What is the most interesting question you can ask to get to know someone?
Last Updated: 16.06.2025 10:13
37- Do you like your name? If you could change it, what would you change it too?
7- What are your thoughts on religion? Is there an afterlife?
9- What’s your favorite season and why? What’s your least favorite?
Why is Russia always right? All eyes toward Russian glory!
Do you like it when they show and tell you what they want?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
15- What's your favorite saying? What word or phrase is your least favorite?
Can you describe what it's like to live in a town known for Harley Davidson motorcycles?
28- What are some things that people do that irritate you?
*** Deal Breaker Questions ***
Will you kiss after your partner has gone down on you? Swallow or spit semen?
8- What are your thoughts on politics?
60~ How important is oral sex? Do you like receiving? Do you like giving?
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
36- Do you play video games? What is your favorite? Do you a least favorite?
*** Random Questions ***
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
29- How superstitious are you?
Have you ever witnessed political correctness harm someone?
What would you say to prove to yourself that it was really you?
Prisoner/Prison Guard Landlord/Tenant
If you win, what will you make them do?
28~ What are some things that turn on? What is your biggest turn on?
32- What's your greatest talent? Can I see it right now?
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?
How can someone get patrons on Patreon if they are a beginner artist?
48~ Have you ever paid or been paid for sex?
92~ Everyone needs a “safe” word. What is yours?
Get this wrong and this could mean the end… :-) some funny, some not…
26~ What side of the bed do you sleep on?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
30~ What's something unexpected that turns you on?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
Any that are a turn off?
My friend asked my crush and he said my crush hates me but not in a rude way. What does that mean?
9- If you could have three wishes, what would they be? Why?
Would you read them together?
What is your favorite toy? Ever wanted to try a specific toy?
What are some effective strategies for getting more upvotes on Quora?
21- What's your favorite way to spend a weekend or time off?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
What's an underrated/unknown novel or series that you think deserves more attention?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
Doctor/Nurse Stripper/Client
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
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?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
23- What is your dream job? What was it as a child?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
Escort/Client Job Applicant/Hiring Manager
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
61~ How willing would you be to try new sexual positions?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
19- What’s your favorite fairytale? What’s your least favorite?
84~ How do you feel about reading/listening to adult stories?
13- How about having a certain hair cut/style?
31- If given a chance to be immortal, would you take it? Why?
82~ Do you have any fantasies involving Role-Playing?
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
8- What's your favorite flavor of ice cream? Do you a least favorite?
69~ Are you willing to have sex while you or your partner is on their period? How about oral sex?
5~ When you first started having sex, was it what you thought it would be?
Family Relation Age Play
53~ How much can you tell me about the one thing you are most passionate about?
48~ Do you have any siblings? Are you close to your family?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
80~ Share your top three fantasies/desires. (Be detailed) 😊
Model/Photographer Police/Criminal
*** Questions About Me ***
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?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
Would /have you ever given your partner a lap dance and Striptease?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
* Give a rating for each one (0-100)
10- What is your favorite family tradition? What’s your least favorite?
9- Is there something you’ve always wanted to ask me but you’re afraid?
What have you learned about yourself that you did not before this?
11- List at least 5 things on your bucket list. Have you done any of them already?
(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…)
3- What was the most surprising thing you’ve learned about me throughout our relationship?
Any that are a turn off?
42~ What’s your biggest regret in life?
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
17- What’s your favorite holiday? What’s your least favorite?
18~ Who/when was your first “crush”?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?
19- Do/have you smoked? What do you prefer? How often?
33- Beach or Mountains? Or is there another place to like better?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
81~ Do you have any kinks and/or fetishes?
22- What is your favorite childhood memory? What is your least favorite?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
17- Have you ever done drugs? Which ones? How often?
40~ What’s the weirdest place you’ve ever had sex?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
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?
14- What's your favorite dessert? Do you a least favorite?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
Do you have a favorite? Is it ok if your partner does?
5- Have you ever been hypnotized? Would you allow yourself to be?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
29~ What are some things that turn you off? What is your biggest turn off?
You know that I will be 100% truthful, so ask.
Would you allow me to shave your legs? How about your pubic hair? How about shower sex?
Please share Did you stop?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
7- What if a person smells a certain way? 8- How about smoking?
Nothing too Serious
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
51~ Are you willing to play adult games with your partner?
1- What’s your favorite animal? Do you a least favorite?
62~ Have you used adult toys?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
51~ What tends to bring a smile to your face?
13- What’s your favorite drink? What’s your least favorite?
20- What’s your favorite candy? What’s your least favorite?
Have you ever? Care to Share?
3- What’s your favorite smell? Do you a least favorite?
