What is the most interesting question you can ask to get to know someone?
Last Updated: 19.06.2025 06:23
51~ Are you willing to play adult games with your partner?
42~ What’s your biggest regret in life?
21~ What was the best date you ever went on? What has been the worst?
Is there a smell that most people do not like that you do? Is there a smell that triggers a memory?
* Which of the following turns you on the most? Do you have any not on this list? Care to share?
If YES, was it with 2 men or 2 women? Did you enjoy it?
What are 10 interesting facts about you?
If NO, would you ever have one? Would it be with 2 men or 2 women?
10- What is your favorite family tradition? What’s your least favorite?
34- Ever been to a concert? What was your favorite? Who would you like to see?
92~ Everyone needs a “safe” word. What is yours?
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?
63~ Is having an orgasm important every time you have sex? Have you ever faked an orgasm?
Take the short quiz here @ Discover Your Love Language® - The 5 Love Languages®
38- If you won the Lottery and got 200 million dollars, what would you do with all that money?
38~ Share your most embarrassing sexual memory?
Is it possible to revive a dead person in real life with black magic?
40~ What’s the weirdest place you’ve ever had sex?
44~ Care to share something about yourself that no one else knows about you?
10- List 5 of your top pet peeves.
Why do many women wear sleeveless shirts, more so than men?
41~ Are there moments in your past that you would want to change? Please share 3 of them.
27- What was/ is nickname? Does it have a meaning behind it?
Do you like the “69” position? Do you prefer to be on top or bottom?
Why does the God of the Bible condemn homosexual acts?
7-What do I do in bed that drives you wild? How about, what turns you off?
47~ Have you ever thought about trying tantric sex? (Not sure? Look it up)
6- Is there anything that I do/say that irritates you? How about makes you smile and love to hear it?
Why is there so much free porn on the internet?
6- Do you have dreams? Can you remember them? What do you usually dream about?
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?
What is your view on sex? Meaning, When/Where/ How often/
What are the best self-care practices to improve mental health?
12~ Have you ever had a one-nightstand? Was it good, fun, satisfying? Would you do it again?
15- What's your favorite saying? What word or phrase is your least favorite?
Nurse/Patient Celebrity/Fan
Why is it that women are stronger than men nowadays?
22- Do you have any birth marks? How about scars? Care to share how you got them?
28- What are some things that people do that irritate you?
That one or two things that made you go hmmmm, OMG or wow!
How did you as a human being change while growing up?
43~ If you could write up to a one-page letter to yourself, what would you say and what age would you send it?
79~ How important is it to have a partner that will help and encourage you to fulfill your fantasies and desires?
52~ Are you willing to make “those types” of bets with your partner?
How is TikTok able to censor porn?
7- What if a person smells a certain way? 8- How about smoking?
7~ How many times in one day have you had sex? Who/When/Where? Care to Share?
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)
9- Is there something you’ve always wanted to ask me but you’re afraid?
50~ How many children do you have? What are their ages?
If yes, what?
4~ How old were you when you lost your virginity? Is it a good memory? Who? Care to Share? (be detailed)
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?
Will you kiss after your partner has gone down on you? Swallow or spit semen?
11~ Have you ever been caught by your parents or children or others while having sex?
14~ When was the first time you said, “I Love You”? (romantically) Did you mean it? Who? Care to Share?
13- What is the craziest/scariest thing you've ever done?
5- Do you fold or scrunch? (toilet paper while you wipe) 6- How about bad hygiene?
Will you cheat again? How can, you be sure? Define what cheating is to you.
8- What's something unexpected that turns you on that I do to you? Don’t be shy now, I really want to know.
51~ What tends to bring a smile to your face?
47~ What would be your dream job and why?
29- How superstitious are 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?
Meaning if you ever say it no matter how long we have been together or where we are in the moment…
64~ When was your very first orgasm? When was your first from having sex? Care to share?
20~ Have you ever cheated? Care to Share? If you have, why do you believe that you did?
17~ What is the average length of your relationship(s)? What was the longest? Why did they end?
61~ How willing would you be to try new sexual positions?
You know that I will be 100% truthful, so ask.
60~ How important is oral sex? Do you like receiving? Do you like giving?
