What is the most interesting question you can ask to get to know someone?
Last Updated: 22.06.2025 02:27
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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?
81~ Do you have any kinks and/or fetishes?
How terrible are we at making future predictions of like technology?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Prisoner/Prison Guard Landlord/Tenant
Will you kiss after your partner has gone down on you? Swallow or spit semen?
Do you think there will ever be peace in the Middle East as long as Israel exists?
Will you cheat again? How can, you be sure? Define what cheating is to you.
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
2- What’s your favorite color? Do you a least favorite?
Rune Factory: Guardians of Azuma Review - RPGFan
25~ How do you feel about PDA? (Public Display of Affection)
27- What was/ is nickname? Does it have a meaning behind it?
1~ How old were you when you had your first kiss? Who? Care to Share?
Willi Castro homers twice, Royce Lewis ends skid as Twins crush Athletics - Sports Illustrated
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
What are the most outrageous violations of restaurant buffet etiquette have you seen?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
21~ What was the best date you ever went on? What has been the worst?
11~ Have you ever been caught by your parents or children or others while having sex?
Why does a straight man like anal penetration?
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?
53~ How much can you tell me about the one thing you are most passionate about?
*** Questions About Me ***
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
9- Is there something you’ve always wanted to ask me but you’re afraid?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Escort/Client Job Applicant/Hiring Manager
33- If you could visit any time period, when would you pick? Please explain why?
How can I use AI to create custom music to accompany my vocal song or poetry?
Over time has your thoughts on sex changed?
Any that are a turn off?
52~ What are your hobbies?
How is bestiality wrong, but killing animals for sport or trophies is considered okay?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Would you mind if your partner watched it? How about together vs alone?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
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?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
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…
3- Should Pluto still be considered a planet? 4- How about smoking?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
I would allow you to do it… What would you do to me?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
48~ Have you ever paid or been paid for sex?
39~ What are your love languages?
11- List at least 5 things on your bucket list. Have you done any of them already?
76~ Have you had a threesome? Care to Share?
70~ Would/do you have/like anal sex?
28~ What are some things that turn on? What is your biggest turn on?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3- What Superhero or Superpower would you want to be/have?
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?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
20- What’s your favorite candy? What’s your least favorite?
Teacher/Student Stranger/One Night Stand
67~ Do you like it when your partner moans and/or is vocal during sex?
Nothing too Serious
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
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?
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?
Family Relation Age Play
34- Ever been to a concert? What was your favorite? Who would you like to see?
Do you like the “69” position? Do you prefer to be on top or bottom?
44~ Care to share something about yourself that no one else knows about you?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Do you watch it? What is your favorite?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
10~ How many dates are necessary before you to have sex with someone?
Have you ever? Care to Share?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
22- Do you have any birth marks? How about scars? Care to share how you got them?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
13~ Is there a difference between, making love, having sex, and fucking?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
You know that I will be 100% truthful, so ask.
36~ What is your favorite time of day to have sex/make love?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
13- How about having a certain hair cut/style?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
That one or two things that made you go hmmmm, OMG or wow!
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
32- What's your greatest talent? Can I see it right now?
26~ What side of the bed do you sleep on?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
15- What's your favorite saying? What word or phrase is your least favorite?
How about if they talk dirty and/or call you names?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
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?
9- If you could have three wishes, what would they be? Why?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
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?
Get this wrong and this could mean the end… :-) some funny, some not…
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
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?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
10- What is your favorite family tradition? What’s your least favorite?
7- What are your thoughts on religion? Is there an afterlife?
30~ What's something unexpected that turns you on?
If you win, what will you make them do?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
51~ What tends to bring a smile to your face?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
42~ What’s your biggest regret in life?
*** Questions about Relationships/Past ***
4- For a pet, Cat, dog or other?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
1- What was your first impression of me? Has it changed?
15- What bad habit do you wish you could quit? Do you have any addictions?
(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…)
84~ How do you feel about reading/listening to adult stories?
Would /have you ever given your partner a lap dance and Striptease?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Any that are a turn off?
50~ How many children do you have? What are their ages?
Repairman/Lonely Wife Virgin/Experienced
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
62~ Have you used adult toys?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
17- What’s your favorite holiday? What’s your least favorite?
