What is the most interesting question you can ask to get to know someone?
Last Updated: 02.07.2025 01:28
Do you think this brought you closer together?
*** Deal Breaker Questions ***
That one or two things that made you go hmmmm, OMG or wow!
An AIDS orphan, a pastor and his frantic search for the meds that keep her alive - NPR
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
If you lose, are you willing to be their sex slave for a day, (anything goes)?
*** What’s Your Favorite…? ***
Screen Time Nightmare: How ‘Digital Pacifiers’ Are Sucking The Sanity Out Of Children - Study Finds
What is your view on sex? Meaning, When/Where/ How often/
33- Beach or Mountains? Or is there another place to like better?
25~ How do you feel about PDA? (Public Display of Affection)
A New Law of Nature Attempts to Explain the Complexity of the Universe - WIRED
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
52~ What are your hobbies?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Cosmic Dawn with Nobel Laureate John Mather - NASA (.gov)
92~ Everyone needs a “safe” word. What is yours?
Have you ever? Care to Share?
Please share Did you stop?
Maybe not best, but Sounders are most fitting MLS Club World Cup representative - Sounder at Heart
9~ How many times over your lifetime do you think you have had sex so far?
51~ What tends to bring a smile to your face?
14- What's your favorite dessert? Do you a least favorite?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
Can you Deep Throat? Do you like the taste of yourself?
Aryna Sabalenka Releases Statement Amid Backlash Over Coco Gauff Comments - Sports Illustrated
What is your favorite position? Why?
89~ Do you like taking showers together?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Elden Ring Nightreign Patch Notes Include Promised Improvements For Solo Play - GameSpot
3- Should Pluto still be considered a planet? 4- How about smoking?
How about if they talk dirty and/or call you names?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
44~ Care to share something about yourself that no one else knows about you?
Mia Goth Joins Shawn Levy’s ‘Star Wars: Starfighter’ Alongside Ryan Gosling - Variety
22- What is your favorite childhood memory? What is your least favorite?
Model/Photographer Police/Criminal
64~ When was your very first orgasm? When was your first from having sex? Care to share?
Steelers TE wants no part of Jonnu Smith trade - Behind the Steel Curtain
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
10- What is your favorite family tradition? What’s your least favorite?
Quis sed officia eum accusantium animi.
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Doctor/Nurse Stripper/Client
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
48~ Do you have any siblings? Are you close to your family?
How the Brain’s RNA Rings Are Formed - Neuroscience News
19~ Who/when was your first “heartbreak”?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
26~ What side of the bed do you sleep on?
These glowing axolotls may hold the secret to human limb regeneration - The Washington Post
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Any that are a turn off?
Nothing too Serious
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
33- If you could visit any time period, when would you pick? Please explain why?
21~ What was the best date you ever went on? What has been the worst?
9- If you could have three wishes, what would they be? Why?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
23- What is your dream job? What was it as a child?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
Over time has your thoughts on sex changed?
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?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
84~ How do you feel about reading/listening to adult stories?
71~ Would you give your partner a hand or foot job? Would you receive one?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
3- What’s your favorite smell? Do you a least favorite?
37- Do you like your name? If you could change it, what would you change it too?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
Would you ever want to be woken up with oral and/or intercourse?
If YES, was it with 2 men or 2 women? Did you enjoy it?
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?
Get this wrong and this could mean the end… :-) some funny, some not…
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
If NO, would you ever have one? Would it be with 2 men or 2 women?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
13- How about having a certain hair cut/style?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Master/Slave Boss/Maid
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?
17- What’s your favorite holiday? What’s your least favorite?
*** Random Questions ***
40~ What’s the weirdest place you’ve ever had sex?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
34~ Do you like the lights on or off during sex?
Does the thought excite you? Care to share?
Any that are a turn off?
50~ How many children do you have? What are their ages?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
21- What's your favorite way to spend a weekend or time off?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
47~ What would be your dream job and why?
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?
1~ How old were you when you had your first kiss? Who? Care to Share?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
81~ Do you have any kinks and/or fetishes?
Do you like it when they show and tell you what they want?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
15- What's your favorite saying? What word or phrase is your least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
3- What Superhero or Superpower would you want to be/have?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
62~ Have you used adult toys?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
18~ Who/when was your first “crush”?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
52~ Are you willing to make “those types” of bets with your partner?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
How well do you know me? And some of your thoughts about me
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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…
9- Is there something you’ve always wanted to ask me but you’re afraid?