7- What’s your favorite book? Do you have a favorite genre? Do you a least favorite?
26~ What side of the bed do you sleep on?
How well do you know me? And some of your thoughts about me
I would allow you to do it… What would you do to me?
36~ What is your favorite time of day to have sex/make love?
62~ Have you used adult toys?
82~ Do you have any fantasies involving Role-Playing?
How many partners have you had oral sex with? Who? Care to Share?
13~ Is there a difference between, making love, having sex, and fucking?
56~ Would you ever go to a strip club with your partner? Have you ever been? Care to Share?
*** Questions About Me ***
92~ Have you ever had or have an STD? How many? What was it?
33- Beach or Mountains? Or is there another place to like better?
What would you say to prove to yourself that it was really you?
73~ Have you ever had public sex? Care to share? Have you ever had an orgasm in a public place?
How many times do you think you have “made love”?
3- What Superhero or Superpower would you want to be/have?
If you say it, I will stop, and we can talk about it when you are ready.
74~ Have you ever had sex while others watched? Have you ever watched others have sex?
Can you have multiple orgasms? Are you able to have different kinds of orgasms?
44~ Have you ever been tied up during sex? What are your thoughts on bondage?
87~ Do you like it when I used my teeth (lightly)? How do you feel about hickeys?
13- How about having a certain hair cut/style?
1- What was your first impression of me? Has it changed?
49~ How many times have you been married? Why did they end?
Any that are a turn off?
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 shave your legs? How about your pubic hair? How about shower sex?
Get this wrong and this could mean the end… :-) some funny, some not…
What have you learned about me that was new and/or surprising?
32~ What are your favorite foreplay activities? Kissing/Touching? Food? Toys? Role Play? Others?
Have you ever? Care to Share?
71~ Would you give your partner a hand or foot job? Would you receive one?
12- What’s your favorite food? What’s your least favorite?
11- How about if they like a certain sports team? 12-How about drinking too much?
Do you shave/trim your pubic hair? For you guys do you shave your balls?
33~ Share your thoughts on what you believe great sex/love making is to you? How long should it last?
31- If given a chance to be immortal, would you take it? Why?
20- What’s your favorite candy? What’s your least favorite?
36- Do you play video games? What is your favorite? Do you a least favorite?
77~ What are your thoughts on swapping or swinging or group sex? Have you ever? Care to Share?
14 – Is it ok to talk to you while you are on the toilet? 15- Is it ok to eat while on the toilet?
37- Do you like your name? If you could change it, what would you change it too?
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…
2- Are you afraid of anything? (Spiders, heights, snakes, etc.) What is your greatest fear?
Master/Slave Boss/Maid
What was the longest? What was the shortest?
6- What’s your favorite TV series? Do you have a favorite genre? Do you a least favorite?
Escort/Client Job Applicant/Hiring Manager
18- What’s your favorite way to relax after a long day? What’s your least favorite?
11- List at least 5 things on your bucket list. Have you done any of them already?
20- Do you have any tattoos? Are there any you want? Are there any you find sexy/attractive?
81~ Do you have any kinks and/or fetishes?
How do you feel about anal play? (Fingers, toys, butt plug) How do you feel about rimming? (licking)
*** What’s Your Favorite…? ***
48~ Have you ever paid or been paid for sex?
90~ Have you ever had sex in a Pool or Hot Tub? Would you?
What have you learned about yourself that you did not before this?
19~ Who/when was your first “heartbreak”?
2- What do you remember about our first date? Rate it. Rate our first kiss. Rate our first time together.
8~ How many times a week would you like to engage in sexual activities? What is the average for you now?
How long for foreplay? Do you need to have an orgasm? Is afterplay important?
35~ Do you like playing music in the background or silence? Is there a sexy song that tends to get you in the mood?
68~ Would you ever get your partner up from bed by using oral sex and/or intercourse?
Do you think this brought you closer together?
88~ Do you prefer me to be naked or in lingerie, PJ’s when you are sleeping?
2- What’s your favorite color? Do you a least favorite?
8- What's your favorite flavor of ice cream? Do you a least favorite?
72~ Is it ok to ejaculate on your body, face, ass, breast? How about in your mouth? Is there any place not allowed?
