What is the most interesting question you can ask to get to know someone?
Last Updated: 28.06.2025 06:02
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Do you like it when they show and tell you what they want?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
Could This Diet Be the Key to Preventing Alzheimer's and Dementia? - bestlifeonline.com
10- What is your favorite family tradition? 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.
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?
Solar Storms Are Pushing Elon Musk’s Satellites Back to Earth - Gizmodo
13- What’s your favorite drink? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Will you cheat again? How can, you be sure? Define what cheating is to you.
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
Do you feel uncomfortable when you come across cross dressers?
11- List at least 5 things on your bucket list. Have you done any of them already?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
47~ What would be your dream job and why?
Ask Ethan: What are the "first stars" in the Universe? - Big Think
Would you allow me to clean every part of your body with my soapy hands and fingers?
53~ How much can you tell me about the one thing you are most passionate about?
Would /have you ever given your partner a lap dance and Striptease?
What is your favorite toy? Ever wanted to try a specific toy?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
* Give a rating for each one (0-100)
Order of selection for 2025 NHL Draft - NHL.com
38~ Share your most embarrassing sexual memory?
(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…)
19- Do/have you smoked? What do you prefer? How often?
Trump airs frustrations with Xi and Jerome Powell over elusive economic goals - NBC News
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
What was the longest? What was the shortest?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Microsoft Confirms Windows 11 Automatic Deletions: Take Action Now To Protect Yourself - Forbes
49~ How many times have you been married? Why did they end?
48~ Have you ever paid or been paid for sex?
1~ How old were you when you had your first kiss? Who? Care to Share?
Which is the most liked web series in India?
15- What bad habit do you wish you could quit? Do you have any addictions?
42~ What’s your biggest regret in life?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
James Webb Space Telescope unveils fiery origins of a distant, hellish exoplanet - Space
18- How often do you drink alcohol? What is your favorite drink?
Have you ever? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Which K-pop idol has a good fashion sense in your opinion?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
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?
What have you learned about yourself that you did not before this?
Escort/Client Job Applicant/Hiring Manager
9- Is there something you’ve always wanted to ask me but you’re afraid?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
17- What’s your favorite holiday? What’s your least favorite?
These glowing axolotls may hold the secret to human limb regeneration - The Washington Post
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
25~ How do you feel about PDA? (Public Display of Affection)
What do you dislike about me? I asked you to be 100% honest.
22- Do you have any birth marks? How about scars? Care to share how you got them?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
64~ When was your very first orgasm? When was your first from having sex? Care to share?
13- How about having a certain hair cut/style?
Do you think this brought you closer together?
Over time has your thoughts on sex changed?
5~ When you first started having sex, was it what you thought it would be?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
34~ Do you like the lights on or off during sex?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Does the thought excite you? Care to share?
The Ice Breaker Questions
41~ Are there moments in your past that you would want to change? Please share 3 of them.
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
18~ Who/when was your first “crush”?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
89~ Do you like taking showers together?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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…
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
84~ How do you feel about reading/listening to adult stories?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
15~ Have you ever been “in love”? Who? Care to Share?
9- What’s your favorite season and why? What’s your least favorite?
3- What’s your favorite smell? Do you a least favorite?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
Please share Did you stop?
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?
48~ Do you have any siblings? Are you close to your family?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
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?
That one or two things that made you go hmmmm, OMG or wow!
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
3- What Superhero or Superpower would you want to be/have?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
10~ How many dates are necessary before you to have sex with someone?
37- Do you like your name? If you could change it, what would you change it too?
Master/Slave Boss/Maid
How about if they talk dirty and/or call you names?
65~ Describe the best orgasm you’ve ever had? Care to share?
30~ What's something unexpected that turns you on?
92~ Everyone needs a “safe” word. What is yours?
*** Deal Breaker Questions ***
17- Have you ever done drugs? Which ones? How often?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
*** Questions about Relationships/Past ***
Would you do it again, and would you rather 2 females or 2 males?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
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…
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
31- If given a chance to be immortal, would you take it? Why?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
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?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How old are you? Male or Female?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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,
What have you learned about me that was new and/or surprising?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
1- What was your first impression of me? Has it changed?
51~ What tends to bring a smile to your face?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
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?
8- What are your thoughts on politics?
Do you like the “69” position? Do you prefer to be on top or bottom?
