What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 01:49
8- What's your favorite flavor of ice cream? Do you a least favorite?
Please share Did you stop?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
How might an Indian girl respond to someone saying "I love you"?
81~ Do you have any kinks and/or fetishes?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
Did you become a cuckold for your wife?
92~ Everyone needs a “safe” word. What is yours?
14- What is an embarrassing moment in your life? How about your most embarrassing?
28~ What are some things that turn on? What is your biggest turn on?
Nurse/Patient Celebrity/Fan
3- What’s your favorite smell? 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?
Master/Slave Boss/Maid
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
14- What's your favorite dessert? Do you a least favorite?
If Iran’s Oil Is Cut Off, China Will Pay the Price - WSJ
23- What is your dream job? What was it as a child?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
8- What are your thoughts on politics?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
What are some things that normal people do that religious people call sins?
What is your view on sex? Meaning, When/Where/ How often/
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
Why does a narcissist act like it's nothing when they hurt you?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
29~ What are some things that turn you off? What is your biggest turn off?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
Why is the Middle East prone to terrorism?
Have you ever? Care to Share?
51~ What tends to bring a smile to your face?
40~ What’s the weirdest place you’ve ever had sex?
Forget Florida — these two unexpected states are the new retirement hot spots - Yahoo Finance
If YES, was it with 2 men or 2 women? Did you enjoy it?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
70~ Would/do you have/like anal sex?
Why are white women so overly emotional?
76~ Have you had a threesome? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
36~ What is your favorite time of day to have sex/make love?
Can you turn 150 pages into a 5 minute presentation before a meeting?
5~ When you first started having sex, was it what you thought it would be?
1~ How old were you when you had your first kiss? Who? Care to Share?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
What is the reason behind the Russian government's negative view on foreign travel?
13- What is the craziest/scariest thing you've ever done?
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?
What do you dislike about me? I asked you to be 100% honest.
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
4- For a pet, Cat, dog or other?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
31- If given a chance to be immortal, would you take it? Why?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
1- What’s your favorite animal? Do you a least favorite?
Would /have you ever given your partner a lap dance and Striptease?
17- Have you ever done drugs? Which ones? How often?
What is your favorite position? Why?
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…
62~ Have you used adult toys?
19- Do/have you smoked? What do you prefer? How often?
Can you Deep Throat? Do you like the taste of yourself?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
I would allow you to do it… What would you do to me?
18~ Who/when was your first “crush”?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
65~ Describe the best orgasm you’ve ever had? 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?
52~ Are you willing to make “those types” of bets with your partner?
17- What’s your favorite holiday? 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?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
52~ What are your hobbies?
30~ What's something unexpected that turns you on?
Nothing too Serious
34~ Do you like the lights on or off during sex?
*** Questions About Me ***
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
48~ Have you ever paid or been paid for sex?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
9~ How many times over your lifetime do you think you have had sex so far?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
Would you ever want to be woken up with oral and/or intercourse?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
2- What’s your favorite color? Do you a least favorite?
Do you like the “69” position? Do you prefer to be on top or bottom?
The Ice Breaker Questions
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
13- How about having a certain hair cut/style?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
38~ Share your most embarrassing sexual memory?
51~ Are you willing to play adult games with your partner?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
89~ Do you like taking showers together?
25~ How do you feel about PDA? (Public Display of Affection)
22- Do you have any birth marks? How about scars? Care to share how you got them?
60~ How important is oral sex? Do you like receiving? Do you like giving?
19- What’s your favorite fairytale? What’s your least favorite?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Will you cheat again? How can, you be sure? Define what cheating is to you.
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
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…
11~ Have you ever been caught by your parents or children or others while having sex?
* Give a rating for each one (0-100)
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
26~ What side of the bed do you sleep on?
Doctor/Nurse Stripper/Client
Model/Photographer Police/Criminal
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
*** What’s Your Favorite…? ***
24~ What are your expectations in a relationship? (I know a very big question, take your time)
Would you do it again, and would you rather 2 females or 2 males?
*** Deal Breaker Questions ***
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
10- What is your favorite family tradition? What’s your least favorite?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
50~ How many children do you have? What are their ages?