Do you watch it? What is your favorite?
52~ What are your hobbies?
If you lose, are you willing to be their sex slave for a day, (anything goes)?
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?
Does the thought excite you? Care to share?
21- Do you have any piercings? Are there any you want? Are there any you find sexy/attractive?
24- What celebrities would you use your hall pass on? How about just dinner, or just hanging out with you?
*** Random Questions ***
34~ Do you like the lights on or off during sex?
30- Do you prefer living in the countryside, in a town, or in a big city? Why?
Prisoner/Prison Guard Landlord/Tenant
31~ What do you find most attractive sexually and non-sexually in a man/woman? (Body and Personality)
48~ Do you have any siblings? Are you close to your family?
Doctor/Nurse Stripper/Client
6~ How many sexual partners have you had? Can you name them all? Can you remember when and where?
How about if they talk dirty and/or call you names?
28~ What are some things that turn on? What is your biggest turn on?
37~ What is the biggest age gap between you and one of your sexual partners? Who? Care to Share?
16- What’s your favorite vacation you have been on? What’s your least favorite? Where would you like to go?
22- What is your favorite childhood memory? What is your least favorite?
Over time has your thoughts on sex changed?
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?
32- What's your greatest talent? Can I see it right now?
9~ How many times over your lifetime do you think you have had sex so far?
84~ How do you feel about reading/listening to adult stories?
(Strip poker, truth or dare, spin the bottle, Naked Twister, adult card games Etc.) Have you ever? Care to Share?
Piecing, tattoo, color hair, dress up a certain way, it could be anything… Shave me…
16- Can we talk about your health history? Have you had any surgeries? Any broken bones?
22~ What is the best pickup line anyone has ever used on you? What was the worst?
Would you ever want to be woken up with oral and/or intercourse?
Would/have you gotten a lap dance? Would/have you watched your partner get a lap dance?
35- Do you like playing board or cards game? What is your favorite? Do you a least favorite?
What’s the longest time you gone without having sex, after, having it? How much time between the others?
3~ How old were you when you got to 3rd base? (Touching and stimulating the genitals. Oral sex)
24~ What are your expectations in a relationship? (I know a very big question, take your time)
How old are you? Male or Female?
*** Questions about Relationships/Past ***
55~ Would you ever go to a nude beach/resort with your partner? Have you ever been? Care to Share?
46~ Have you ever used furniture, or other types of things to aid you while having sex?
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?
23- What is your dream job? What was it as a child?
39~ What are your love languages?
Can you Deep Throat? Do you like the taste of yourself?
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?
25~ How do you feel about PDA? (Public Display of Affection)
46~ Where do you want to be in your life in a year? How about 5 years? How about 10 years?
3- What was the most surprising thing you’ve learned about me throughout our relationship?
76~ Have you had a threesome? Care to Share?
7- What are your thoughts on religion? Is there an afterlife?
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,
4- What’s your favorite genre of music? What’s your least favorite? Is there a song that triggers a memory?
What is your favorite position? Why?
* Give a rating for each one (0-100)
Would /have you ever given your partner a lap dance and Striptease?
8- What are your thoughts on politics?
45~ What do you like about yourself? Rate yourself 1-10. (Looks, personality, etc....)
66~ What’s the shortest time it’s ever taken for you to have an orgasm? And the longest?
Teacher/Student Stranger/One Night Stand
27~ If you could freeze your body but not your mind at a certain age, what age would you be? Explain why.
57~ Describe the perfect penis/vagina. Does size really matter? What is too big/small?
Would you do it again, and would you rather 2 females or 2 males?
(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…)
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…
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?
Would you mind if your partner watched it? How about together vs alone?
30~ What's something unexpected that turns you on?
Do you like it when they show and tell you what they want?
43~ Ever had your hair pulled during sex? Did you like it? Would you like me to do it?
45~ How do you feel about me blindfolding you? How about blindfolding me?
19- Do/have you smoked? What do you prefer? How often?
15~ Have you ever been “in love”? Who? Care to Share?
Foot fetishes, Role-playing, Sadism, Masochism, Bondage, Discipline, Dominance and submission, Voyeurism, Exhibitionism, Furries, Humiliation, Gender/Age play, Cuckolding, Gagging, etc.?