*** Questions about Relationships/Past ***
Prisoner/Prison Guard Landlord/Tenant
*** Questions About Me ***
6- Do you have dreams? Can you remember them? What do you usually dream about?
83~ How do you feel about Porn?
13- What is the craziest/scariest thing you've ever done?
Do you watch it? What is your favorite?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
How many times do you think you have “made love”?
8- What are your thoughts on politics?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
* Give a rating for each one (0-100)
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?
28~ What are some things that turn on? What is your biggest turn on?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
18- How often do you drink alcohol? What is your favorite drink?
Nurse/Patient Celebrity/Fan
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What have you learned about me that was new and/or surprising?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
51~ Are you willing to play adult games with your partner?
7-What do I do in bed that drives you wild? How about, what turns you off?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
If you say it, I will stop, and we can talk about it when you are ready.
What is your favorite toy? Ever wanted to try a specific toy?
How many partners have you had oral sex with? Who? Care to Share?
60~ How important is oral sex? Do you like receiving? Do you like giving?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
Escort/Client Job Applicant/Hiring Manager
12- What’s your favorite food? What’s your least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
1- What was your first impression of me? Has it changed?
19- What’s your favorite fairytale? What’s your least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
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?
92~ Have you ever had or have an STD? How many? What was it?
34- Ever been to a concert? What was your favorite? Who would you like to see?
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?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
What do you dislike about me? I asked you to be 100% honest.
49~ How many times have you been married? Why did they end?
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?
82~ Do you have any fantasies involving Role-Playing?
39~ What are your love languages?
15- What bad habit do you wish you could quit? Do you have any addictions?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Family Relation Age Play
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
10~ How many dates are necessary before you to have sex with someone?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Would you mind if your partner watched it? How about together vs alone?
4- For a pet, Cat, dog or other?
(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…)
7- What are your thoughts on religion? Is there an afterlife?
14- What is an embarrassing moment in your life? How about your most embarrassing?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
Teacher/Student Stranger/One Night Stand
If you win, what will you make them do?
10- List 5 of your top pet peeves.
Would /have you ever given your partner a lap dance and Striptease?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
Do you like the “69” position? Do you prefer to be on top or bottom?
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?
27- What was/ is nickname? Does it have a meaning behind it?
The Ice Breaker Questions
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
11- What's your favorite restaurant? What’s your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Repairman/Lonely Wife Virgin/Experienced
Would you allow me to clean every part of your body with my soapy hands and fingers?
29- How superstitious are you?
29~ What are some things that turn you off? What is your biggest turn off?
9- What’s your favorite season and why? What’s your least favorite?
If yes, what?
17- Have you ever done drugs? Which ones? How often?
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?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
20- What’s your favorite candy? What’s your least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
You know that I will be 100% truthful, so ask.
38~ Share your most embarrassing sexual memory?
13- What’s your favorite drink? What’s your least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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…
76~ Have you had a threesome? Care to Share?
Would you read them together?
11- List at least 5 things on your bucket list. Have you done any of them already?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
32- What's your greatest talent? Can I see it right now?
5~ When you first started having sex, was it what you thought it would be?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
12- What is the weirdest thing you've ever eaten?
53~ How much can you tell me about the one thing you are most passionate about?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
What have you learned about yourself that you did not before this?
11~ Have you ever been caught by your parents or children or others while having sex?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
11- How about if they like a certain sports team? 12-How about drinking too much?
How old are you? Male or Female?
7- What if a person smells a certain way? 8- How about smoking?
What would you say to prove to yourself that it was really you?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
48~ Have you ever paid or been paid for sex?
I would allow you to do it… What would you do to me?
70~ Would/do you have/like anal sex?
19- Do/have you smoked? What do you prefer? How often?
Would you do it again, and would you rather 2 females or 2 males?
31- If given a chance to be immortal, would you take it? Why?
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 was the longest? What was the shortest?
36~ What is your favorite time of day to have sex/make love?
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?
36- Do you play video games? What is your favorite? Do you a least favorite?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
5- Have you ever been hypnotized? Would you allow yourself to be?
1- What’s your favorite animal? Do you a least favorite?
61~ How willing would you be to try new sexual positions?
2- What’s your favorite color? Do you a 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)
15~ Have you ever been “in love”? Who? Care to Share?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Do you have a favorite? Is it ok if your partner does?
65~ Describe the best orgasm you’ve ever had? Care to share?
30~ What's something unexpected that turns you on?
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…
42~ What’s your biggest regret in life?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
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?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?