What is the most interesting question you can ask to get to know someone?
Last Updated: 24.06.2025 03:06
28- What are some things that people do that irritate you?
52~ Are you willing to make “those types” of bets with your partner?
Will you cheat again? How can, you be sure? Define what cheating is to you.
The Biggest Pokémon Card Crashers And Climbers This Week - June 2 - IGN
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Would you do it again, and would you rather 2 females or 2 males?
Your Apple CarPlay is getting a big update: 3 useful features coming with iOS 26 - ZDNet
51~ What tends to bring a smile to your face?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
3- What Superhero or Superpower would you want to be/have?
Why did McLaren hope that the Ferrari pair would pit twice during the Italian Grand Prix?
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?
5- Have you ever been hypnotized? Would you allow yourself to be?
62~ Have you used adult toys?
2- What’s your favorite color? Do you a least favorite?
How many times do you think you have “made love”?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
How to protect yourself from wildfire smoke and poor air quality - The Washington Post
How many partners have you had oral sex with? Who? Care to Share?
Doctor/Nurse Stripper/Client
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?
Steam is finally adding native support for Macs with Apple Silicon - The Verge
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
67~ Do you like it when your partner moans and/or is vocal during sex?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Does the thought excite you? Care to share?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
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?
You know that I will be 100% truthful, so ask.
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
33- If you could visit any time period, when would you pick? Please explain why?
What is the most inappropriate experience you have had with a friend's daughter?
9~ How many times over your lifetime do you think you have had sex so far?
18~ Who/when was your first “crush”?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Why do wives cheat with black guys?
39~ What are your love languages?
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,
Would /have you ever given your partner a lap dance and Striptease?
19~ Who/when was your first “heartbreak”?
30~ What's something unexpected that turns you on?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
Do you like the “69” position? Do you prefer to be on top or bottom?
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…
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
The Ice Breaker Questions
Nothing too Serious
11- What's your favorite restaurant? What’s your least favorite?
How well do you know me? And some of your thoughts about me
*** Deal Breaker Questions ***
25~ How do you feel about PDA? (Public Display of Affection)
51~ Are you willing to play adult games with your partner?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
Do you have a favorite? Is it ok if your partner does?
71~ Would you give your partner a hand or foot job? Would you receive one?
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?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
7-What do I do in bed that drives you wild? How about, what turns you off?
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
48~ Do you have any siblings? Are you close to your family?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
82~ Do you have any fantasies involving Role-Playing?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
18- What’s your favorite way to relax after a long day? What’s your least favorite?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
20- What’s your favorite candy? What’s your least favorite?
26~ What side of the bed do you sleep on?
21- What's your favorite way to spend a weekend or time off?
65~ Describe the best orgasm you’ve ever had? Care to share?
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?
(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…)
89~ Do you like taking showers together?
13- What is the craziest/scariest thing you've ever done?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
*** Questions About Me ***
What is your favorite toy? Ever wanted to try a specific toy?
Model/Photographer Police/Criminal
33- Beach or Mountains? Or is there another place to like better?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
92~ Have you ever had or have an STD? How many? What was it?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
How about if they talk dirty and/or call you names?
What have you learned about yourself that you did not before this?
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?
37- Do you like your name? If you could change it, what would you change it too?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
4- For a pet, Cat, dog or other?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Master/Slave Boss/Maid
If you win, what will you make them do?
61~ How willing would you be to try new sexual positions?
19- What’s your favorite fairytale? What’s your least favorite?
28~ What are some things that turn on? What is your biggest turn on?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
Do you watch it? What is your favorite?
10~ How many dates are necessary before you to have sex with someone?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What would you say to prove to yourself that it was really you?
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?
17- What’s your favorite holiday? What’s your least favorite?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
If YES, was it with 2 men or 2 women? Did you enjoy it?
That one or two things that made you go hmmmm, OMG or wow!
50~ How many children do you have? What are their ages?
11~ Have you ever been caught by your parents or children or others while having sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
40~ What’s the weirdest place you’ve ever had sex?
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)
21~ What was the best date you ever went on? What has been the worst?
If NO, would you ever have one? Would it be with 2 men or 2 women?
*** Random Questions ***
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…
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
Get this wrong and this could mean the end… :-) some funny, some not…
Would you allow me to clean every part of your body with my soapy hands and fingers?