45~ How do you feel about me blindfolding you? How about blindfolding me?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
(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…)
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
How many partners have you had oral sex with? Who? Care to Share?
Do you think this brought you closer together?
Does the thought excite you? Care to share?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
Family Relation Age Play
How well do you know me? And some of your thoughts about me
15- What's your favorite saying? What word or phrase is your least favorite?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
Do you like it when they show and tell you what they want?
9- If you could have three wishes, what would they be? Why?
Would you mind if your partner watched it? How about together vs alone?
82~ Do you have any fantasies involving Role-Playing?
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?
7-What do I do in bed that drives you wild? How about, what turns you off?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
9- Is there something you’ve always wanted to ask me but you’re afraid?
That one or two things that made you go hmmmm, OMG or wow!
Would you read them together?
10~ How many dates are necessary before you to have sex with someone?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Prisoner/Prison Guard Landlord/Tenant
28- What are some things that people do that irritate you?
11- List at least 5 things on your bucket list. Have you done any of them already?
Do you watch it? What is your favorite?
37- Do you like your name? If you could change it, what would you change it too?
*** Random Questions ***
5- Have you ever been hypnotized? Would you allow yourself to be?
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?
61~ How willing would you be to try new sexual positions?
3- What Superhero or Superpower would you want to be/have?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
Do you shave/trim your pubic hair? For you guys do you shave your balls?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
If you win, what will you make them do?
29- How superstitious are you?
Any that are a turn off?
19~ Who/when was your first “heartbreak”?
18- How often do you drink alcohol? What is your favorite drink?
13- What’s your favorite drink? What’s your least favorite?
39~ What are your love languages?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
67~ Do you like it when your partner moans and/or is vocal during sex?
Repairman/Lonely Wife Virgin/Experienced
48~ Do you have any siblings? Are you close to your family?
Teacher/Student Stranger/One Night Stand
How many times do you think you have “made love”?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
49~ How many times have you been married? Why did they end?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
34- Ever been to a concert? What was your favorite? Who would you like to see?
92~ Have you ever had or have an STD? How many? What was it?
You know that I will be 100% truthful, so ask.
Get this wrong and this could mean the end… :-) some funny, some not…
How old are you? Male or Female?
32- What's your greatest talent? Can I see it right now?
27- What was/ is nickname? Does it have a meaning behind it?
21~ What was the best date you ever went on? What has been the worst?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
12- What’s your favorite food? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
If NO, would you ever have one? Would it be with 2 men or 2 women?
42~ What’s your biggest regret in life?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Any that are a turn off?
What was the longest? What was the shortest?
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?
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’s the longest time you gone without having sex, after, having it? How much time between the others?
11- What's your favorite restaurant? What’s your least favorite?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
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?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
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)
Do you have a favorite? Is it ok if your partner does?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
33- If you could visit any time period, when would you pick? Please explain why?
7- What are your thoughts on religion? Is there an afterlife?
47~ What would be your dream job and why?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
83~ How do you feel about Porn?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
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?
15~ Have you ever been “in love”? Who? Care to Share?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
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?
*** Questions about Relationships/Past ***
15- What bad habit do you wish you could quit? Do you have any addictions?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Over time has your thoughts on sex changed?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
If yes, what?
33- Beach or Mountains? Or is there another place to like better?
What have you learned about me that was new and/or surprising?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
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?
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?
11- How about if they like a certain sports team? 12-How about drinking too much?
What have you learned about yourself that you did not before this?
If you say it, I will stop, and we can talk about it when you are ready.
10- List 5 of your top pet peeves.
Would you allow me to clean every part of your body with my soapy hands and fingers?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
22- What is your favorite childhood memory? What is your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
What would you say to prove to yourself that it was really you?
9- What’s your favorite season and why? What’s your least favorite?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
44~ Care to share something about yourself that no one else knows about you?
53~ How much can you tell me about the one thing you are most passionate about?
How about if they talk dirty and/or call you names?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
What is your favorite toy? Ever wanted to try a specific toy?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
7- What if a person smells a certain way? 8- How about smoking?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
36- Do you play video games? What is your favorite? Do you a least favorite?
1- What was your first impression of me? Has it changed?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
21- What's your favorite way to spend a weekend or time off?