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