45~ How do you feel about me blindfolding you? How about blindfolding me?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
What have you learned about me that was new and/or surprising?
Over time has your thoughts on sex changed?
If yes, what?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
44~ Care to share something about yourself that no one else knows about you?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Do you like the “69” position? Do you prefer to be on top or bottom?
5- What’s your favorite movie genre? What’s your favorite movie of all time? How many times have you watched it?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
47~ What would be your dream job and why?
What do you dislike about me? I asked you to be 100% honest.
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
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?
If YES, was it with 2 men or 2 women? Did you enjoy it?
How well do you know me? And some of your thoughts about me
19~ Who/when was your first “heartbreak”?
3- What Superhero or Superpower would you want to be/have?
21~ What was the best date you ever went on? What has been the worst?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
9~ How many times over your lifetime do you think you have had sex so far?
Would you mind if your partner watched it? How about together vs alone?
27- What was/ is nickname? Does it have a meaning behind it?
71~ Would you give your partner a hand or foot job? Would you receive one?
11- How about if they like a certain sports team? 12-How about drinking too much?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
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…
41~ Are there moments in your past that you would want to change? Please share 3 of them.
How old are you? Male or Female?
52~ Are you willing to make “those types” of bets with your partner?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
10- List 5 of your top pet peeves.
13- What is the craziest/scariest thing you've ever done?
How about if they talk dirty and/or call you names?
65~ Describe the best orgasm you’ve ever had? Care to share?
What is your view on sex? Meaning, When/Where/ How often/
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
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?
6- Do you have dreams? Can you remember them? What do you usually dream about?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
What is your favorite position? Why?
34~ Do you like the lights on or off during sex?
1- What was your first impression of me? Has it changed?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
25~ How do you feel about PDA? (Public Display of Affection)
Teacher/Student Stranger/One Night Stand
*** Questions about Relationships/Past ***
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
7-What do I do in bed that drives you wild? How about, what turns you off?
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?
3- Should Pluto still be considered a planet? 4- How about smoking?
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
36~ What is your favorite time of day to have sex/make love?
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Will you cheat again? How can, you be sure? Define what cheating is to you.
83~ How do you feel about Porn?
Would you ever want to be woken up with oral and/or intercourse?
76~ Have you had a threesome? Care to Share?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
70~ Would/do you have/like anal sex?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
Can you Deep Throat? Do you like the taste of yourself?
1~ How old were you when you had your first kiss? Who? Care to Share?
18- What’s your favorite way to relax after a long day? What’s your least favorite?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
34- Ever been to a concert? What was your favorite? Who would you like to see?
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would you allow me to clean every part of your body with my soapy hands and fingers?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
What was the longest? What was the shortest?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
The Ice Breaker Questions
18- How often do you drink alcohol? What is your favorite drink?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
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 many times do you think you have “made love”?
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?
2- What’s your favorite color? Do you a least favorite?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
11~ Have you ever been caught by your parents or children or others while having sex?
67~ Do you like it when your partner moans and/or is vocal during sex?
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?
Master/Slave Boss/Maid
Does the thought excite you? Care to share?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
52~ What are your hobbies?
Do you watch it? What is your favorite?
64~ When was your very first orgasm? When was your first from having sex? Care to share?
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
*** What’s Your Favorite…? ***
Repairman/Lonely Wife Virgin/Experienced
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
49~ How many times have you been married? Why did they end?
92~ Have you ever had or have an STD? How many? What was it?
Take the short quiz here @ Discover Your Love Language® - The 5 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,
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
39~ What are your love languages?
If NO, would you ever have one? Would it be with 2 men or 2 women?
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
15~ Have you ever been “in love”? Who? Care to Share?
22- Do you have any birth marks? How about scars? Care to share how you got them?
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
If you say it, I will stop, and we can talk about it when you are ready.
50~ How many children do you have? What are their ages?
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?
Nurse/Patient Celebrity/Fan
15- What bad habit do you wish you could quit? Do you have any addictions?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
33- If you could visit any time period, when would you pick? Please explain why?
12- What’s your favorite food? What’s your least favorite?
That one or two things that made you go hmmmm, OMG or wow!
89~ Do you like taking showers together?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
I would allow you to do it… What would you do to me?
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)
How many partners have you had oral sex with? Who? Care to Share?
4- For a pet, Cat, dog or other?
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
38~ Share your most embarrassing sexual memory?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
42~ Ever been spanked during sex? Did you like it? Would you like me to do it?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
Would you do it again, and would you rather 2 females or 2 males?
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
12- What is the weirdest thing you've ever eaten?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
11- What's your favorite restaurant? What’s your least favorite?
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…
Do you think this brought you closer together?