you've ever eaten?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
10- What is your favorite family tradition? 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?
Please share Did you stop?
76~ Have you had a threesome? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
How old are you? Male or Female?
71~ Would you give your partner a hand or foot job? Would you receive one?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If you win, what will you make them do?
18- How often do you drink alcohol? What is your favorite drink?
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?
Would you ever want to be woken up with oral and/or intercourse?
36~ What is your favorite time of day to have sex/make love?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Over time has your thoughts on sex changed?
You know that I will be 100% truthful, so ask.
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
8- What are your thoughts on politics?
*** What’s Your Favorite…? ***
6- Do you have dreams? Can you remember them? What do you usually dream about?
Nothing too Serious
If NO, would you ever have one? Would it be with 2 men or 2 women?
(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…)
42~ What’s your biggest regret in life?
Will you cheat again? How can, you be sure? Define what cheating is to you.
22- Do you have any birth marks? How about scars? Care to share how you got them?
28- What are some things that people do that irritate you?
51~ What tends to bring a smile to your face?
Do you have a favorite? Is it ok if your partner does?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
27- What was/ is nickname? Does it have a meaning behind it?
9- What’s your favorite season and why? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
51~ Are you willing to play adult games with your partner?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
10- List 5 of your top pet peeves.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
3- Should Pluto still be considered a planet? 4- How about smoking?
12- What’s your favorite food? What’s your least favorite?
52~ What are your hobbies?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
92~ Have you ever had or have an STD? How many? What was it?
1- What’s your favorite animal? Do you a least favorite?
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?
What was the longest? What was the shortest?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
34~ Do you like the lights on or off during sex?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Master/Slave Boss/Maid
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
32- What's your greatest talent? Can I see it right now?
5- Have you ever been hypnotized? Would you allow yourself to be?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
What would you say to prove to yourself that it was really you?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
What do you dislike about me? I asked you to be 100% honest.
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
47~ What would be your dream job and why?
19~ Who/when was your first “heartbreak”?
Nurse/Patient Celebrity/Fan
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
*** Random Questions ***
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
How many partners have you had oral sex with? Who? Care to Share?
What have you learned about yourself that you did not before this?
83~ How do you feel about Porn?