29~ What are some things that turn you off? What is your biggest turn off?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
3- What’s your favorite smell? Do you a least favorite?
44~ Care to share something about yourself that no one else knows about you?
15~ Have you ever been “in love”? Who? Care to Share?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
10- List 5 of your top pet peeves.
15- What bad habit do you wish you could quit? Do you have any addictions?
6- Do you have dreams? Can you remember them? What do you usually dream about?
34- Ever been to a concert? What was your favorite? Who would you like to see?
Any that are a turn off?
11- List at least 5 things on your bucket list. Have you done any of them already?
If yes, what?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
Teacher/Student Stranger/One Night Stand
Would you ever want to be woken up with oral and/or intercourse?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
38~ Share your most embarrassing sexual memory?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
If you say it, I will stop, and we can talk about it when you are ready.
22- What is your favorite childhood memory? What is your least favorite?
Do you like it when they show and tell you what they want?
What is your view on sex? Meaning, When/Where/ How often/
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
36- Do you play video games? What is your favorite? Do you a least favorite?
29- How superstitious are you?
52~ What are your hobbies?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
Prisoner/Prison Guard Landlord/Tenant
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
42~ What’s your biggest regret in life?
Nurse/Patient Celebrity/Fan
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
22- Do you have any birth marks? How about scars? Care to share how you got them?
9- What’s your favorite season and why? What’s your least favorite?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
81~ Do you have any kinks and/or fetishes?
48~ Have you ever paid or been paid for sex?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
1- What was your first impression of me? Has it changed?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
Would you mind if your partner watched it? How about together vs alone?
9- If you could have three wishes, what would they be? Why?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
15- What's your favorite saying? What word or phrase is your least favorite?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
What was the longest? What was the shortest?
27- What was/ is nickname? Does it have a meaning behind it?
32- What's your greatest talent? Can I see it right now?
23- What is your dream job? What was it as a child?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
1~ How old were you when you had your first kiss? Who? Care to Share?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
49~ How many times have you been married? Why did they end?
11- How about if they like a certain sports team? 12-How about drinking too much?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
7- What if a person smells a certain way? 8- How about smoking?
What have you learned about me that was new and/or surprising?
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)
8- What are your thoughts on politics?
80~ Share your top three fantasies/desires. (Be detailed) 😊
47~ What would be your dream job and why?
12- What is the weirdest thing you've ever eaten?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
How old are you? Male or Female?
17- Have you ever done drugs? Which ones? How often?
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?
I would allow you to do it… What would you do to me?
19- Do/have you smoked? What do you prefer? How often?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
31- If given a chance to be immortal, would you take it? Why?
14- What's your favorite dessert? Do you a least favorite?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
1- What’s your favorite animal? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
18- How often do you drink alcohol? What is your favorite drink?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
9- Is there something you’ve always wanted to ask me but you’re afraid?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
53~ How much can you tell me about the one thing you are most passionate about?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
12- What’s your favorite food? What’s your least favorite?
* Give a rating for each one (0-100)
10- What is your favorite family tradition? What’s your least favorite?
13- What’s your favorite drink? What’s your least favorite?
Would you read them together?
Any that are a turn off?
34~ Do you like the lights on or off during sex?
What do you dislike about me? I asked you to be 100% honest.
3- Should Pluto still be considered a planet? 4- How about smoking?
Have you ever? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
Please share Did you stop?
70~ Would/do you have/like anal sex?
Do you think this brought you closer together?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
84~ How do you feel about reading/listening to adult stories?
5~ When you first started having sex, was it what you thought it would be?
Over time has your thoughts on sex changed?
45~ How do you feel about me blindfolding you? How about blindfolding me?
92~ Everyone needs a “safe” word. What is yours?
Can you Deep Throat? Do you like the taste of yourself?
*** Questions about Relationships/Past ***
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
36~ What is your favorite time of day to have sex/make love?
What is your favorite position? Why?
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?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Family Relation Age Play
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
13- How about having a certain hair cut/style?
Repairman/Lonely Wife Virgin/Experienced
60~ How important is oral sex? Do you like receiving? Do you like giving?
76~ Have you had a threesome? Care to Share?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
13~ Is there a difference between, making love, having sex, and fucking?
*** What’s Your Favorite…? ***
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…