What is the most interesting question you can ask to get to know someone?
Last Updated: 21.06.2025 08:38
10- What is your favorite family tradition? What’s your least favorite?
7- What are your thoughts on religion? Is there an afterlife?
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?
CNN’s Live ‘Good Night, and Good Luck’ Telecast Spurs Special Coverage - Variety
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
If YES, was it with 2 men or 2 women? Did you enjoy it?
Upcoming temporary full closure of South Academy Boulevard for widening project - KKTV
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
19~ Who/when was your first “heartbreak”?
What is your favorite underrated movie and why? What makes it underrated? How did you find it?
1- What was your first impression of me? Has it changed?
40~ What’s the weirdest place you’ve ever had sex?
What was the longest? What was the shortest?
Watch: Moment crowd boos and cheers Trump at Kennedy Center - BBC
5~ When you first started having sex, was it what you thought it would be?
15- What bad habit do you wish you could quit? Do you have any addictions?
32- What's your greatest talent? Can I see it right now?
If you win, what will you make them do?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Can you recommend a simple song with an awesome solo? What makes the solo stand out?
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…
8- What are your thoughts on politics?
36- Do you play video games? What is your favorite? Do you a least favorite?
Andy Bogard's Fatal Fury: City of the Wolves gameplay trailer revealed, releases June 24 - EventHubs
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
15~ Have you ever been “in love”? Who? Care to Share?
8- What's your favorite flavor of ice cream? Do you a least favorite?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
3- What’s your favorite smell? Do you a least favorite?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
It’s back! Massive $400 price drop now live on 2TB Space Black M4 iPad Pro at Amazon - 9to5Toys
Family Relation Age Play
1- What’s your favorite animal? Do you a least favorite?
What have you learned about me that was new and/or surprising?
Where you live may affect your risk of dementia, UCSF study finds - San Francisco Chronicle
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
3- What Superhero or Superpower would you want to be/have?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
What is the best audio editing software for removing background noise and voices from videos?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
How about if they talk dirty and/or call you names?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
What is the difference in effectiveness between an infrared sauna blanket and a regular one?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
61~ How willing would you be to try new sexual positions?
Repairman/Lonely Wife Virgin/Experienced
Why are Capri cigarettes so expensive?
Please share Did you stop?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
31- If given a chance to be immortal, would you take it? Why?
What are some hard rock or heavy metal bands that are overrated?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
If yes, what?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
9- If you could have three wishes, what would they be? Why?
45~ How do you feel about me blindfolding you? How about blindfolding me?
92~ Have you ever had or have an STD? How many? What was it?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
22- Do you have any birth marks? How about scars? Care to share how you got them?
How many partners have you had oral sex with? Who? Care to Share?
How old are you? Male or Female?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
48~ Do you have any siblings? Are you close to your family?
19- Do/have you smoked? What do you prefer? How often?
34- Ever been to a concert? What was your favorite? Who would you like to see?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Have you ever? 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.
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
What do you dislike about me? I asked you to be 100% honest.
23- What is your dream job? What was it as a child?
7-What do I do in bed that drives you wild? How about, what turns you off?
13- What is the craziest/scariest thing you've ever done?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
You know that I will be 100% truthful, so ask.
I would allow you to do it… What would you do to me?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Will you cheat again? How can, you be sure? Define what cheating is to you.
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Would you do it again, and would you rather 2 females or 2 males?
28- What are some things that people do that irritate you?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
60~ How important is oral sex? Do you like receiving? Do you like giving?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
20- What’s your favorite candy? What’s your least favorite?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
Nothing too Serious
22- What is your favorite childhood memory? What is your least favorite?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
11- What's your favorite restaurant? 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?
1~ How old were you when you had your first kiss? Who? Care to Share?
47~ What would be your dream job and why?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Would /have you ever given your partner a lap dance and Striptease?
7- What if a person smells a certain way? 8- How about smoking?
Would you ever want to be woken up with oral and/or intercourse?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
13- What’s your favorite drink? What’s your least favorite?
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)
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
10~ How many dates are necessary before you to have sex with someone?
44~ Care to share something about yourself that no one else knows about you?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
2- What’s your favorite color? Do you a least favorite?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
9- What’s your favorite season and why? What’s your least favorite?
83~ How do you feel about Porn?
11~ Have you ever been caught by your parents or children or others while having sex?
Master/Slave Boss/Maid
Do you watch it? What is your favorite?
21- What's your favorite way to spend a weekend or time off?
12- What is the weirdest thing you've ever eaten?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Will you kiss after your partner has gone down on you? Swallow or spit semen?
19- What’s your favorite fairytale? What’s your least favorite?
Does the thought excite you? Care to share?
48~ Have you ever paid or been paid for sex?