6- Do you have dreams? Can you remember them? What do you usually dream about?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
47~ What would be your dream job and why?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
22- What is your favorite childhood memory? What is your least favorite?
*** Deal Breaker Questions ***
If NO, would you ever have one? Would it be with 2 men or 2 women?
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?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
9~ How many times over your lifetime do you think you have had sex so far?
37- Do you like your name? If you could change it, what would you change it too?
Does the thought excite you? Care to share?
*** What’s Your Favorite…? ***
7- What if a person smells a certain way? 8- How about smoking?
How many partners have you had oral sex with? Who? 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~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
9- What’s your favorite season and why? What’s your least favorite?
28- What are some things that people do that irritate you?
Would you ever want to be woken up with oral and/or intercourse?
92~ Have you ever had or have an STD? How many? What was it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
12- What is the weirdest thing you've ever eaten?
What is your view on sex? Meaning, When/Where/ How often/
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
Would you allow me to clean every part of your body with my soapy hands and fingers?
19- Do/have you smoked? What do you prefer? How often?
17- Have you ever done drugs? Which ones? How often?
34~ Do you like the lights on or off during sex?
Doctor/Nurse Stripper/Client
14- What's your favorite dessert? Do you a 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,
46~ Have you ever used furniture, or other types of things to aid you while having sex?
5- Have you ever been hypnotized? Would you allow yourself to be?
19- What’s your favorite fairytale? What’s your least favorite?
29- How superstitious are you?
12- What’s your favorite food? What’s your least favorite?
What is your favorite toy? Ever wanted to try a specific toy?
29~ What are some things that turn you off? What is your biggest turn off?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
48~ Do you have any siblings? Are you close to your family?
13- What is the craziest/scariest thing you've ever done?
7-What do I do in bed that drives you wild? How about, what turns you off?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Nurse/Patient Celebrity/Fan
92~ Everyone needs a “safe” word. What is yours?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
14- What is an embarrassing moment in your life? How about your most embarrassing?
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?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What is your favorite position? Why?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
18- How often do you drink alcohol? What is your favorite drink?
Master/Slave Boss/Maid
Can you Deep Throat? Do you like the taste of yourself?
83~ How do you feel about Porn?
Do you think this brought you closer together?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Do you like it when they show and tell you what they want?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
How old are you? Male or Female?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
15~ Have you ever been “in love”? Who? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
What would you say to prove to yourself that it was really you?
If yes, what?
82~ Do you have any fantasies involving Role-Playing?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
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?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
40~ What’s the weirdest place you’ve ever had sex?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
What was the longest? What was the shortest?
51~ Are you willing to play adult games with your partner?
8- What's your favorite flavor of ice cream? Do you a least favorite?
7- What’s your favorite book? Do you have a favorite genre? Do you a 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.
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
49~ How many times have you been married? Why did they end?
45~ How do you feel about me blindfolding you? How about blindfolding me?
How well do you know me? And some of your thoughts about me
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
33- Beach or Mountains? Or is there another place to like better?
36- Do you play video games? What is your favorite? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
What have you learned about me that was new and/or surprising?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
*** Random Questions ***
Model/Photographer Police/Criminal
19~ Who/when was your first “heartbreak”?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
1- What’s your favorite animal? Do you a least favorite?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Do you have a favorite? Is it ok if your partner does?
If you say it, I will stop, and we can talk about it when you are ready.
18~ Who/when was your first “crush”?
65~ Describe the best orgasm you’ve ever had? Care to share?
What do you dislike about me? I asked you to be 100% honest.
3- What’s your favorite smell? Do you a least favorite?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? 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?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
23- What is your dream job? What was it as a child?
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)
Please share Did you stop?
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…
The Ice Breaker Questions
Would you read them together?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
60~ How important is oral sex? Do you like receiving? Do you like giving?
How many times do you think you have “made love”?
31- If given a chance to be immortal, would you take it? Why?
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?
8- What are your thoughts on politics?
38~ Share your most embarrassing sexual memory?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
5~ When you first started having sex, was it what you thought it would be?
What have you learned about yourself that you did not before this?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
10- List 5 of your top pet peeves.
Would you do it again, and would you rather 2 females or 2 males?