29~ What are some things that turn you off? What is your biggest turn off?
89~ Do you like taking showers together?
13- What’s your favorite drink? What’s your least favorite?
3- Should Pluto still be considered a planet? 4- How about smoking?
Physical Touch - Words of Affirmation - Quality Time - Acts of Service - Receiving Gifts
5- Have you ever been hypnotized? Would you allow yourself to be?
54~ Would you ever go skinny dipping with your partner? Have you ever been? Care to Share?
10- Do I have a habit or quirk that you find cute or weird? How about an annoying habit of mine?
*** Deal Breaker Questions ***
Repairman/Lonely Wife Virgin/Experienced
1~ How old were you when you had your first kiss? Who? Care to Share?
12- What is the weirdest thing you've ever eaten?
65~ Describe the best orgasm you’ve ever had? Care to share?
1- What’s your (zodiac, astrological) sign? Do you believe this has any meaning in your life?
9- If you could have three wishes, what would they be? Why?
Nothing too Serious
14- What's your favorite dessert? Do you a least favorite?
83~ How do you feel about Porn?
4- For a pet, Cat, dog or other?
9- What’s your favorite season and why? What’s your least favorite?
Any that are a turn off?
10~ How many dates are necessary before you to have sex with someone?
18- How often do you drink alcohol? What is your favorite drink?
58~ Have you ever taken Nude or Hard-core photos and/or videos? Care to Share?
14- What is an embarrassing moment in your life? How about your most embarrassing?
91~ Would you ever go into an adult book/toys store with me? Would you buy something?
78~ Have you ever thought about making out or having sex with someone of the same sex? Care to Share?
Do you prefer your partner’s pubic hair trimmed, Landing Strip, full bush or completely bare?
1- Down the back or over the top? (The toilet paper roll) 2- Up or down? (The toilet seat)
Would you read them together?
The Ice Breaker Questions
What do you dislike about me? I asked you to be 100% honest.
Family Relation Age Play
17- Have you ever done drugs? Which ones? How often?
70~ Would/do you have/like anal sex?
4- What do you like about me? Rate me 1-10. (Looks, personality, overall, etc....)
19- What’s your favorite fairytale? What’s your least favorite?
Do you have a favorite? Is it ok if your partner does?
25- Fight, Flight, or Freeze? What is your typical response? Does it change with different settings?
Are you willing to help and encourage your partner to fulfill their fantasies and desires?
5~ When you first started having sex, was it what you thought it would be?
49~ If you could, would you want to be the opposite sex for a day, week, or year?
15- What bad habit do you wish you could quit? Do you have any addictions?
3- What’s your favorite smell? Do you a least favorite?
39~ Share your top three favorite/best memorable sexual experiences. Want to repeat them?
33- If you could visit any time period, when would you pick? Please explain why?
93~ Now that this really long questionnaire is over, one last question, ok maybe 3…
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?
16~ Do you believe in “soulmates”? Have you found yours? Who? Care to Share?
26- Do you cry while watching a movie or TV show? Which one did you cry the hardest?
If you win, what will you make them do?
17- What’s your favorite holiday? What’s your least favorite?
Is it ok for a man to perform oral sex after he has ejaculated inside of you?
Model/Photographer Police/Criminal
11- What's your favorite restaurant? What’s your least favorite?
18~ Who/when was your first “crush”?
5- What do I do outside the bedroom that turns you on? How about, what turns you off?
Please share Did you stop?
Would you allow me to clean every part of your body with my soapy hands and fingers?
53~ How about wearing no panties or bra at all, while wearing a dress or skirt? How about stockings and Garter Belts?
If yes, what kind? (Clitoral, Vaginal, G-Spot. Anal, Squirting, A-Spot, Cervix, Breast/Nipple, Touching, non- Touching/Mental)
What is your favorite toy? Ever wanted to try a specific toy?
67~ Do you like it when your partner moans and/or is vocal during sex?
1- What’s your favorite animal? 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?
80~ Share your top three fantasies/desires. (Be detailed) 😊
53~ How much can you tell me about the one thing you are most passionate about?
9- How about not brushing their teeth or having bad breath? 10- How about if they cuss too much?