71~ Would you give your partner a hand or foot job? Would you receive one?
*** Random Questions ***
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
5- Have you ever been hypnotized? Would you allow yourself to be?
26~ What side of the bed do you sleep on?
Do you think this brought you closer together?
Would you mind if your partner watched it? How about together vs alone?
37- Do you like your name? If you could change it, what would you change it too?
*** Questions About Me ***
What is your favorite toy? Ever wanted to try a specific toy?
84~ How do you feel about reading/listening to adult stories?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How well do you know me? And some of your thoughts about me
12- What’s your favorite food? What’s your least favorite?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
Would you allow me to clean every part of your body with my soapy hands and fingers?
34~ Do you like the lights on or off during sex?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
30~ What's something unexpected that turns you on?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
13- How about having a certain hair cut/style?
If NO, would you ever have one? Would it be with 2 men or 2 women?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
14- What is an embarrassing moment in your life? How about your most embarrassing?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
3- Should Pluto still be considered a planet? 4- How about smoking?
Escort/Client Job Applicant/Hiring Manager
Teacher/Student Stranger/One Night Stand
6- Do you have dreams? Can you remember them? What do you usually dream about?
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 many times do you think you have “made love”?
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 are your expectations in a relationship? (I know a very big question, take your time)
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
What is your view on sex? Meaning, When/Where/ How often/
22~ What is the best pickup line anyone has ever used on you? What was the worst?
27- What was/ is nickname? Does it have a meaning behind it?
49~ How many times have you been married? Why did they end?
53~ How much can you tell me about the one thing you are most passionate about?
36~ What is your favorite time of day to have sex/make love?
Model/Photographer Police/Criminal
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
What is your favorite position? Why?
Would you read them together?
18~ Who/when was your first “crush”?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
76~ Have you had a threesome? Care to Share?
If you say it, I will stop, and we can talk about it when you are ready.
Get this wrong and this could mean the end… :-) some funny, some not…
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,
39~ What are your love languages?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
62~ Have you used adult toys?
52~ What are your hobbies?
11- How about if they like a certain sports team? 12-How about drinking too much?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
What have you learned about yourself that you did not before this?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
50~ How many children do you have? What are their ages?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
51~ What tends to bring a smile to your face?
*** What’s Your Favorite…? ***
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
10- List 5 of your top pet peeves.
81~ Do you have any kinks and/or fetishes?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
14- What's your favorite dessert? Do you a least favorite?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Nurse/Patient Celebrity/Fan
65~ Describe the best orgasm you’ve ever had? Care to share?
89~ Do you like taking showers together?
Over time has your thoughts on sex changed?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
11- List at least 5 things on your bucket list. Have you done any of them already?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
70~ Would/do you have/like anal sex?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
92~ Everyone needs a “safe” word. What is yours?
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?
28~ What are some things that turn on? What is your biggest turn on?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Can you Deep Throat? Do you like the taste of yourself?
9- Is there something you’ve always wanted to ask me but you’re afraid?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
9~ How many times over your lifetime do you think you have had sex so far?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
33- If you could visit any time period, when would you pick? Please explain why?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
4- For a pet, Cat, dog or other?
*** Questions about Relationships/Past ***
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Prisoner/Prison Guard Landlord/Tenant
What’s the longest time you gone without having sex, after, having it? How much time between the others?
51~ Are you willing to play adult games with your partner?
That one or two things that made you go hmmmm, OMG or wow!
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
17- Have you ever done drugs? Which ones? How often?
29~ What are some things that turn you off? What is your biggest turn off?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
*** Deal Breaker Questions ***
82~ Do you have any fantasies involving Role-Playing?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
13~ Is there a difference between, making love, having sex, and fucking?
* Give a rating for each one (0-100)
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?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
25~ How do you feel about PDA? (Public Display of Affection)
The Ice Breaker Questions
Doctor/Nurse Stripper/Client
49~ If you could, would you want to be the opposite sex for a day, week, or year?
67~ Do you like it when your partner moans and/or is vocal during sex?
29- How superstitious are you?
17- What’s your favorite holiday? What’s your least favorite?
What would you say to prove to yourself that it was really you?
15- What's your favorite saying? What word or phrase is your least favorite?
Do you have a favorite? Is it ok if your partner does?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
21~ What was the best date you ever went on? What has been the worst?
Do you like the “69” position? Do you prefer to be on top or bottom?
Do you like it when they show and tell you what they want?
(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…)
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?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Any that are a turn off?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
33- Beach or Mountains? Or is there another place to like better?
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?
38~ Share your most embarrassing sexual memory?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
18- How often do you drink alcohol? What is your favorite drink?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
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…
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?
42~ What’s your biggest regret in life?
Any that are a turn off?