What is the most interesting question you can ask to get to know someone?
Last Updated: 22.06.2025 03:26
3- What was the most surprising thing you’ve learned about me throughout our relationship?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
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?
What factors contributed to The Beatles' bitterness?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
48~ Have you ever paid or been paid for sex?
I would allow you to do it… What would you do to me?
What made you stop being an addict?
Nurse/Patient Celebrity/Fan
What have you learned about yourself that you did not before this?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
1~ How old were you when you had your first kiss? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
48~ Do you have any siblings? Are you close to your family?
Would you do it again, and would you rather 2 females or 2 males?
What would you say to prove to yourself that it was really you?
*** What’s Your Favorite…? ***
9- What’s your favorite season and why? What’s your least favorite?
13~ Is there a difference between, making love, having sex, and fucking?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
Skin Aging Reduced by Molecules from Bacteria in the Blood - Neuroscience News
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
51~ What tends to bring a smile to your face?
Any that are a turn off?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
After a series of tumors, woman’s odd-looking tongue explains everything - Ars Technica
8- What's your favorite flavor of ice cream? Do you a least favorite?
7- What are your thoughts on religion? Is there an afterlife?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
What are the common formulas for improvising ornaments in bel canto singing?
12- What is the weirdest thing you've ever eaten?
13- How about having a certain hair cut/style?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
Has anyone ever participated in a gang bang and what was it like?
34~ Do you like the lights on or off during sex?
11- List at least 5 things on your bucket list. Have you done any of them already?
11- How about if they like a certain sports team? 12-How about drinking too much?
What kind of book did you write after turning 55?
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Repairman/Lonely Wife Virgin/Experienced
What’s the best way to monetize email subscribers?
52~ What are your hobbies?
84~ How do you feel about reading/listening to adult stories?
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…
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
1- What’s your favorite animal? Do you a least favorite?
How well do you know me? And some of your thoughts about me
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
What’s the longest time you gone without having sex, after, having it? How much time between the others?
If you win, what will you make them do?
33- If you could visit any time period, when would you pick? Please explain why?
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?
14- What's your favorite dessert? 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)
*** Deal Breaker Questions ***
Do you like the “69” position? Do you prefer to be on top or bottom?
27- What was/ is nickname? Does it have a meaning behind it?
3- What Superhero or Superpower would you want to be/have?
23- What is your dream job? What was it as a child?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
32- What's your greatest talent? Can I see it right now?
Does the thought excite you? Care to share?
You know that I will be 100% truthful, so ask.
89~ Do you like taking showers together?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
82~ Do you have any fantasies involving Role-Playing?
Prisoner/Prison Guard Landlord/Tenant
Model/Photographer Police/Criminal
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
That one or two things that made you go hmmmm, OMG or wow!
64~ When was your very first orgasm? When was your first from having sex? Care to share?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
13- What is the craziest/scariest thing you've ever done?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
11~ Have you ever been caught by your parents or children or others while having sex?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
42~ What’s your biggest regret in life?
If YES, was it with 2 men or 2 women? Did you enjoy it?
80~ Share your top three fantasies/desires. (Be detailed) 😊
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?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
6- Do you have dreams? Can you remember them? What do you usually dream about?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
40~ What’s the weirdest place you’ve ever had sex?
Would you read them together?
Family Relation Age Play
51~ Are you willing to play adult games with your partner?
Doctor/Nurse Stripper/Client
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
49~ How many times have you been married? Why did they end?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
17- Have you ever done drugs? Which ones? How often?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
(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…)
37- Do you like your name? If you could change it, what would you change it too?
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?
12- What’s your favorite food? What’s your least favorite?
7-What do I do in bed that drives you wild? How about, what turns you off?
7- What if a person smells a certain way? 8- How about smoking?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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,
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
9- Is there something you’ve always wanted to ask me but you’re afraid?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
44~ Care to share something about yourself that no one else knows about you?
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?
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?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Escort/Client Job Applicant/Hiring Manager
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?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
34- Ever been to a concert? What was your favorite? Who would you like to see?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
92~ Have you ever had or have an STD? How many? What was it?
28- What are some things that people do that irritate you?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
If you say it, I will stop, and we can talk about it when you are ready.
47~ What would be your dream job and why?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
2- What’s your favorite color? Do you a least favorite?
3- What’s your favorite smell? Do you a least favorite?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
28~ What are some things that turn on? What is your biggest turn on?