Teacher/Student Stranger/One Night Stand
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
40~ What’s the weirdest place you’ve ever had sex?
8- What's your favorite flavor of ice cream? Do you a least favorite?
You know that I will be 100% truthful, so ask.
52~ What are your hobbies?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
14- What is an embarrassing moment in your life? How about your most embarrassing?
Prisoner/Prison Guard Landlord/Tenant
Doctor/Nurse Stripper/Client
35- Do you like playing board or cards game? What is your favorite? 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?
52~ Are you willing to make “those types” of bets with your partner?
21- What's your favorite way to spend a weekend or time off?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
50~ How many children do you have? What are their ages?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
39~ What are your love languages?
If you win, what will you make them do?
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?
20- What’s your favorite candy? What’s your least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
19- What’s your favorite fairytale? What’s your least favorite?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
83~ How do you feel about Porn?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
13- What is the craziest/scariest thing you've ever done?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
29- How superstitious are you?
33- Beach or Mountains? Or is there another place to like better?
81~ Do you have any kinks and/or fetishes?
Would you mind if your partner watched it? How about together vs alone?
26~ What side of the bed do you sleep on?
5- Have you ever been hypnotized? Would you allow yourself to be?
19~ Who/when was your first “heartbreak”?
1- What’s your favorite animal? Do you a least favorite?
Would you read them together?
If YES, was it with 2 men or 2 women? Did you enjoy it?
9- If you could have three wishes, what would they be? Why?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
27- What was/ is nickname? Does it have a meaning behind it?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
36- Do you play video games? What is your favorite? Do you a least favorite?
76~ Have you had a threesome? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
92~ Have you ever had or have an STD? How many? What was it?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Do you watch it? What is your favorite?
10- List 5 of your top pet peeves.
Any that are a turn off?
82~ Do you have any fantasies involving Role-Playing?
60~ How important is oral sex? Do you like receiving? Do you like giving?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
28~ What are some things that turn on? What is your biggest turn on?
22- What is your favorite childhood memory? What is your least favorite?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
45~ How do you feel about me blindfolding you? How about blindfolding me?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
Any that are a turn off?
Can you Deep Throat? Do you like the taste of yourself?
11~ Have you ever been caught by your parents or children or others while having sex?
If NO, would you ever have one? Would it be with 2 men or 2 women?
3- Should Pluto still be considered a planet? 4- How about smoking?
Get this wrong and this could mean the end… :-) some funny, some not…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
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?
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?
33- If you could visit any time period, when would you pick? Please explain why?
14- What's your favorite dessert? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
28- What are some things that people do that irritate you?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
32- What's your greatest talent? Can I see it right now?
What is your view on sex? Meaning, When/Where/ How often/
7- What if a person smells a certain way? 8- How about smoking?
Nothing too Serious
How many partners have you had oral sex with? Who? Care to Share?
23- What is your dream job? What was it as a child?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
51~ Are you willing to play adult games with your partner?
If yes, what?
70~ Would/do you have/like anal sex?
2- What’s your favorite color? 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?
62~ Have you used adult toys?
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)
*** Questions About Me ***
Repairman/Lonely Wife Virgin/Experienced
36~ What is your favorite time of day to have sex/make love?
13~ Is there a difference between, making love, having sex, and fucking?
15- What's your favorite saying? What word or phrase is your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
Do you have a favorite? Is it ok if your partner does?
*** Random Questions ***
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
21~ What was the best date you ever went on? What has been the worst?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
How many times do you think you have “made love”?
12- What’s your favorite food? What’s your least favorite?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
How well do you know me? And some of your thoughts about me
Nurse/Patient Celebrity/Fan
71~ Would you give your partner a hand or foot job? Would you receive one?
9~ How many times over your lifetime do you think you have had sex so far?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
61~ How willing would you be to try new sexual positions?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
7-What do I do in bed that drives you wild? How about, what turns you off?
Model/Photographer Police/Criminal
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
Family Relation Age Play
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
12- What is the weirdest thing you've ever eaten?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
4- For a pet, Cat, dog or other?
6- Do you have dreams? Can you remember them? What do you usually dream about?
7- What are your thoughts on religion? Is there an afterlife?
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?
*** What’s Your Favorite…? ***
80~ Share your top three fantasies/desires. (Be detailed) 😊
I would allow you to do it… What would you do to me?
What is your favorite position? Why?
If you say it, I will stop, and we can talk about it when you are ready.
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?