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?
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
The Ice Breaker Questions
13- What’s your favorite drink? What’s your least favorite?
61~ How willing would you be to try new sexual positions?
Would you allow me to clean every part of your body with my soapy hands and fingers?
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
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?
If NO, would you ever have one? Would it be with 2 men or 2 women?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
21~ What was the best date you ever went on? What has been the worst?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
3- Should Pluto still be considered a planet? 4- How about smoking?
76~ Have you had a threesome? Care to Share?
70~ Would/do you have/like anal sex?
How about if they talk dirty and/or call you names?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
26~ What side of the bed do you sleep on?
71~ Would you give your partner a hand or foot job? Would you receive one?
Any that are a turn off?
1- What was your first impression of me? Has it changed?
5~ When you first started having sex, was it what you thought it would be?
83~ How do you feel about Porn?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Do you think this brought you closer together?
Get this wrong and this could mean the end… :-) some funny, some not…
62~ Have you used adult toys?
25~ How do you feel about PDA? (Public Display of Affection)
18~ Who/when was your first “crush”?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
Will you cheat again? How can, you be sure? Define what cheating is to you.
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
36- Do you play video games? What is your favorite? Do you a least favorite?
24~ What are your expectations in a relationship? (I know a very big question, take your time)
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
What do you dislike about me? I asked you to be 100% honest.
Do you watch it? What is your favorite?
33- Beach or Mountains? Or is there another place to like better?
How many times do you think you have “made love”?
15- What bad habit do you wish you could quit? Do you have any addictions?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
Would you ever want to be woken up with oral and/or intercourse?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
If yes, what?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Over time has your thoughts on sex changed?
10- List 5 of your top pet peeves.
45~ How do you feel about me blindfolding you? How about blindfolding me?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
8- What are your thoughts on politics?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
5- Have you ever been hypnotized? Would you allow yourself to be?
10- What is your favorite family tradition? What’s your least favorite?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
*** Questions About Me ***
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
Master/Slave Boss/Maid
Would you mind if your partner watched it? How about together vs alone?
17- What’s your favorite holiday? What’s your 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?
*** Random Questions ***
29~ What are some things that turn you off? What is your biggest turn off?
50~ How many children do you have? What are their ages?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
10~ How many dates are necessary before you to have sex with someone?
Would /have you ever given your partner a lap dance and Striptease?
Have you ever? Care to Share?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
What is your favorite position? Why?
39~ What are your love languages?
Teacher/Student Stranger/One Night Stand
60~ How important is oral sex? Do you like receiving? Do you like giving?
14- What is an embarrassing moment in your life? How about your most embarrassing?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
19~ Who/when was your first “heartbreak”?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
* Give a rating for each one (0-100)
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Can you Deep Throat? Do you like the taste of yourself?
Nothing too Serious
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
4- For a pet, Cat, dog or other?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
22- What is your favorite childhood memory? What is your least favorite?
67~ Do you like it when your partner moans and/or is vocal during sex?
How old are you? Male or Female?
81~ Do you have any kinks and/or fetishes?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
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…
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
15~ Have you ever been “in love”? Who? Care to Share?
*** Questions about Relationships/Past ***
What is your favorite toy? Ever wanted to try a specific toy?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
How many partners have you had oral sex with? Who? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
19- Do/have you smoked? What do you prefer? How often?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
What have you learned about me that was new and/or surprising?
21- What's your favorite way to spend a weekend or time off?
18- How often do you drink alcohol? What is your favorite drink?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
15- What's your favorite saying? What word or phrase is your least favorite?
65~ Describe the best orgasm you’ve ever had? Care to share?
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)?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
19- What’s your favorite fairytale? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
29- How superstitious are you?
Please share Did you stop?
38~ Share your most embarrassing sexual memory?
9~ How many times over your lifetime do you think you have had sex so far?
52~ Are you willing to make “those types” of bets with your partner?
Do you have a favorite? Is it ok if your partner does?
What is your view on sex? Meaning, When/Where/ How often/
What was the longest? What was the shortest?
30~ What's something unexpected that turns you on?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
Do you shave/trim your pubic hair? For you guys do you shave your balls?
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
9- If you could have three wishes, what would they be? Why?
Do you like it when they show and tell you what they want?
92~ Everyone needs a “safe” word. What is yours?
11- What's your favorite restaurant? What’s your least favorite?